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Asundexian
Asundexian
CAS 2064121-65-7
MW 592.9 g/mol, C26H21ClF4N6O4
4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxo-1-pyridinyl]butanoyl]amino]-2-fluorobenzamide
- (S)-4-(2-(4-(5-Chloro-2-(4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)phenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)butanamido)-2-fluorobenzamide
- 4-[[(2~{S})-2-[4-[5-chloranyl-2-[4-(trifluoromethyl)-1,2,3-triazol-1-yl]phenyl]-5-methoxy-2-oxidanylidene-pyridin-1-yl]butanoyl]amino]-2-fluoranyl-benzamide
- (S)-4-[2-[4-[5-Chloro-2-[4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1(2H)-yl]butanamido]-2-fluorobenzamide
APPROVALS 2026, FDA 2026, Sunharbo, LA585UM8DE, BAY2433334, BAY 2433334
To reduce the risk of stroke in adults following a recent mild-to-moderate non-cardioembolic ischemic stroke or a high-risk transient ischemic attack
Asundexian, sold under the brand name Sunharbo, is a Factor XIa inhibitor developed by Bayer to prevent stroke.[1][2]
Clinical trials
Asundexian efficacy and safety in patients have been evaluated in two clinical trial programs: phase IIb PACIFIC and phase III OCEANIC.[3] In the phase IIb PACIFIC clinical trial programs, asundexian consistently showed no difference in bleeding rate compared with placebo[4][5] and reduced the risk of bleeding compared with apixaban.[6] All three trials in the programs were not powered to show efficacy of asundexian.[3] However, a phase III trial, OCEANIC-AF, demonstrated a hazard ratio of 3.8 for stroke or systemic embolism with asundexian vs apixaban, so it was stopped due to a “lack of efficacy.” The remaining active study OCEANIC-STROKE was recommended to continue as planned. Bayer is reevaluating the design of the OCEANIC-AFINA based on the findings of the OCEANIC trial.[7]
In February 2026, the OCEANIC-STROKE trial was completed. This was a multicentre, randomised, double-blind, placebo-controlled study involving 12,000 people worldwide who had suffered a non-cardioembolic ischaemic stroke or a transient ischaemic attack. The trial revealed a 26% reduction in the rate of recurrence without major bleeding, a typical complication of antithrombotic drugs.[8][9][10]
SYN
US20180194745 – Substituted oxopyridine derivatives
Example 235
4-({(2S)-2-[4-{5-Chloro-2-[4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenyl}-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)-2-fluorobenzamide (Enantiomer 2)
| Separating method: column: Chiralpak AD-H SFC, 5 μm 250 mm×20 mm; mobile phase: carbon dioxide 75%/ethanol 25%; temperature: 40° C.; flow rate: 80 ml/min; pressure: 100 bar; UV detection: 210 nm. |
| Analysis: column: Daicel AD SFC 3 μm, 100 mm×4.6 mm; mobile phase: 75% carbon dioxide, 25% ethanol; flow rate: 3 ml/min; UV detection: 210 nm. |
SYN1
MEDKOO
Synthetic Reference
Design and Preclinical Characterization Program toward Asundexian (BAY 2433334), an Oral Factor XIa Inhibitor for the Prevention and Treatment of Thromboembolic Disorders
By: Roehrig, Susanne; et al
Journal of Medicinal Chemistry (2023), 66(17), 12203-12224
SYN2
Synthetic Reference
Study on Preparation Process of Anticoagulant BAY2433334
By: Zeng, Yanqun; et al
Molecules (2024), 29(24), 6039
SYN3
Synthetic Reference
Preparation of triazole containing oxopyridine derivative and its application in medicine
Assignee: Tianjin Institute of Pharmaceutical Research Co., Ltd.
Inventors: Wei, Qunchao; et al
China
Patent#CN116903585 A
SYN REF
- Discovery of potent, highly selective, and orally bioavailable factor XIa inhibitors for anticoagulant therapyPublication Name:European Journal of Medicinal ChemistryPublication Date:2025-05-05PMID:40010270DOI:10.1016/j.ejmech.2025.117436
- Discovery of potent and selective factor XIa inhibitors incorporating triazole-based benzoic acid as novel P2’ fragments: Molecular dynamics simulations and anticoagulant activityPublication Name:European Journal of Medicinal ChemistryPublication Date:2025-01-15PMID:39580913DOI:10.1016/j.ejmech.2024.117067
- Design, synthesis and biological evaluation of 6-chloro-quinolin-2-one derivatives as novel FXIa inhibitorsPublication Name:Bioorganic & Medicinal Chemistry LettersPublication Date:2024-02-01PMID:38211702DOI:10.1016/j.bmcl.2024.129610
- Design and Preclinical Characterization Program toward Asundexian (BAY 2433334), an Oral Factor XIa Inhibitor for the Prevention and Treatment of Thromboembolic DisordersPublication Name:Journal of Medicinal ChemistryPublication Date:2023-09-05PMCID:PMC10510402PMID:37669040DOI:10.1021/acs.jmedchem.3c00795
- Factor XIa Inhibitors in Anticoagulation Therapy: Recent Advances and PerspectivesPublication Name:Journal of Medicinal ChemistryPublication Date:2023-04-10PMID:37037122DOI:10.1021/acs.jmedchem.2c02130
Pat
- Process for the preparation of monoazo dyesPublication Number:DE-522201-CPriority Date:1928-05-15Grant Date:1931-04-01, Publication Number:BE-638782-A, Publication Number:BE-625897-A, Publication Number:BE-499305-A
- Synthesis of 13-alkyl-gon-4-onesPublication Number:US-3959322-APriority Date:1960-09-22Grant Date:1976-05-25
- Self-supporting explosives mixture that can be deformed into foils and other structuresPublication Number:DE-1124412-BPriority Date:1960-08-17
- Process for the production of chemical compoundsPublication Number:DE-1445151-A1Priority Date:1959-09-25
- Polyepoxide diphenolic acid amide compositions and said compositions modified with aldehyde condensatesPublication Number:US-2907740-APriority Date:1958-10-14Grant Date:1959-10-06
- Process for the production of alcoholsPublication Number:DE-933864-C
References
- Heitmeier, Stefan; Visser, Mayken; Tersteegen, Adrian; Dietze-Torres, Julia; Glunz, Julia; Gerdes, Christoph; Laux, Volker; Stampfuss, Jan; Roehrig, Susanne (June 2022). “Pharmacological profile of asundexian, a novel, orally bioavailable inhibitor of factor XIa”. Journal of Thrombosis and Haemostasis. 20 (6): 1400–1411. doi:10.1111/jth.15700. PMC 9313898. PMID 35289054.
- Roehrig, Susanne; Ackerstaff, Jens; Jiménez Núñez, Eloísa; Teller, Henrik; Ellerbrock, Pascal; Meier, Katharina; Heitmeier, Stefan; Tersteegen, Adrian; Stampfuss, Jan; Lang, Dieter; Schlemmer, Karl-Heinz; Schaefer, Martina; Gericke, Kersten M.; Kinzel, Tom; Meibom, Daniel (2023-09-05). “Design and Preclinical Characterization Program toward Asundexian (BAY 2433334), an Oral Factor XIa Inhibitor for the Prevention and Treatment of Thromboembolic Disorders”. Journal of Medicinal Chemistry. 66 (17): 12203–12224. doi:10.1021/acs.jmedchem.3c00795. ISSN 0022-2623. PMC 10510402. PMID 37669040.
- “Bayer initiates landmark Phase III study program to investigate oral FXIa inhibitor asundexian”. Bayer (Press release). 2022-08-28. Retrieved 2023-12-27.
- “AntiCoagulation via Inhibition of FXIa by the Oral Compound BAY 2433334 – Non-cardioembolic Stroke”. American College of Cardiology. Retrieved 2023-12-26.
- Rao, Sunil V.; Kirsch, Bodo; Bhatt, Deepak L.; Budaj, Andrzej; Coppolecchia, Rosa; Eikelboom, John; James, Stefan K.; Jones, W. Schuyler; Merkely, Bela; Keller, Lars; Hermanides, Renicus S.; Campo, Gianluca; Ferreiro, José Luis; Shibasaki, Taro; Mundl, Hardi (2022-10-18). “A Multicenter, Phase 2, Randomized, Placebo-Controlled, Double-Blind, Parallel-Group, Dose-Finding Trial of the Oral Factor XIa Inhibitor Asundexian to Prevent Adverse Cardiovascular Outcomes After Acute Myocardial Infarction”. Circulation. 146 (16): 1196–1206. doi:10.1161/CIRCULATIONAHA.122.061612. hdl:11392/2520330. ISSN 0009-7322. PMID 36030390.
- “The Next Wave of Anticoagulation: Results of PACIFIC-AF and the Future Role of Factor XIa Inhibition in Atrial Fibrillation”. American College of Cardiology. Retrieved 2023-12-26.
- “OCEANIC-AF study stopped early due to lack of efficacy”. Bayer (Press release). 2023-11-19. Retrieved 2023-12-27.
- Piccini, Jonathan P.; Patel, Manesh R.; Steffel, Jan; Ferdinand, Keith; Van Gelder, Isabelle C.; Russo, Andrea M.; Ma, Chang-Sheng; Goodman, Shaun G.; Oldgren, Jonas; Hammett, Christopher; Lopes, Renato D.; Akao, Masaharu; De Caterina, Raffaele; Kirchhof, Paulus; Gorog, Diana A.; Hemels, Martin; Rienstra, Michiel; Jones, W. Schuyler; Harrington, Josephine; Lip, Gregory Y.H.; Ellis, Stephen J.; Rockhold, Frank W.; Neumann, Christoph; Alexander, John H.; Viethen, Thomas; Hung, James; Coppolecchia, Rosa; Mundl, Hardi; Caso, Valeria (2025). “Asundexian versus Apixaban in Patients with Atrial Fibrillation”. New England Journal of Medicine. 392 (1): 23–32. doi:10.1056/NEJMoa2407105. hdl:2066/315752. PMID 39225267.
- “Ictus ischemico, i risultati della ricerca su un nuovo farmaco sperimentale: recidive ridotte del 26%”. Ospedale Maggiore di Bologna (in Italian).
- “Bayer’s asundexian demonstrated a substantial 26% reduction in stroke after a non-cardioembolic ischemic stroke or high-risk transient ischemic attack, with no increase in ISTH major bleeding versus placebo”. Bayer.
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 | |
| Clinical data | |
|---|---|
| Trade names | Sunharbo |
| Other names | BAY-2433334; BAY2433334 |
| Legal status | |
| Legal status | US: ℞-only |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2064121-65-7 |
| PubChem CID | 135206011 |
| ChemSpider | 115009501 |
| UNII | LA585UM8DE |
| KEGG | D12838 |
| Chemical and physical data | |
| Formula | C26H21ClF4N6O4 |
| Molar mass | 592.94 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
//////////Asundexian, anax labs,, APPROVALS 2026, FDA 2026, Sunharbo, LA585UM8DE, BAY2433334, BAY 2433334
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Bepirovirsen
Bepirovirsen
CAS 1403787-62-1
NA SALT 1403787-62-1
| Formula | C230H309N88O115P19S19 |
|---|---|
| Molar mass | 7344.14 g·mol−1 |
FDA 2026, APPROVALS 2026, Hibsago, hepatitis B
To treat chronic hepatitis B virus infection in certain adults without cirrhosis, in combination with existing antiviral therapy
Bepirovirsen (sold as Hibsago) is a first-in-class antisense oligonucleotide injection developed by GSK and Ionis Pharmaceuticals to treat chronic hepatitis B (CHB). It acts as a potential functional cure by targeting viral RNA, reducing surface antigen levels, and stimulating the immune system.
