Amsulostat

CAS 2409963-83-1

MF C13H13FN2O2S MW280.32

2-Buten-1-amine, 3-fluoro-4-(8-quinolinylsulfonyl)-, (2Z)-

(2Z)-3-fluoro-4-(quinolin-8-ylsulfonyl)but-2-en-1-amine

(Z)-3-fluoro-4-quinolin-8-ylsulfonylbut-2-en-1-amine

(2Z)-3-fluoro-4-(quinolin-8-ylsulfonyl)but-2-en-1-amine
protein-lysine-oxidase (LOX) inhibitor, antifibrotic,  PXS 5505, LOX inhibitor PXS-5505, LOX-IN-3, pan-LOX inhibitor PXS-5505, DO94E28WYW, SNT 5505

Amsulostat is an orally available, small-molecule, irreversible inhibitor of all lysyl oxidases (LOX) family members, with potential antifibrotic activity. Upon oral administration, amsulostat targets, binds to and inhibits the activity of all enzymes in the LOX family. This prevents the post-translational oxidative deamination of lysine residues on target proteins, including collagen and elastin, and reduces the formation of deaminated lysine (allysine), the formation of inter- and intramolecular cross-linkages and may prevent remodeling of the extracellular matrix (ECM), thereby reducing fibrotic tissue formation in certain chronic fibrotic diseases. LOX is often upregulated in fibrotic tissue and plays a key role in fibrosis.

Amsulostat (formerly PXS-5505) is an orally available, investigational, pan-lysyl oxidase (pan-LOX) inhibitor designed by Syntara to treat fibrotic diseases and solid tumors. It works by preventing collagen cross-linking and remodeling of the extracellular matrix, effectively reducing fibrosis. The drug is currently in Phase 2 clinical trials for myelofibrosis, showing promise in reducing symptom burden and spleen volume, and is also being studied for myelodysplastic syndrome (MDS) and pancreatic cancer. 

Key Aspects of Amsulostat:

• Mechanism of Action: Irreversibly inhibits all LOX family members (LOX, LOXL1-4), reducing fibrotic tissue.
• Clinical Status (Myelofibrosis): Phase 2a data showed 73% of patients (who were suboptimal responders to ruxolitinib) achieved  reduction in total symptom score, with significant spleen volume reduction.
• Clinical Status (Other Cancers): Phase 2 trials (AZALOX) are evaluating its use in myelodysplastic syndrome (MDS) and chronic myelomonocytic leukemia (CMML). It is also being tested in combination with chemotherapy for pancreatic cancer to improve drug delivery to tumors.
• Regulatory Status: Has received Orphan Drug Designation for primary myelofibrosis from the FDA (USA) and EMA (Europe).
• Safety Profile: Clinical trials have reported it is well-tolerated with no treatment-related serious adverse events in early findings.

Amsulostat’s ability to target the stiff, fibrotic environment surrounding tumors makes it a promising “add-on” therapy to increase the effectiveness of existing cancer treatments, including chemotherapy and immunotherapy.

An orally available, small-molecule, irreversible inhibitor of all lysyl oxidases (LOX) family members, with potential antifibrotic activity. Upon oral administration, amsulostat targets, binds to and inhibits the activity of all enzymes in the LOX family. This prevents the post-translational oxidative deamination of lysine residues on target proteins, including collagen and elastin, and reduces the formation of deaminated lysine (allysine), the formation of inter- and intramolecular cross-linkages and may prevent remodeling of the extracellular matrix (ECM), thereby reducing fibrotic tissue formation in certain chronic fibrotic diseases. LOX is often upregulated in fibrotic tissue and plays a key role in fibrosis.

SYN

US12178791,

Compound 33

syn

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020024017&_cid=P20-MNDZVP-86742-1

(Z)-3-fluoro-4-(quinolin-8-ylsulfonyl)but-2-en-1-amine dihydrochloride (Compound 33)

[0282] White solid; m.p.150-153 °C; ¹H NMR (300 MHz, CD3OD) d ppm: 9.18 (d, J = 4.7 Hz, 1H), 8.70 (dd, J = 8.4, 2.6 Hz, 1H), 8.57 (d, J = 7.4 Hz, 1H), 8.45 (d, J = 8.5 Hz, 1H), 7.99– 7.68 (m, 2H), 5.22 (dt, J = 32.9, 7.4 Hz, 1H), 5.00 (d, J = 19.4 Hz, 2H), 3.60 (d, J = 7.7 Hz, 2H); LCMS: for C₁₃H₁₃FN₂O₂S calculated 280.1, found 281.1 [M+1]⁺.

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References

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////////////amsulostat, ANAX LAB, protein-lysine-oxidase (LOX) inhibitor, antifibrotic,  PXS 5505, LOX inhibitor PXS-5505, LOX-IN-3, pan-LOX inhibitor PXS-5505, DO94E28WYW, SNT 5505