What It Does & How It Works
- Mechanism of Action: A non-GalNAc-conjugated antisense oligonucleotide that recognizes and destroys hepatitis B virus RNA, lowers viral protein production, and activates immune responses.
- Functional Cure Definition: Achieves sustained HBV DNA suppression and undetectable hepatitis B surface antigen (HBsAg) for at least 24 weeks after stopping all treatments.
- Clinical Trial Results: In the Phase 3 B-Well 1 and B-Well 2 trials, 19% to 24% of eligible patients achieved a functional cure and safely discontinued existing antiviral medications.
Regulatory Status & Approvals
- United States: Approved by the FDA in October 2026 for use in certain adults without cirrhosis who have been on antiviral therapy for at least six months and have HBsAg levels of 3,000 IU/mL or less. It features a boxed warning for potential serious liver reactions and low platelet counts.
- Japan: Approved as the first functional cure option for chronic hepatitis B under the brand name Hibsago.
- Other Designations: Granted Breakthrough Therapy and Priority Review designations in China and SENKU designation in Japan.
Bepirovirsen, sold under the brand name Hibsago, is an antisense oligonucleotide gapmer developed to treat hepatitis B infection.[1]
PAT
WO2012145697
PAT
WO2024214041A1
https://patents.google.com/patent/WO2024214041A1/en
Bepirovirsen is an ASO currently in clinical evaluation for treating Chronic HBV infections. It is compound ISIS No. 505358 as disclosed in WO2012/145697. Bepirovirsen has 20 linked nucleosides and has a nucleobase sequence of 5′-GCAGAGGTGAAGCGAAGTGC- 3′ (SEQ ID NO: 1), and it includes: a gap segment consisting of ten linked deoxynucleosides, a 5′ wing segment consisting of 5 linked nucleosides, and a 3′ wing segment consisting of 5 linked nucleosides, wherein the gap segment is positioned between the 5′ wing segment and the 3′ wing segment, wherein each nucleoside of each wing segment includes a 2′-O-methoxyethyl sugar, wherein each intemucleoside linkage is a phosphorothioate linkage, and wherein each cytosine is a 5 -methylcytosine. The CAS Registry Number of bepirovirsen is 1403787-62-1.
AHB-137 is an unconjugated ASO that is believed to have the same nucleobase sequence as bepirovirsen. AHB-137 is developed by Ausper Biopharma Co., Ltd. and is currently investigated in clinical studies for treating HBV infections. See WO2023/131098; Qiu, X. et al., “AHB-137, a novel and potent hepatitis B virus antisense oligonucleotide with a favorable preclinical pharmacokinetics and safety profile,” EASL 2023, Abstract No. SAT-178 (concluding that “the novel HBV ASO AHB-137 has demonstrated a favorable preclinical pharmacokinetics and safety profile”); Wu, X. et al., “AHB-137, a novel hepatitis B virus antisense oligonucleotide with substantially enhanced in vitro and in vivo antiviral activity,” EASL 2023, Abstract No. SAT-173 (concluding that “AHB-137 has more potent activity in reducing serum HBsAg than BPV [bepirovirsen] across multiple in vitro and in vivo HBV models, by reducing intrahepatic HBV RNA and HBsAg”).
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References
Mak, Lung-Yi; Hui, Rex Wan-Hin; Fung, James; Seto, Wai-Kay; Yuen, Man-Fung (2 November 2023). “Bepirovirsen (GSK3228836) in chronic hepatitis B infection: an evaluation of phase II progress”. Expert Opinion on Investigational Drugs. 32 (11): 971–983. doi:10.1080/13543784.2023.2277389. PMID 37902953. S2CID 264672407.
 | |
| Clinical data | |
|---|---|
| Trade names | Hibsago |
| Other names | GSK3228836 |
| Identifiers | |
| IUPAC name | |
| CAS Number | 1403787-62-1 |
| UNII | Z87O6SM01N |
| ChEMBL | ChEMBL4650468 |
| Chemical and physical data | |
| Formula | C230H309N88O115P19S19 |
| Molar mass | 7344.14 g·mol−1 |
| SMILES | |
| InChI | |
///////////////bepirovirsen, anax labs, FDA 2026, APPROVALS 2026, Hibsago, hepatitis B
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Tiratricol
Tiratricol
CAS 51-24-1, 1477-04-9 (hydrochloride salt)
MFC14H9I3O4 MW621.93 g/mol
9/28/2026, Emcitate, FDA 2026, APPROVALS 2026, Triac
2-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
- 3,3′,5-TRIIODOTHYROACETIC ACID
- Triiodothyroacetic acid
To treat peripheral thyrotoxicosis in patients with MCT8 deficiency
Tiratricol is a monocarboxylic acid that is (4-hydroxy-3,5-diiodophenyl)acetic acid in which the phenolic hydroxy group has been replaced by a 4-hydroxy-3-iodophenoxy group. It is a thyroid hormone analogue that has been used in the treatment of thyroid hormone resistance syndrome. It has a role as an antiviral agent, a nutraceutical, a thyroid hormone, an anti-obesity agent, an EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor and a human metabolite. It is a monocarboxylic acid, a member of phenols, an aromatic ether and an organoiodine compound
Tiratricol (also known as TRIAC or triiodothyroacetic acid), sold under the brand name Emcitate, is a thyroid hormone analogue. Triiodothyroacetic acid is also a physiologic thyroid hormone that is present in the normal organism in low concentrations. Tiratricol is an analogue of a naturally circulating metabolite of the active thyroid hormone T3.[1] MCT8 is a specific thyroid hormone transporter.[1] While T3 and T4 thyroid hormones rely on MCT8 to enter several tissues such as the brain, tiratricol can enter cells independently of MCT8.[1] Once inside cells, tiratricol activates the thyroid hormone receptor in a similar way to endogenous T3.[1]
The most common side effects are excessive sweating, irritability, anxiety and nightmares.[1]
Medical uses
Tiratricol is indicated in the management of thyroid hormone resistance syndrome.[3]
In the United States, Tiratricol is indicated for the treatment of peripheral thyrotoxicosis in adults and pediatric patients with MCT8 deficiency (Allan–Herndon–Dudley syndrome).[4][5]
Society and culture
Legal status
Tiratricol is not approved for sale in Canada. It was once an approved medication in Brazil, but its marketing authorization was suspended in 2003, effectively prohibiting its sale.[6] Tiratricol is available in France for therapy of thyroid hormone resistance and adjuvant therapy of thyroid cancer.[7]
In December 2024, the Committee for Medicinal Products for Human Use of the European Medicines Agency adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Emcitate, intended for the treatment of MCT8 deficiency (Allan-Herndon-Dudley syndrome).[1][8] The applicant for this medicinal product is Rare Thyroid Therapeutics International AB.[1] Emcitate is a hybrid medicine of Téatrois, which has been authorized in France.[1] Emcitate contains the same active substance as Téatrois but has a different indication.[1] Tiratricol was authorized for medical use in the European Union in February 2025.[1][2] Tiratricol was approved for medical use in the United States kn September 2026.[5]
Research
Tiratricol has been investigated for use in reducing goiter.[9]
It has also shown some effectiveness in reducing the atrophy caused when using corticosteroids.[10]
Tiratricol has also been widely marketed, under various trade names, as a weight loss aid. In 1999 and 2000, the United States Food and Drug Administration and Health Canada both issued warnings to the public regarding the use of dietary supplements containing tiratricol.[11][12]
LIT
C. E. Wilkinson (Biochem. J. 63, 601, 1956): The primary landmark study describing the controlled iodination approach to yield triiodothyroacetic acid.
Meltzer et al. (J. Org. Chem. 26, 1418, 1961): Advanced methods for the synthesis and purification of thyroacetic acid derivatives.
PAT
British Patent GB 803149 (1958)
https://patentscope.wipo.int/search/en/detail.jsf?docId=GB134699786&_cid=P10-MUQCJP-66503-1
EXAMPLE 1 3:5:31 – triiodo – 4 – (41 – hydroxyphenoxy)
phenyl acetic acid (Triac)
An aqueous solution of iodine (N: 40 mls.) was added dropwise with stirring during hour to a solution of 3:5-diiodo-4-(41hydroxyphenoxy)phenyl acetic acid (Diac) (9.92 g.; 0.02 mol.) in aqueous ethylamine (33%: 120 mls.). After a further hour the solution was acidified with hydrochloric acid (5N) at 10-15 (ice-bath cooling). The precipitate, which became gummy on filtration, was triturated with water containing a few drops of hydrochloric acid and again filtered.
The solid was then ground with water containing a little hydrochloric acid, filtered, washed with water and dried over phosphorus pentoxide (12.10 g.; m.p. 161-72 ). The crude product was dissolved in methanol (240 mls.) and stirred during the dropwise addition of water (180 mls.). After standing overnight, the mixture was decanted from the tarry material which had separated. Water (60 mls.) was added in one portion, and the milky solution allowed to stand several hours until crystallisation was complete. The product was collected and dried over phosphorus pentoxide, 7.1 g. (63%) m.p. 181-3 (after sinteringg at about 60 , effervescing at 100 and resolidifying at about 115 ). A sample from a previous experiment was dried by heating slowly to 100 in high vacuum over phosphorus pentoxide. Found: C, 27.3; H, 1.5; I, 61.2, C14H9O4I3 requires C, 27.0; H, 1.5; I, 61.2%.
To prepare the sodium salt of Triac 42.8 g. of Triac was dissolved in a hot solution of sodium carbonate (7.3 g.) in water (420 mis.) and filtered. A solution of salt (35%; 42 mis.) was added and the mixture cooled, finally in the refrigerator. The product was collected and dried to constant weight over phosphorus pentoxide (34.1 g.).
PAT
British Patent GB 805761 (1958)
PAT
US Patent US8071134B2
https://patentscope.wipo.int/search/en/detail.jsf?docId=US42563548&_cid=P10-MUQCHB-64862-1
PAT
Chinese Patent CN113181152B
https://patentscope.wipo.int/search/en/detail.jsf?docId=CN333439736&_cid=P10-MUQCEZ-62879-1
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References
- “Emcitate EPAR”. European Medicines Agency (EMA). 12 December 2024. Retrieved 16 December 2024. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
- “Emcitate PI”. Union Register of medicinal products. 17 February 2025. Retrieved 27 February 2025.
- Carvalho GA, Ramos HE (2004). “[Thyroid hormone resistance syndrome]” (PDF). Arq Bras Endocrinol Metabol (in Portuguese). 48 (1): 83–92. doi:10.1590/S0004-27302004000100010. PMID 15611821.
- “EMCITATE — Now Approved”. EMCITATE® — Now Approved. Retrieved 29 September 2026.
- “Egetis Therapeutics Announces U.S. FDA Approval of EMCITATE® (tiratricol) for Patients with MCT8 Deficiency”. Egetis Therapeutics. Retrieved 29 September 2026.
- “Anvisa suspende Tiratricol” (in Portuguese). Brazilian Society of Endocrinology and Metabolism. Archived from the original on 9 October 2007. Retrieved 8 August 2007.
- Laboratoires DB PHARMA: Teatrois Deprecated link archived 2015-01-19 at archive.today information
- “First treatment for peripheral thyrotoxicosis in patients with Allan-Herndon-Dudley syndrome”. European Medicines Agency (EMA) (Press release). 13 December 2024. Retrieved 16 December 2024.
- Brenta G, Schnitman M, Fretes O, et al. (November 2003). “Comparative efficacy and side effects of the treatment of euthyroid goiter with levo-thyroxine or triiodothyroacetic acid”. J. Clin. Endocrinol. Metab. 88 (11): 5287–92. doi:10.1210/jc.2003-030095. PMID 14602763.
- Yazdanparast P, Carlsson B, Oikarinen A, Risteli J, Lavin T, Faergemann J (November 2006). “Action of topical thyroid hormone analogue, triiodothyroacetic acid in reversing glucocorticoid-induced skin atrophy in humans”. Thyroid. 16 (11): 1157–62. doi:10.1089/thy.2006.16.1157. PMID 17123343.
- “FDA Warns Against Consuming Dietary Supplements Containing Tiratricol” (Press release). U.S. Food and Drug Administration. 21 November 2000. Archived from the original on 22 January 2001. Retrieved 8 August 2007.
- “Health Canada issues warning on products containing Tiratricol (TRIAC)” (Press release). Health Canada. 2 December 1999. Retrieved 8 August 2007.
 | |
 | |
| Clinical data | |
|---|---|
| Trade names | Emcitate |
| Other names | 3,3′,5-triiodothyroacetic acid TRIAC |
| AHFS/Drugs.com | International Drug Names |
| Drug class | Thyroid hormone |
| ATC code | H03AA04 (WHO) D11AX08 (WHO) |
| Legal status | |
| Legal status | EU: Rx-only[1][2] |
| Pharmacokinetic data | |
| Metabolism | Liver glucuronidation |
| Excretion | Bile duct |
| Identifiers | |
| IUPAC name | |
| CAS Number | 51-24-1  |
| PubChem CID | 5803 |
| IUPHAR/BPS | 2637 |
| DrugBank | DB03604  |
| ChemSpider | 5598 |
| UNII | 29OQ9EU4R1 |
| KEGG | D07214 |
| ChEBI | CHEBI:40021 |
| ChEMBL | ChEMBL41632 |
| CompTox Dashboard (EPA) | DTXSID2045232  |
| ECHA InfoCard | 100.000.079 |
| Chemical and physical data | |
| Formula | C14H9I3O4 |
| Molar mass | 621.935 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
//////////////tiratricol, anax labs, Emcitate, FDA 2026, APPROVALS 2026, Triac
#tiratricol, #anax labs, #Emcitate, #FDA 2026, #APPROVALS 2026, #Triac
Zilurgisertib
Zilurgisertib
CAS 2173389-57-4
MW 502.6 g/mol MFC30H38N4O3
Atebrioz, FDA 2026, APPROVALS 2026, L5Z9S25HO2, INCB 000928
2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1R,5S)-3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide
To reduce the volume of total new heterotopic ossification in adults and pediatric patients 12 years and older with fibrodysplasia ossificans progressiva
Zilurgisertib is an inhibitor of activin A receptor type 1 (activin receptor-like kinase 2; ALK2; ALK-2; ACVR1; ACTR-I), with potential anti-anemic and ossification suppressive activities. Upon administration, zilurgisertib targets, binds to and inhibits the activity of ALK-2. This prevents ALK2-mediated signaling and ALK2-mediated excessive bone morphogenetic protein (BMP) signaling. This may suppress heterotopic ossification (HO). As ALK-2 enhances the secretion of hepcidin, a peptide liver hormone and a key modulator of iron homeostasis, zilurgisertib is able to decrease hepcidin expression in the liver, thereby increasing and restoring plasma iron levels, enhancing erythropoiesis, and correcting anemia of chronic disease (ACD). ALK2, a serine/threonine receptor kinase and type I cell surface receptor for BMPs, is constitutively activated due to activating mutations in inflammatory conditions, various types of cancer, and in fibrodysplasia ossificans progressiva (FOP). Elevated serum hepcidin levels enhance storage of iron, reduce iron availability and causes iron deficiency anemia.
Zilurgisertib, sold under the brand name Atebrioz, is a medication used for the treatment of fibrodysplasia ossificans progressiva.[1] It is an selective activin receptor-like kinase-2 (ALK2) inhibitor.[1][2]
Zilurgisertib was approved for medical use in the United States in September of 2026.[3]
Medical uses
Zilurgisertib is indicated to reduce the volume of total new heterotopic ossification (abrnomal bone formation) in people aged twelve years of age and older with fibrodysplasia ossificans progressiva.[1]
Fibrodysplasia ossificans progressiva is a rare genetic disease caused certain mutations in the ACVR1/ALK2 gene which controls new bone growth.[3] As a result, connective tissues such as muscle, tendons, and ligaments gradually turn into bone, causing limited movement, deformities, severe disability, and early death.[3]
Adverse effects
Zilurgisertib can cause fetal harm based on data from animal studies.[3]
The most common side effects include headache, joint pain, upper respiratory tract infection, nosebleeds, and nausea.[3]
History
The effectiveness of zilurgisertib was evaluated in a randomized, double-blind, placebo‑controlled trial (NCT05090891) in which 63 participants with FOP were randomly assigned to receive zilurgisertib 100 mg or placebo once daily for 24 weeks followed by a 292-week, single-arm, open-label extension period during which participants received oral zilurgisertib 100 mg daily.[3]
Society and culture
Legal status
Zilurgisertib was approved for medical use in the United States in September 2026.[4] The US Food and Drug Administration granted the application for zilurgisertib fast track, priority review, and orphan drug designations for this indication.[3]
Names
Zilurgisertib is the international nonproprietary name.[5]
Zilurgisertib is sold under the brand name Atebrioz.[3]
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US242623881&_cid=P22-MUNHEN-48106-1
Example 34: 2-amino-N-(4-hydroxybicyclo[2.2.2]octan-1-yl)-5-(4-((1R,5S)-3-(tetrahydro-2H-pyran-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl)phenyl)nicotinamide (also named compound A herein)
| To a solution of 2-amino-5-(4-((1R,5S)-3-(tetrahydro-2H-pyran-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl)phenyl)nicotinic acid TFA salt (Intermediate 14a, 4.10 g, 8.14 mmol) and 4-aminobicyclo[2.2.2]octan-1-ol hydrochloride (2.17 g, 12.2 mmol) in anhydrous DMF (60 mL) was added N-methylmorpholine (2.24 mL, 20.4 mmol) and HATU (4.64 g, 12.2 mmol) under a nitrogen atmosphere at RT. The reaction mixture was stirred for 2 h and then diluted with a sat. aq. solution of NaHCO 3 and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over MgSO 4, filtered and concentrated under reduced pressure. The crude product was purified by reversed-phase chromatography (Method 3b). Pure fractions were treated with a sat. aq. NaHCO 3 solution and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over MgSO 4, filtered and concentrated under reduced pressure to give the title compound as an off-white solid. The absolute configuration as depicted was confirmed by X-ray crystallography of the title compound in a complex with the ALK-2 kinase domain. 1H NMR (400 MHz, DMSO-d6) δ 8.34 (d, 1H), 7.98 (d, 1H), 7.79 (s, 1H), 7.57 (d, 2H), 7.23 (d, 2H), 6.92 (s, 2H), 4.31 (s, 1H), 3.91-3.78 (m, 2H), 3.40 (bs, 1H), 3.33-3.24 (m, 2H), 3.11 (d, 1H), 2.57 (bs, 1H), 2.50-2.34 (m, 1H), 2.34 (bs, 1H), 2.12-1.94 (m, 6H), 1.90-1.72 (m, 3H), 1.71-1.51 (m, 6H), 1.51-1.34 (m, 2H), 1.31 (t, 1H), 0.82-0.68 (m, 1H). (UPLC-MS) t R 0.54 min; ESI-MS 503 [M+H] +. Chiral HPLC (ChiralPak Id, 5 μm, flow rate: 1 mL/min, detection wavelength: 270 nm, mobile phase: heptane:isopropanol 60:40 (+0.1% diethylamine)): t R 18.7 min, 92.3% ee. |
| 13C NMR (DMSO-d6) δ: 167.80, 157.69, 148.28, 141.27, 134.91, 134.79, 126.40, 125.66, 123.53, 111.01, 66.22, 65.59, 59.10, 55.46, 52.04, 33.72, 31.92, 31.77, 30.59, 29.61, 24.14, 17.20. |
| 13C NMR (DMSO-d6) δ: 167.2, 155.8, 144.3, 142.0, 139.6, 133.8, 127.7, 126.3, 124.1, 110.0, 65.8, 62.5, 55.7, 53.2, 29.9, 28.8, 28.7, 23.5, 16.6. |
| The starting material, 2-Amino-5-(4-((1R,5S)-3-(tetrahydro-2H-pyran-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl)phenyl)nicotinate dihydrochloride, was obtained as follows: |
| 13C NMR (DMSO-d6) δ: 165.0, 154.0, 143.5, 142.0, 140.1, 132.8, 127.7, 126.5, 124.2, 110.7, 65.8, 62.5, 55.6, 53.3, 53.3, 29.9, 28.9, 28.8, 23.6, 16.8. |
| The starting material, 1R,5S)-1-(4-bromophenyl)-3-(tetrahydro-2H-pyran-4-yl)-3-azabicyclo[3.1.0]hexan-3-ium chloride, was obtained as follows: |
| 13C NMR (DMSO-d6) δ: 138.3, 131.9, 129.2, 120.4, 65.5, 62.3, 56.2, 53.9, 29.1, 28.9, 24.8, 23.0. MS(ESI-TOF): 322.0761 [M+H]+ |
The complete way of manufacture of Alternative Example 34 A is depicted in the following Reaction Scheme 34A:
| The first compound in this scheme, A1, can be obtained as follows: |
PAT
PAT
PAT
PAPERS
- Discovery and Characterization of Zilurgisertib, a Potent and Selective Inhibitor of Activin Receptor-like Kinase-2 (ALK2) for the Treatment of Fibrodysplasia Ossificans ProgressivaPublication Name:ACS Medicinal Chemistry LettersPublication Date:2025-10-31PMCID:PMC12621050PMID:41256990DOI:10.1021/acsmedchemlett.5c00516
- Pharmacokinetics of Zilurgisertib With and Without Food from Single and Multiple Ascending Dose Phase 1 Studies in Healthy AdultsPublication Name:European Journal of Drug Metabolism and PharmacokineticsPublication Date:2024-12-09PMCID:PMC11802711PMID:39652202DOI:10.1007/s13318-024-00926-z
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References
- “Atebrioz FDA label” (PDF). files.mirumpharma.com.
- Gangat N, Tefferi A (June 2025). “Emerging Pathogenetic Mechanisms and New Drugs for Anemia in Myelofibrosis and Myelodysplastic Syndromes”. American Journal of Hematology. 100 Suppl 4: 51–65. doi:10.1002/ajh.27659. PMID 40056069.
- Center for Drug Evaluation and Research (25 September 2026). “FDA Approves Third Treatment for Fibrodysplasia Ossificans Progressiva”. U.S. Food and Drug Administration. U.S. Food and Drug Administration (FDA). Retrieved 27 September 2026.
This article incorporates text from this source, which is in the public domain. - “Mirum Pharmaceuticals and Incyte Announce U.S. FDA Approval of Atebrioz (zilurgisertib) for Adult and Pediatric Patients with Fibrodysplasia Ossificans Progressiva” (Press release). Mirum Pharmaceuticals. 25 September 2026. Retrieved 27 September 2026 – via Business Wire.
- World Health Organization (2022). “International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 88”. WHO Drug Information. 36 (3). hdl:10665/363551.
External links
- “Zilurgisertib ( Code – C175551 )”. EVS Explore.
- “Zilurgisertib Fumarate ( Code – C199021 )”. EVS Explore.
- Clinical trial number NCT05090891 for “To Assess the Efficacy, Safety, and Tolerability of INCB000928 in Participants With Fibrodysplasia Ossificans Progressiva (Progress)” at ClinicalTrials.gov
 | |
| Clinical data | |
|---|---|
| Trade names | Atebrioz |
| Other names | INCB-000928, INCB000928 |
| License data | US DailyMed: Zilurgisertib |
| Routes of administration | By mouth |
| Drug class | Kinase inhibitor (ALK2 selective) |
| ATC code | None |
| Legal status | |
| Legal status | US: ℞-only[1] |
| Identifiers | |
| CAS Number | 2173389-57-42173390-29-7 |
| PubChem CID | 138628908162623634 |
| IUPHAR/BPS | 11888 |
| UNII | L5Z9S25HO21R349830SB |
| KEGG | D12547D12548 |
| ChEMBL | ChEMBL5314579 |
| Chemical and physical data | |
| Formula | C30H38N4O3 |
| Molar mass | 502.659 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
///////////zilurgisertib, anax labs, Atebrioz, FDA 2026, APPROVALS 2026, L5Z9S25HO2, INCB 000928
#zilurgisertib, #anax labs, #Atebrioz, #FDA 2026, #APPROVALS 2026, #L5Z9S25HO2, #INCB 000928
Tavapadon
Tavapadon
- CAS No.:1643489-24-0
- Formula:C19H16F3N3O3
- Molecular Weight:391.34
9/25/2026, Juvmo, FDA 2026, APPROVALS 2026, CEREVEL, CVL 751, PF 6649751, PF-06649751,
To treat Parkinson’s disease in adults
Tavapadon (PF-06649751) is an orally active and highly selective dopamine D1/D5 receptor partial agonist. Tavapadon is effective in enabling movement and reducing disability and has the potential for Parkinson’s disease.
Tavapadon (developmental code names CVL-751, PF-06649751) is a dopamine receptor agonist which is under development for the treatment of Parkinson’s disease.[2][3][4] It is under development by Cerevel Therapeutics, which acquired tavapadon from Pfizer in 2018.[2] It is taken by mouth.[1]
Tavapadon acts as a highly selective partial agonist of the dopamine D1 receptor (Ki = 9 nM; IATooltip Intrinsic activity = 65%) and the dopamine D5 receptor (Ki = 13 nM; IA = 81%).[3][4][1] It has no significant affinity or functional activity at the D2-like receptors (D2, D3, D4) (Ki ≥ 4,870 to 6,720 nM).[1] Tavapadon also shows biased agonism for Gs-coupled signaling at the D1-like receptors.[1][3]
As of December 2024, tavapadon has completed phase 3 clinical trials for Parkinson’s disease.[2]
- OriginatorPfizer
- DeveloperCerevel Therapeutics; Pfizer
- ClassAntiparkinsonians; Small molecules
- Mechanism of ActionDopamine D1 receptor agonists; Dopamine D5 receptor agonists
- registrationParkinson’s disease
- 01 Dec 2025Cerevel Therapeutics completes a phase III TEMPO-4 trial in Parkinson Disease (In adults, In elderly in the US, Australia, Bulgaria, Canada, Czechia, France, Germany, Hungary, Israel, Italy, Poland, Serbia, Spain, and Ukraine (PO) (NCT04760769)
- 28 Nov 2025No recent reports of development identified for phase-I development in Parkinson’s-disease(In volunteers) in USA (PO, Tablet)
- 26 Sep 2025Preregistration for Parkinson’s disease (Early-stage disease, In the elderly, In adults) in USA (PO)
The industrial synthesis of tavapadon typically proceeds via a convergent sequence:
- Ether Formation: Coupling of a substituted phenol derivative (such as a 4-hydroxy-2-methylphenyl component) with a 2-halogenated-3-(trifluoromethyl)pyridine (e.g., 2-chloro-3-trifluoromethylpyridine) via nucleophilic aromatic substitution ($S_NAr$) or transition-metal-catalyzed cross-coupling to construct the biaryl ether framework.
- Pyrimidine Ring Construction / Functionalization: Assembly or modification of the 1,5-dimethylpyrimidine-2,4-dione core onto the substituted aryl backbone, often utilizing base-catalyzed cyclizations (e.g., using methylating agents and urea/amide derivatives).
- Chiral Resolution / Final Purification: Final isolation of the target enantiomer or specific crystalline form (as outlined in WO2023102087A1 and WO2023143321) to meet active pharmaceutical ingredient (API) regulatory grades.
PAT
W02014207601
Examples 7 and 8
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2014207601&_cid=P12-MUKNR1-83868-1
Step 1. Synthesis of tert-butyl 4-bromo-3,5-dimethyl-2,6-dioxo-3,6-dihydropyrimidine-1(2H)-carboxylate (C22).
Compound C2 (800 mg, 3.65 mmol), di-tert-butyl dicarbonate (99%, 966 mg, 4.38 mmol), triethylamine (0.62 mL, 4.4 mmol) and 4-(dimethylamino)pyridine (45 mg, 0.36 mmol) were combined in tetrahydrofuran (15 mL) and heated to 70 °C for 1 hour, then allowed to stir at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, and the residue was purified via chromatography on silica gel (Gradient: 10% to 25% ethyl acetate in heptane) to provide the product as a white solid. Yield: 1.10 g, 3.45 mmol, 94%. 1H NMR (400 MHz, CDCl3) δ 3.64 (s, 3H), 2.12 (s, 3H), 1.61 (s, 9H).
Step 2. Synthesis of ten-butyl 4-[4-(benzyloxy)-2-methylphenyl]-3,5-dimethyl-2,6-dioxo-3,6-dihydropyrimidine-1(2H)-carboxylate ( C23).
A mixture of C22 (1.00 g, 3.13 mmol), [4-(benzyloxy)-2-methylphenyl]boronic acid (98%, 1.16 g, 4.68 mmol), chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) – tert-butyl methyl ether adduct (S-Phos precatalyst) (119 mg, 0.156 mmol), and cesium carbonate (3.06 g, 9.39 mmol) in 2-methyltetrahydrofuran (10 mL) and water (3 mL) was heated at 50 °C for 66 hours. The reaction mixture was diluted with water and ethyl acetate, and then filtered to remove suspended solids. The filtrate was extracted several times with ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was suspended in a 1:3 mixture of ethyl acetate and heptane, stirred for several minutes, and filtered, providing the product as a white solid. Yield: 970 mg, 2.22 mmol, 71%. LCMS m/z 337.2 [(M-Boc)+H]+. 1H NMR (400 MHz, CDCl3) δ 7.34-7.48 (m, 5H), 6.91-7.01 (m, 3H), 5.10 (s, 2H), 3.01 (s, 3H), 2.16 (br s, 3H), 1.66 (s, 9H), 1.64 (s, 3H).
Step 3. Synthesis of 6-(4-hydroxy-2-methylphenyl)-1,5-dimethylpyrimidine-2,4(1H,3H)-dione (C24).
Racemate C25 (1.30 g, 3.32 mmol) was separated into its atropenantiomers via chiral chromatography (Column: Phenomenex Lux Cellulose-2; Gradient: heptane / ethanol). The first-eluting atropenantiomer, obtained as a tan solid that exhibited a negative (-) rotation, was designated as Example 7. Yield: 536 mg, 1.37 mmol, 41%. The second-eluting atropenantiomer, also obtained as a tan solid but with a positive (+) rotation, was designated as Example 8. Yield: 553 mg, 1.41 mmol, 42%. 7: LCMS m/z 392.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.34 (ddq, J=4.9, 1.9, 0.6 Hz, 1H), 8.30 (br s, 1H), 8.05 (ddq, J=7.6, 1.9, 0.7 Hz, 1H), 7.13-7.21 (m, 4H), 3.06 (s, 3H), 2.21 (br s, 3H), 1.69 (s, 3H). 8: LCMS m/z 392.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.34 (br d, J=4.9 Hz, 1H), 8.30 (br s, 1H), 8.05 (br d, J=7.5 Hz, 1H), 7.13-7.22 (m, 4H), 3.06 (s, 3H), 2.21 (br s, 3H), 1.69 (s, 3H).
PAT
WO2015162084 SIMILAR
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2015162084&_cid=P12-MUKNEL-70374-1
PAT
US9334247
PAT
WO2023102087A1
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2023102087&_cid=P12-MUKNKO-77090-1
Tavapadon, 1 , 5-dimethy I -6-(2-methy 1 -4- { [3 -(tri fluoromethyl)pyri din-2-yl]oxy}phenyl)pyrimidine-2,4(lH,3H)-dione has the following chemical structure:
and is described in International Publication No. W02014/207601. As disclosed in International Publication No. W02014/207601, the class of compounds encompassing Tavapadon, may exist as conformational isomers due to hindered rotation about a single bond, i.e., atropisomerism. In the case of Tavapadon, the atropenantiomers or atropisomers may be designated as (-)-Tavapadon or (+)-Tavapadon, depending on the optical rotation, and can include any mixture thereof, including a racemic mixture, wherein the racemic mixture can be designated as (±)-Tavapadon. According to International Publication No.
W02014/207601, the compound Tavapadon may be obtained as a racemate (i.e., (±)-Tavapadon), which may be separated by chiral chromatography into two atropenantiomers. The atropisomer exhibiting an anticlockwise (negative) rotation on a polarimeter is denoted the (-)-atropenantiomer [i.e., (-)-Tavapadon], and the atropisomer exhibiting a clockwise (positive) rotation on a polarimeter is denoted the (+)-atropenantiomer [i.e., (+)-Tavapadon],
PAT
WO2023143321 (or corresponding US20250145588A1 / CN115974803A equivalents)
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References
 | |
| Clinical data | |
|---|---|
| Other names | CVL-751; PF-6649751; PF-06649751 |
| Routes of administration | By mouth[1] |
| Drug class | Dopamine receptor agonist |
| Identifiers | |
| IUPAC name | |
| CAS Number | 1643489-24-0 |
| PubChem CID | 86764100 |
| ChemSpider | 48062699 |
| UNII | PT4P8MJP8L |
| KEGG | D11431 |
| ChEMBL | ChEMBL3697617 |
| CompTox Dashboard (EPA) | DTXSID301337071 |
| Chemical and physical data | |
| Formula | C19H16F3N3O3 |
| Molar mass | 391.350 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
References
- Bezard E, Gray D, Kozak R, Leoni M, Combs C, Duvvuri S (2024). “Rationale and Development of Tavapadon, a D1/D5-Selective Partial Dopamine Agonist for the Treatment of Parkinson’s Disease”. CNS Neurol Disord Drug Targets. 23 (4): 476–487. doi:10.2174/1871527322666230331121028. PMC 10909821. PMID 36999711.
Tavapadon is a highly selective partial agonist at D1 and D5 dopamine receptors, [52] with little to no functional activity at D2, D3, or D4 receptors in vitro (unpublished data). Assays measuring the displacement of radioligand binding in cell lines expressing recombinant human dopamine receptors have shown that tavapadon has a high affinity for both D1 (Ki = 9 nM) and D5 (Ki = 13 nM) (unpublished data). Conversely, tavapadon had a low affinity at D2 (Ki ≥ 6210 nM), D3 (Ki ≥ 6720 nM), and D4 (Ki ≥ 4870 nM) (unpublished data). […] In vitro assays of functional activity have confirmed that tavapadon acts as a partial agonist by binding at D1 and D5 receptors, corresponding to 65% and 81% of dopamine’s intrinsic activity, respectively, and inducing functional receptor activation, with half-maximal effective concentration (EC50) values of 19 nM and 17 nM (unpublished data).
- “Tavapadon – Cerevel Therapeutics”. Adis Insight. Springer Nature Switzerland AG.
- Cerri S, Blandini F (December 2020). “An update on the use of non-ergot dopamine agonists for the treatment of Parkinson’s disease”. Expert Opinion on Pharmacotherapy. 21 (18): 2279–2291. doi:10.1080/14656566.2020.1805432. PMID 32804544. S2CID 221163451.
- Hall A, Provins L, Valade A (January 2019). “Novel Strategies To Activate the Dopamine D1 Receptor: Recent Advances in Orthosteric Agonism and Positive Allosteric Modulation”. Journal of Medicinal Chemistry. 62 (1): 128–140. doi:10.1021/acs.jmedchem.8b01767. PMID 30525590. S2CID 54469910.
////////tavapadon, anax labs, Juvmo, FDA 2026, APPROVALS 2026, CEREVEL, CVL 751, PF 6649751, PF-06649751,
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Lirafugratinib
Lirafugratinib
- CAS No.:2549174-42-5
- Formula:C28H24FN7O2
- Molecular Weight:509.53
FDA 2026, APPROVALS 2026, Lyrfigtu, RLY-4008, RLY 4008, 23SEPT2026
N-(4-(4-amino-5-(3-fluoro-4-((4-methylpyrimidin-2-yl)oxy)phenyl)-7-methyl-7H-pyrrolo[2,3-
d]pyrimidin-6-yl)phenyl)methacrylamide (lirafugratinib)
To adults with previously treated unresectable, locally advanced or metastatic cholangiocarcinoma harboring a fibroblast growth factor receptor 2 gene fusion or other rearrangement
Lirafugratinib (RLY-4008) is an orally active, irreversible and highly selective FGFR2 inhibitor with an IC50 of 3 nM. Lirafugratinib covalently binds to Cys491. Lirafugratinib targets FGFR2 primary alterations and resistance mutations and induces tumor regression while sparing other FGFRs.
Lirafugratinib (Lyrfigtu) received FDA approval on September 23, 2026, for adults with previously treated, unresectable or metastatic cholangiocarcinoma involving FGFR2 gene fusions or rearrangements.
Overview & Mechanism
- Drug Class: An oral, selective, and irreversible FGFR2 small-molecule inhibitor.
- Developer/Marketed By: Developed by Relay Therapeutics and commercialized globally by Elevar Therapeutics.
- How it Works: Covalently targets the FGFR2 kinase domain to inhibit tumor-driving signaling while sparing other FGFR proteins to limit off-target effects.
Efficacy
- Clinical Trial: Assessed in the phase 1/2 REFOCUS trial (NCT04526106) involving 116 previously treated, FGFR-inhibitor-naive patients.
- Key Metrics: Demonstrated an objective response rate of 46%, a median duration of response of 11.8 months, and a median progression-free survival of 11.3 months.
Dosing & Administration
- Recommended Dose: 70 mg orally once daily on a continuous basis until disease progression or unacceptable toxicity.
Safety & Warnings
- Common Adverse Events: Hand-foot syndrome, stomatitis, nail issues, and ocular/retinal toxicities.
- Special Warnings: Includes precautions for ocular toxicity, hyperphosphatemia, soft tissue mineralization, and embryo-fetal risks
PAPER
https://pmc.ncbi.nlm.nih.gov/articles/PMC10861881
SEE https://pmc.ncbi.nlm.nih.gov/articles/instance/10861881/bin/pnas.2317756121.sapp.pdf
N-(4-(4-amino-5-(3-fluoro-4-((4-methylpyrimidin-2-yl)oxy)phenyl)-7-methyl-7Hpyrrolo[2,3-d]pyrimidin-6-yl)phenyl)methacrylamide (lirafugratinib)
5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
A round bottomed flask was charged with 5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-amine (10.0 g,
47.16 mmol), Cs2CO3 (22.99 g, 70.75 mmol), DMF (120 mL) and a stirbar. Iodomethane (8.03 g,
56.59 mmol) was added, and the solution was stirred for 1 h at room temperature. The reaction mixture was diluted with H2O (300 mL), and the aqueous phase was extracted with ethyl acetate
(300 mL) three times. The combined organic layers were washed with saturated brines, dried
over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude material was
purified by HPLC. Concentration in vacuo resulted in 5-bromo-7-methyl-7H-pyrrolo[2,3-
d]pyrimidin-4-amine (5 g, 47.1 % ) as an off-white solid.
5-bromo-6-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
A round bottomed flask was charged with 5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-
amine (5 g, 22.12 mmol), DCM (50 mL) and TFA (2 mL) and a stirbar. 1-iodopyrrolidine-2,5-
dione (5.97 g, 26.54 mmol) was added, and the solution was stirred for 2 h at room temperature.
The reaction mixture was diluted with Na2SO3 solution (200 mL), and the aqueous phase was
extracted with DCM (200 mL) three times. The combined organic layers were washed with
saturated brines, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting
crude material was purified by HPLC. Concentration in vacuo resulted in 5-bromo-6-iodo-7-
methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (4 g, 51.3 %) as a yellow solid.
tert-butyl (4-(4-amino-5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl)carbamate
A resealable reaction vial was charged with 5-bromo-6-iodo-7-methyl-7H-pyrrolo[2,3-
d]pyrimidin-4-amine (4 g, 11.36 mmol), tert-butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-
yl)phenyl)carbamate (4.35 g, 13.63 mmol), Pd(dppf)Cl2 (994.16 mg, 1.36 mmol), K3PO4 (7.22
g, 34.08 mmol), DMF (50 mL), H2O (6.25 mL) and a stir bar before being evacuated and purged
with nitrogen three times. The mixture was stirred for 2 h at 90 °C. The reaction mixture was
diluted with H2O (300 mL), and the aqueous phase was extracted with ethyl acetate (300 mL)
three times. The combined organic layers were washed with brines, dried over sodium sulfate,
filtered, and concentrated in vacuo. The resulting crude material was purified by silica gel
chromatography (eluting with MeOH/DCM = 1/40). Concentration in vacuo resulted in tert-butyl
(4-(4-amino-5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl)carbamate (3 g, 63.4%)
as a yellow solid.
6-(4-aminophenyl)-5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
A round bottomed flask was charged with tert-butyl (4-(4-amino-5-bromo-7-methyl-7Hpyrrolo[2,3-d]pyrimidin-6-yl)phenyl)carbamate (3 g, 7.19 mmol), DCM (50 mL) and TFA (12.5mL) and a stirbar. The solution was stirred for 1 h at room temperature. The reaction mixture
was diluted with H2O (100 mL), and the aqueous phase was extracted with DCM (50 mL) three
times. The pH of aqueous phase was adjusted to 7~8, then the aqueous phase was extracted with
DCM (100 mL) three times. The combined organic layers were washed with saturated brines,
dried over sodium sulfate, filtered, and concentrated in vacuo resulted in 6-(4-aminophenyl)-5-
bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (2.1 g, 92.1%) as a yellow solid.
N-(4-(4-amino-5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl)methacrylamide
A resealable reaction vial was charged with 6-(4-aminophenyl)-5-bromo-7-methyl-7Hpyrrolo[2,3-d]pyrimidin-4-amine (2.1 g, 6.62 mmol), pyridine (785 mg, 9.93 mmol), DCM (100
mL) and a stir bar before being evacuated and purged with nitrogen three times. Methacryloyl
chloride (757.3 mg, 7.28 mmol) was added slowly at 0 oC. Then the mixture was stirred for 2 h
at room temperature. The reaction mixture was diluted with H2O (100 mL), and the aqueous
phase was extracted with DCM (100 mL) three times. The combined organic layers were washed
with brines, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude
material was purified by silica gel chromatography (eluting with MeOH/DCM=1/40).
Concentration in vacuo resulted in N-(4-(4-amino-5-bromo-7-methyl-7H-pyrrolo[2,3-
d]pyrimidin-6-yl)phenyl)methacrylamide (1.8 g, 70.5%) as an off-white solid.
2-(4-bromo-2-fluorophenoxy)-4-methylpyrimidine
A round bottomed flask was charged with 4-bromo-2-fluorophenol (1.0 g, 5.24 mmol), 2-fluoro4-methylpyrimidine (704 mg, 6.28 mmol), Cs2CO3 (5.12 g, 15.7 mmol) and a stirbar. DMF (20
mL) was added, and the solution was stirred for 1 h at 100 oC. The reaction mixture was diluted
with H2O (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mL) three
times. The combined organic layers were washed with saturated brines, dried over sodium
sulfate, filtered, and concentrated in vacuo. The resulting crude material was purified by HPLC.
Concentration in vacuo resulted in 2-(4-bromo-2-fluorophenoxy)-4-methylpyrimidine (1.48 g,
99.8 %) as an off-white amorphous solid.
2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-4-methylpyrimidine
A solution/mixture of 2-(4-bromo-2-fluorophenoxy)-4-methylpyrimidine (500.00 mg, 1.77
mmol), bis(pinacolato)diboron (672.75 mg, 2.65 mmol), KOAc (520 mg, 5.3 mmol) and
Pd(dppf)Cl2 (129.4 mg, 0.177 mmol) in DMF (10 mL) was stirred for 2 h at 80 oC under nitrogen
atmosphere. The resulting mixture was diluted with water and extracted with EA. The combined
organic layers were washed with brines, dried over anhydrous Na2SO4. After filtration, the
filtrate was concentrated under reduced pressure. The residue was purified by HPLC.
Concentration in vacuo resulted in 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-
yl)phenoxy)-4-methylpyrimidine (430 mg, 73.7%) as a yellow solid.
2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-4-methylpyrimidine
A resealable reaction vial was charged with N-(4-(4-amino-5-bromo-7-methyl-7H-pyrrolo[2,3-
d]pyrimidin-6-yl)phenyl)methacrylamide (100 mg, 0.259 mmol), 2-(2-fluoro-4-(4,4,5,5-
tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-4-methylpyrimidine (102.6 mg, 0.310 mmol),
Pd(DtBPF)Cl2 (16.9 mg, 0.026 mmol), CsF (118 mg, 0.776 mmol), DMF (2 mL), H2O (0.25
mL) and a stir bar before being evacuated and purged with nitrogen three times. The mixture was
stirred for 1 h at 90 °C. The reaction mixture was diluted with H2O (10 mL), and the aqueousphase was extracted with DCM (10 mL) three times. The combined organic layers were washed
with brines, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude
material was purified by Pre-HPLC (Column: XBridge Prep C18 OBD Column, 19*150 mm,
5μm; Mobile Phase A: Water(10 mmol/L NH4HCO3), Mobile Phase B: ACN; Flow rate: 25
mL/min; Gradient: 25% B to 50% B in 7 min, 50% B; Wave Length: 254/220 nm; RT1(min):
6.5). Concentration in vacuo resulted in N-(4-(4-amino-5-(3-fluoro-4-((4-methylpyrimidin-2-
yl)oxy)phenyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl)methacrylamide ( 27.2 mg,
20.6%) as an off-white solid. LC/MS(BAS1): [M+H]+= 510.20; tR =1.405 min. 1H NMR (400
MHz, DMSO-d6) δ 9.92 (s, 1H), 8.47 (d, J = 5.0 Hz, 1H), 8.21 (s, 1H), 7.79 – 7.72 (m, 2H), 7.38
– 7.28 (m, 3H), 7.22 – 7.14 (m, 2H), 7.10 (dd, J = 8.1, 2.1 Hz, 1H), 5.98 (s, 2H), 5.80 (s, 1H),
5.54 (d, J = 1.7 Hz, 1H), 3.59 (s, 3H), 2.42 (s, 3H), 1.95 (d, J = 1.2 Hz, 3H).
PAT
WIPO Patent Publication: WO2020231990A1 (and related family filings)
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020231990&_cid=P20-MUHRQT-01820-1
PAT
United States Patents: US11780845
PAT
US20230192709
https://patentscope.wipo.int/search/en/detail.jsf?docId=US399951539&_cid=P20-MUHRKD-96615-1
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References
[1]. Vivek Subbiah, et al. RLY-4008, the First Highly Selective FGFR2 Inhibitor with Activity across FGFR2 Alterations and Resistance Mutations. Cancer Discov. 2023 Sep 6;13(9):2012-2031. [Content Brief]
/////////lirafugratinib, anax labs, FDA 2026, APPROVALS 2026, Lyrfigtu, RLY-4008, RLY 4008, 23SEPT2026, CANCER
#lirafugratinib, #anax labs, #FDA 2026, #APPROVALS 2026, #Lyrfigtu, #RLY-4008, #RLY 4008, #23SEPT2026, #CANCER
Floretyrosine F 18
Floretyrosine F 18
CAS 178433-03-9
FormulaC₁₁H₁₄[¹⁸F]NO₃
Molecular Weight226.23 g/mol
FDA UNII1326R5J1IA
FDA 2026, APPROVALS 2026, Pixclara, TELIX PHARMACEUTICALS, GLIOMA, CANCER, TLX101-CDx, TLX101-Px, 1326R5J1IA, L-(18F)FET, O-(2-((18)F)fluoroethyl)-L-tyrosine
(2S)-2-amino-3-[4-(2-[¹⁸F]fluoroethoxy)phenyl]propanoic acid, (2S)-2-amino-3-[4-(2-(18F)fluoroethoxy)phenyl]propanoic acid
To use with positron emission tomography to differentiate recurrent or progressive glioma from treatment-related change in conjunction with other diagnostic evaluations
Floretyrosine F 18 (brand name Pixclara®, also known as 18F-FET) is a newly FDA-approved radiopharmaceutical imaging drug used in positron emission tomography (PET) scans for patients with glioma (brain cancer). Developed by Telix Pharmaceuticals, it received formal U.S. Food and Drug Administration (FDA) approval on September 14, 2026, making it the first and only approved FET-PET diagnostic tracer for brain tumors in the United States.
Primary Clinical Indication
Pixclara is indicated for use in both adult and pediatric patients (1 month of age and older).
Its primary clinical purpose is to differentiate recurrent or progressive glioma from treatment-related changes (such as radiation necrosis or inflammation). Following chemotherapy or radiation, traditional MRI scans often show areas that “light up,” making it incredibly difficult for neuro-oncologists to tell whether a tumor is growing back or if the brain is simply healing from harsh treatments. Pixclara solves this diagnostic dilemma by providing metabolic clarity.
How It Works (Mechanism of Action)
- Targeted Delivery: Floretyrosine F 18 is a synthetic amino acid analogue labeled with the radioactive isotope fluorine-18. [1, 2]
- Cellular Uptake: Once injected intravenously, it specifically targets and binds to L-type amino acid transporters 1 and 2 (LAT1 and LAT2). These transporters are heavily overexpressed on the membranes of active glioma cells compared to healthy brain tissue.
- PET Detection: The tumor cells rapidly absorb the tracer, and the energy emissions from the fluorine-18 isotope are captured by a PET scanner, creating a highly accurate metabolic map of the tumor.
Strategic & Future Impact
The approval aligns U.S. practice with international clinical guidelines—such as the National Comprehensive Cancer Network (NCCN) Guidelines®—which already recommend FET-PET imaging for brain tumor management. Furthermore, Telix Pharmaceuticals is currently conducting a Phase 3 registrational study to expand Pixclara’s indication to include the diagnosis and characterization of brain metastases (cancers that have spread to the brain from other parts of the body)
Fluoroethyl-l-tyrosine (18F), commonly known as [18F]FET, is a radiopharmaceutical tracer used in positron emission tomography (PET) imaging. This synthetic amino acid, labeled with the radioactive isotope fluorine-18, is a valuable radiopharmaceutical tracer for use in neuro-oncology for diagnosing, planning treatment, and following up on brain tumors such as gliomas. The tracer’s ability to provide detailed metabolic imaging of tumors makes it an essential tool in the clinical management of brain cancer patients. Continued advancements in PET imaging technology and the development of more efficient synthesis methods are expected to further enhance the clinical utility of [18F]FET.[2]
Radiosynthesis
There are two common pathways for the radiosynthesis of [18F]FET. The first one utilizes a nucleophilic 18F-fluorination of ethyleneglycol-1,2-ditosylate with a subsequent 18F-fluoroethylation of a precursor di-sodium salt of L-tyrosine. This sequence requires two purification steps, two different precursors and a dual-reactor synthesis module which is not widely available in research or commercial centers.[3][4][5] The schematic for this pathway is:[6]
The second route of radiosynthesis is a direct nucleophilic 18F-fluorination a TET (O-(2-tosyloxy-ethyl)-N-trityl-L-tyrosine tert-butyl ester) protected precursor followed by acidic hydrolysis of protecting groups.[3][4][7] The schematic for this pathway is:[6]
REF
- Fluorinated phenylalanines: synthesis and pharmaceutical applicationsPublication Name:Beilstein Journal of Organic ChemistryPublication Date:2020-05-15PMCID:PMC7237815PMID:32509033DOI:10.3762/bjoc.16.91
- Solid-Phase Synthesis of O-(2-[18F]-Fluoro-ethyl)-l-tyrosinePublication Name:SynfactsPublication Date:2013-03-15DOI:10.1055/s-0032-1318420
- Investigations into the synthesis, radiofluorination and conjugation of a new [18F]fluorocyclobutyl prosthetic group and its in vitro stability using a tyrosine model systemPublication Name:Bioorganic & Medicinal ChemistryPublication Date:2013-02-01PMID:23290251DOI:10.1016/j.bmc.2012.11.049
- Microfluidic technology: An economical and versatile approach for the synthesis of O-(2-[18F]fluoroethyl)-l-tyrosine ([18F]FET)Publication Name:Bioorganic & Medicinal Chemistry LettersPublication Date:2012-03-15PMID:22342141DOI:10.1016/j.bmcl.2012.01.083
- Synthesis and biological evaluation of novel F-18 labeled pyrazolo[1,5-a]pyrimidine derivatives: Potential PET imaging agents for tumor detectionPublication Name:Bioorganic & Medicinal Chemistry LettersPublication Date:2011-08-15PMID:21752641DOI:10.1016/j.bmcl.2011.06.072
- (18)F Labeled benzimidazole derivatives as potential radiotracer for positron emission tomography (PET) tumor imagingPublication Name:Bioorganic & Medicinal ChemistryPublication Date:2010-04-01PMID:20303769DOI:10.1016/j.bmc.2010.02.060
- No carrier added synthesis of O-(2′-[18F]fluoroethyl)-l-tyrosine via a novel type of chiral enantiomerically pure precursor, NiII complex of a (S)-tyrosine Schiff basePublication Name:Bioorganic & Medicinal ChemistryPublication Date:2008-05-01PMID:18378460DOI:10.1016/j.bmc.2008.03.040
- Solid-Phase Synthesis of O-(2-[18F]-Fluoro-ethyl)-l-tyrosine, DOI:10.1055/s-0032-1318420, Publication Date:2013, Publication Name:Synfacts
SYN
US20190223814/US249082034
PAT
US20120189546
https://patentscope.wipo.int/search/en/detail.jsf?docId=US73636763&_cid=P11-MU3HO5-37901-1
PAT
US20140235861
https://patentscope.wipo.int/search/en/detail.jsf?docId=US107206441&_cid=P11-MU3HO5-37901-1
Another example of an 18F-fluoroalkylation reaction to obtain a PET tracer is the reaction described by Wang et al (2006 J Radioanalyt Nuc Chem; 270(2): 439-43) used to obtain the 18F-labeled amino acid O-(2-[ 18F]fluoroethyl)-L-tyrosine ([ 18F]FET):
[ 18F]Fluoroethyl tosylate was prepared in step (i) by displacement of a tosyl group from 1,2-bistosyloxyethane by reaction with K 18F/Kryptofix 2.2.2 in acetonitrile at 90° C. for 10 minutes. The purified [ 18F]fluoroethyl tosylate was then reacted in step (ii) with a solution of L-tyrosine and 10% aqueous NaOH in DMSO (or di-Na-salt of L-tyrosine in DMSO) 20 minutes at 90° C. to obtain [ 18F]FET. In contrast to the method for preparation of 18F-labelled S-fluoroalkyl diarylguanidines as reported by Robins et al (supra), this method for preparation of [ 18F]FET uses a soluble base in the alkylation reaction. However, the reaction is still not ideal for carrying out on an automated synthesis device that uses a cassette due to the fact that and additional vial is required for the base used for the subsequent fluoroalkylation step.
PAT
Radiation radiation detector with position tracking system and its use in medical systems and proceduresPublication Number:
JP-2004512502-APriority Date:2000-08-21
- Novel imaging agents and precursors and methods of preparation thereofPublication Number:CN-1234680-CPriority Date:2001-06-04Grant Date:2006-01-04
- Radioactive emission detector equipped with a position tracking system and utilization thereof with medical systems and in medical proceduresPublication Number:US-2005055174-A1Priority Date:2000-08-21
- Radioactive emission detector equipped with a position tracking system and utilization thereof with medical systems and in medical proceduresPublication Number:US-7826889-B2Priority Date:2000-08-21Grant Date:2010-11-02
- Radioactive emission detector equipped with a position tracking system and utilization thereof with medical systems and in medical proceduresPublication Number:US-2004015075-A1Priority Date:2000-08-21
- Radioactive emission detector equipped with a position tracking systemPublication Number:US-2014249402-A1Priority Date:2000-08-21
- Tumor imaging compoundsPublication Number:CA-2479514-CPriority Date:2002-04-30Grant Date:2011-07-26
- Protected tyrosine derivatives, method for the production thereof and use of the same for producing o-(2-[18f]-fluoroethyl)-l-tyrosinePublication Number:WO-02102765-A3Priority Date:2001-06-05
- Protected tyrosine derivatives, method for the production thereof and use of the same for producing o-(2-[18f]-fluoroethyl)-l-tyrosinePublication Number:US-2004192954-A1Priority Date:2001-06-05
- PROTECTED TYROSINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR THE PRODUCTION OF O-(2-?18 F)-FLUORETHYL)-L-TYROSINEPublication Number:AT-E289992-T1Priority Date:2001-06-05Grant Date:2005-03-15
- Imaging agents, precursors thereof and methods of manufacturePublication Number:US-2003124059-A1Priority Date:2001-06-04
- Radioactively labelled amino acid analogues, their preparation and usePublication Number:US-2006127306-A1Priority Date:2002-08-02
- Radioactively labelled amino acid analogues, their preparation and usePublication Number:EP-1539250-A1Priority Date:2002-08-02
- Tumor imaging compoundsPublication Number:US-7989649-B2Priority Date:2002-04-30Grant Date:2011-08-02
- Tumor imaging compoundsPublication Number:US-2009240041-A1Priority Date:2002-04-30
- Tumor imaging compoundsPublication Number:US-7544715-B2Priority Date:2002-04-30Grant Date:2009-06-09
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References
- CID 54255856 from PubChem
- Treglia G, Muoio B, Giovanella L (2020). “18F-FET”. In Calabria F, Schillaci O (eds.). Radiopharmaceuticals: A Guide to PET/CT and PET/MRI. Cham: Springer International Publishing. pp. 83–88. doi:10.1007/978-3-030-27779-6_4. ISBN 978-3-030-27778-9.
- Bourdier T, Greguric I, Roselt P, Jackson T, Faragalla J, Katsifis A (July 2011). “Fully automated one-pot radiosynthesis of O-(2-[18F]fluoroethyl)-L-tyrosine on the TracerLab FX(FN) module”. Nuclear Medicine and Biology. 38 (5): 645–651. doi:10.1016/j.nucmedbio.2011.01.001. PMID 21718939.
- Siddiq IS, Atwa ST, Shama SA, Eltaoudy MH, Omar WM (March 2018). “Radiosynthesis and modified quality control of O-(2-[18F]fluoroethyl)-L-tyrosine ([18F]FET) for brain tumor imaging”. Applied Radiation and Isotopes. 133: 38–44. Bibcode:2018AppRI.133…38S. doi:10.1016/j.apradiso.2017.12.011. PMID 29275040.
- Wester HJ, Herz M, Weber W, Heiss P, Senekowitsch-Schmidtke R, Schwaiger M, et al. (January 1999). “Synthesis and radiopharmacology of O-(2-[18F]fluoroethyl)-L-tyrosine for tumor imaging”. Journal of Nuclear Medicine. 40 (1): 205–212. PMID 9935078.
- Wang M, Glick-Wilson BE, Zheng QH (December 2019). “Facile fully automated radiosynthesis and quality control of O-(2-[18F]fluoroethyl)-l-tyrosine ([18F]FET) for human brain tumor imaging”. Applied Radiation and Isotopes. 154 108852. Bibcode:2019AppRI.15408852W. doi:10.1016/j.apradiso.2019.108852. PMID 31442794.
- Mueller D, Klette I, Kalb F, Baum RP (July 2011). “Synthesis of O-(2-[18F]fluoroethyl)-L-tyrosine based on a cartridge purification method”. Nuclear Medicine and Biology. 38 (5): 653–658. doi:10.1016/j.nucmedbio.2011.01.006. PMID 21718940.
- Muoio B, Giovanella L, Treglia G (2018-09-04). “Recent Developments of 18F-FET PET in Neuro-oncology”. Current Medicinal Chemistry. 25 (26): 3061–3073. doi:10.2174/0929867325666171123202644. PMID 29173147.
- Wang L, Lieberman BP, Ploessl K, Kung HF (January 2014). “Synthesis and evaluation of ¹⁸F labeled FET prodrugs for tumor imaging”. Nuclear Medicine and Biology. 41 (1): 58–67. doi:10.1016/j.nucmedbio.2013.09.011. PMC 3895945. PMID 24183614.
- Lee TS, Ahn SH, Moon BS, Chun KS, Kang JH, Cheon GJ, et al. (August 2009). “Comparison of 18F-FDG, 18F-FET and 18F-FLT for differentiation between tumor and inflammation in rats”. Nuclear Medicine and Biology. 36 (6): 681–686. doi:10.1016/j.nucmedbio.2009.03.009. PMID 19647174.
- Leung K (2004), “O-(2-[18F]Fluoroethyl)-L-tyrosine”, Molecular Imaging and Contrast Agent Database (MICAD), Bethesda (MD): National Center for Biotechnology Information (US), PMID 20641653, retrieved 2024-07-10
- Heiss P, Mayer S, Herz M, Wester HJ, Schwaiger M, Senekowitsch-Schmidtke R (August 1999). “Investigation of transport mechanism and uptake kinetics of O-(2-[18F]fluoroethyl)-L-tyrosine in vitro and in vivo”. Journal of Nuclear Medicine. 40 (8): 1367–1373. PMID 10450690.
- Wang HE, Wu SY, Chang CW, Liu RS, Hwang LC, Lee TW, et al. (May 2005). “Evaluation of F-18-labeled amino acid derivatives and [18F]FDG as PET probes in a brain tumor-bearing animal model”. Nuclear Medicine and Biology. 32 (4): 367–375. doi:10.1016/j.nucmedbio.2005.01.005. PMID 15878506.
- Rau FC, Weber WA, Wester HJ, Herz M, Becker I, Krüger A, et al. (August 2002). “O-(2-[(18)F]Fluoroethyl)- L-tyrosine (FET): a tracer for differentiation of tumour from inflammation in murine lymph nodes”. European Journal of Nuclear Medicine and Molecular Imaging. 29 (8): 1039–1046. doi:10.1007/s00259-002-0821-6. PMID 12173018.
- Holzgreve A, Brendel M, Gu S, Carlsen J, Mille E, Böning G, et al. (2016-06-14). “Monitoring of Tumor Growth with [(18)F]-FET PET in a Mouse Model of Glioblastoma: SUV Measurements and Volumetric Approaches”. Frontiers in Neuroscience. 10: 260. doi:10.3389/fnins.2016.00260. PMC 4906232. PMID 27378835.
- “Product Characteristic of IASOglio©” (PDF). synektik.com.pl. 28 June 2024. Retrieved 28 June 2024.
- Pauleit D, Floeth F, Herzog H, Hamacher K, Tellmann L, Müller HW, et al. (April 2003). “Whole-body distribution and dosimetry of O-(2-[18F]fluoroethyl)-L-tyrosine”. European Journal of Nuclear Medicine and Molecular Imaging. 30 (4): 519–524. doi:10.1007/s00259-003-1118-0. PMID 12589478.
- Tang G, Tang X, Wang M, Luo L, Gan M (January 2004). “Radiation dosimetry of O-(3-[18F]fluoropropyl)-L-tyrosine as oncologic PET tracer based on the mice distribution data”. Applied Radiation and Isotopes. 60 (1): 27–32. doi:10.1016/j.apradiso.2003.10.005. PMID 14687633.
- Mattsson S, Johansson L, Leide Svegborn S, Liniecki J, Noßke D, Riklund KÅ, et al. (July 2015). “Radiation Dose to Patients from Radiopharmaceuticals: a Compendium of Current Information Related to Frequently Used Substances” (PDF). Annals of the ICRP. 44 (2 Suppl): 7–321. doi:10.1177/0146645314558019. PMID 26069086.
- “IASOglio”. Curium Pharma. Retrieved 2024-07-10.
 | |
| Clinical data | |
|---|---|
| Other names | 18F-FET; O-(2-(18F)fluoroethyl)-l-tyrosine, O-(2-Fluorethyl)-l-thyrosine, l-(18F)FET[1] |
| Routes of administration | Intravenous |
| ATC code | V09IX10 (WHO) |
| Identifiers | |
| IUPAC name | |
| CAS Number | 178433-03-9 |
| PubChem CID | 9834479 |
| ChemSpider | 8010200 |
| UNII | 1326R5J1IA |
| CompTox Dashboard (EPA) | DTXSID601045942 |
| Chemical and physical data | |
| Formula | C11H14FNO3 |
| Molar mass | 227.235 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
///////////floretyrosine F 18, anax labs, FDA 2026, APPROVALS 2026, Pixclara, TELIX PHARMACEUTICALS, GLIOMA, CANCER, TLX101-CDx, TLX101-Px, 1326R5J1IA, L-(18F)FET, O-(2-((18)F)fluoroethyl)-L-tyrosine
#floretyrosine F 18, #anax labs, #FDA 2026, #APPROVALS 2026, #Pixclara, #TELIX PHARMACEUTICALS, #GLIOMA, #CANCER, #TLX101-CDx, #TLX101-Px, #1326R5J1IA, #L-(18F)FET, #O-(2-((18)F)fluoroethyl)-L-tyrosine
Rusfertide
Rusfertide
MF
C114H181N27O28S2 MW 2442.0 g/mol
isovaleryl-Asp-Thr-His-Phe-Pro-Cys(1)-Ile-Lys(2)-Phe-Glu-Pro-Arg-Ser-Lys-Gly-Cys(1)-Lys-NH2.palmitoyl-Glu(2)-OH
(2S)-5-[4-[(3S,6S,9S,12S,15R,20R,26S,29S,32S,35S)-26-(4-aminobutyl)-6-benzyl-12-[(2S)-butan-2-yl]-32-(3-carbamimidamidopropyl)-3-(2-carboxyethyl)-15-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-3-carboxy-2-(3-methylbutanoylamino)propanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]-20-[[(2S)-1,6-diamino-1-oxohexan-2-yl]carbamoyl]-29-(hydroxymethyl)-2,5,8,11,14,22,25,28,31,34-decaoxo-17,18-dithia-1,4,7,10,13,21,24,27,30,33-decazabicyclo[33.3.0]octatriacontan-9-yl]butylamino]-2-(hexadecanoylamino)-5-oxopentanoic acid
{Asp(N-(3-methyl-1-oxobutyl))}-Thr-His-Phe-Pro-Cys-Ile-{Lys(γGlu-C16 acid)}-Phe-Glu-Pro-Arg-Ser-Lys-Gly-Cys-Lys-NH2 (disulfide bridge: Cys6-Cys16)
Mimrylo, APPROVALS 2026, FDA 2026, XM71MYX0IQ, PTG-300FB, PTG-300, TAK 121,
To treat erythrocytosis in adults with polycythemia vera
Rusfertide is a peptide mimetic of natural hepcidin, which targets and degrades ferroportin, reduces serum iron and transferrin-saturation, and thus regulates the production of red blood cells. Rusfertide ameliorates the polycythemia vera, β-thalassemia and hereditary hemochromatosis.
Rusfertide is an injectable peptide mimetic of hepcidin (hepcidin antimicrobial peptide; HAMP; putative liver tumor regressor; PLTR; liver-expressed antimicrobial peptide 1; LEAP-1) with potential use in the treatment of iron deficiency anemia and iron overload secondary to hematologic disorders. Upon administration, rusfertide mimics endogenous hepcidin, a protein primarily produced in hepatocytes, and increases hepcidin levels. As hepcidin plays a key role in the homeostasis of systemic iron, rusfertide may serve to normalize iron levels. Low levels of endogenous hepcidin are associated with iron overload secondary to excessive absorption of iron as seen in beta thalassemia and paradoxically with iron deficiency anemia.
Rusfertide, sold under the brand name Mimrylo, is a medication developed by Protagonist Therapeutics in partnership with Takeda for the treatment of polycythemia vera (PV).[1][2][3]
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References
 | |
| Clinical data | |
|---|---|
| Trade names | Mimrylo |
| Other names | PTG-300; TAK-121 |
| Identifiers | |
| CAS Number | 1628323-80-7 |
| PubChem CID | 155884410 |
| DrugBank | DB17724 |
| ChemSpider | 129955617 |
| UNII | XM71MYX0IQ |
| KEGG | D12064 |
| ChEMBL | ChEMBL4650507 |
| Chemical and physical data | |
| Formula | C114H181N27O28S2 |
| Molar mass | 2441.98 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
References
- “Rusfertide – Protagonist Therapeutics”. AdisInsight. Springer Nature Switzerland AG.
- Kremyanskaya M, Ginzburg YZ, Hoffman R (March 2026). “Modulators of the hepcidin pathway in polycythemia vera and myelofibrosis”. Blood. 147 (12): 1278–1288. doi:10.1182/blood.2025028643. PMID 41100735.
- “Protagonist and Takeda Announce ASCO Plenary Presentation Highlighting Full 32-Week Results from Phase 3 VERIFY Study of Rusfertide, Showing Reductions in Phlebotomy, Improved Hematocrit Control in Polycythemia Vera”. Takeda.
//////rusfertide, anax labs, Mimrylo, APPROVALS 2026, FDA 2026, XM71MYX0IQ, PTG-300FB, PTG 300, TAK 121,
#rusfertide, #anax labs, #Mimrylo, #APPROVALS 2026, #FDA 2026, #XM71MYX0IQ, #PTG-300FB, #PTG-300, #TAK 121,
Brepocitinib
Brepocitinib
CAS 1883299-62-4
MF C18H21F2N7O MW389.4 g/mol
8/27/2026, APPROVALS 2026, FDA 2026, Lisraya, PF 06700841, 3X8387Q25N, PF-06700841
[(1S)-2,2-difluorocyclopropyl]-[(1R,5S)-3-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone
- [(1S)-2,2-difluorocyclopropyl]-[(1S,5R)-3-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone
- Methanone, ((1S)-2,2-difluorocyclopropyl)(3-(2-((1-methyl-1H-pyrazol-4-yl)amino)-4-pyrimidinyl)-3,8-diazabicyclo(3.2.1)oct-8-yl)-
- ((1S)-2,2-difluorocyclopropyl)-((1S,5R)-3-(2-((1-methylpyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo(3.2.1)octan-8-yl)methanone
To treat dermatomyositis in adults
Brepocitinib (brand name Lisraya) is an oral, once-daily dual TYK2/JAK1 inhibitor approved by the FDA for treating dermatomyositis in adults.
Developed by Roivant (via its subsidiary Priovant), it is the first oral targeted therapy indicated to manage this rare, debilitating autoimmune condition. Brepocitinib, sold under the brand name Lisraya, is a drug which acts as a dual inhibitor of JAK1 and TYK2, and was developed for the treatment of plaque psoriasis.[1][2][3][4] It is used for the treatment of dermatomyositis.
Brepocitinib is an orally available, selective inhibitor of non-receptor tyrosine-protein kinase TYK2 (tyrosine kinase 2) and tyrosine-protein kinase JAK1 (Janus kinase 1; JAK1) with potential immunomodulatory and anti-inflammatory activities. Upon oral administration, brepocitinib selectively binds to and inhibits the activation of TYK2 and JAK1, thereby disrupting TYK2 and JAK-1-dependent cytokine signaling. This may reduce inflammatory responses and prevent inflammation-induced damage caused by certain immunological diseases. TYK2 and JAK-1 are members of the Janus kinase family of non-receptor tyrosine kinases and are involved in signaling pathways affecting hematopoiesis, immunity and inflammation.
SYN
Dual Inhibition of TYK2 and JAK1 for the Treatment of Autoimmune Diseases: Discovery of ((S)-2,2-Difluorocyclopropyl)((1R,5S)-3-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone (PF-06700841)
By: Fensome, Andrew ; et al
Journal of Medicinal Chemistry (2018), 61(19), 8597-8612
SYN
Preparation of aminopyrimidinyl derivatives as inhibitors of JAK kinases useful in therapy of diseases
Assignee: Pfizer Inc.
Inventors: Fensome, Andrew; et al
World Intellectual Property Organization
Patent#WO2016027195 A1
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2016027195&_cid=P11-MTCC5U-40903-1
SYN
https://www.sciencedirect.com/science/article/abs/pii/S0223523423008152
SYN
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US159751917&_cid=P11-MTCCDC-53135-1
Examples 7 and 8
[(1S)-2,2-difluorocyclopropyl][(1R,5S)-3-{2-[(1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-3,8-diazabicyclo[3.2.1]oct-8-yl]methanone and [(1R)-2,2-difluorocyclopropyl][(1R,5S)-3-{2-[(1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-3,8-diazabicyclo[3.2.1]oct-8-yl]methanone
Peak 1: Example 7
[(1S)-2,2-difluorocyclopropyl][(1R,5S)-3-{2-[(1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-3,8-diazabicyclo[3.2.1]oct-8-yl]methanone
PAT
- New compounds for the inhibition of angiogenesis and use of thereofPublication Number:AU-2005223356-A1Priority Date:2004-03-24
- Compositions and methods of use for modified release minoxidilPublication Number:US-2025325546-A1
- Aminopyrimidinyl compoundsPublication Number:US-10980815-B2Priority Date:2014-08-21Grant Date:2021-04-20
- Aminopyrimidinyl compounds as JAK inhibitorsPublication Number:MD-4800-C1Priority Date:2014-08-21
- Aminopyrimidinyl compoundsPublication Number:US-2020330477-A1Priority Date:2014-08-21
- Aminopyrimidinyl compoundsPublication Number:US-11197867-B2Priority Date:2014-08-21Grant Date:2021-12-14
- Aminopyrimidinyl compoundsPublication Number:TW-201609706-APriority Date:2014-08-21
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Discovery Solutions, Supporting the chemistry needs of clients in the Medical, Analytical and Bio Sciences
Development Solutions, Developing from Lab scale to PR&D, Kilo Scale-ups and Commercial Scales
SEE MORE………Integrated Solutions, Manufacturing Solutions, Products,
Can’t Find? Let’s Connect
Phone : +91 897704 2010 / +91 9177075735, Email : info@anaxlab.com
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References
References
- Fensome A, Ambler CM, Arnold E, Banker ME, Brown MF, Chrencik J, et al. (October 2018). “Dual Inhibition of TYK2 and JAK1 for the Treatment of Autoimmune Diseases: Discovery of (( S)-2,2-Difluorocyclopropyl)((1 R,5 S)-3-(2-((1-methyl-1 H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone (PF-06700841)”. Journal of Medicinal Chemistry. 61 (19): 8597–8612. doi:10.1021/acs.jmedchem.8b00917. PMID 30113844.
- Forman SB, Pariser DM, Poulin Y, Vincent MS, Gilbert SA, Kieras EM, et al. (December 2020). “TYK2/JAK1 Inhibitor PF-06700841 in Patients with Plaque Psoriasis: Phase IIa, Randomized, Double-Blind, Placebo-Controlled Trial”. The Journal of Investigative Dermatology. 140 (12): 2359–2370.e5. doi:10.1016/j.jid.2020.03.962. PMID 32311398.
- Martin G (February 2023). “Novel Therapies in Plaque Psoriasis: A Review of Tyrosine Kinase 2 Inhibitors”. Dermatology and Therapy. 13 (2): 417–435. doi:10.1007/s13555-022-00878-9. PMC 9884727. PMID 36592300.
- Caso F, Costa L, Triggianese P, Maione F, Bertolini N, Vastarella M, et al. (May 2023). “Recent developments for new investigational JAK inhibitors in psoriatic arthritis”. Expert Opinion on Investigational Drugs. 32 (5): 361–371. doi:10.1080/13543784.2023.2207737. PMID 37096862.
 | |
| Clinical data | |
|---|---|
| Trade names | Lisraya |
| Other names | PF-06700841 |
| Identifiers | |
| IUPAC name | |
| CAS Number | 1883299-62-4 |
| PubChem CID | 118878093 |
| DrugBank | DB15003 |
| ChemSpider | 72380129 |
| UNII | 3X8387Q25N |
| ChEMBL | ChEMBL4297477 |
| Chemical and physical data | |
| Formula | C18H21F2N7O |
| Molar mass | 389.411 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
///////////brepocitinib, anax labs, APPROVALS 2026, FDA 2026, Lisraya, PF 06700841, 3X8387Q25N, PF-06700841, dermatomyositis
#brepocitinib, #anax labs, #APPROVALS 2026, #FDA 2026, #Lisraya, #PF 06700841, #3X8387Q25N, #PF-06700841, #dermatomyositis
