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Thiotepa, チオテパ ,тиотепа , ثيوتيبا , 塞替派 ,

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ChemSpider 2D Image | thiotepa | C6H12N3PS

Thiotepa, チオテパ

  • Use:antineoplastic, alkylating agent
  • Chemical name:1,1′,1”-phosphinothioylidynetrisaziridine
  • Formula:C6H12N3PS
  • MW:189.22 g/mol
  • CAS:52-24-4
  • EINECS:200-135-7
  • LD50:14500 μg/kg (M, i.v.); 38 mg/kg (M, p.o.);
    9400 μg/kg (R, i.v.)
  • Aziridine, 1,1′,1”-phosphinothioylidynetris-
    Aziridine, 1-[bis(1-aziridinyl)phosphinothioyl]-
    N,N’,N”-Triethylenethiophosphoramide
    Phosphorothioic tri(ethyleneamide)
    SZ2975000
    T3NTJ APS&- AT3NTJ&- AT3NTJ [WLN]
    Thiofozil
    Thiotef
    1,1′,1”-Phosphorothioyltriaziridine

JAPAN APPROVED, Rethio, PMDA, 2019/3/26

тиотепа [Russian] [INN]
ثيوتيبا [Arabic] [INN]
塞替派 [Chinese] [INN]

Thiotepa (INN,[1] chemical name: N,N′,N′′-triethylenethiophosphoramide) is an alkylating agent used to treat cancer.

Thiotepa is an organophosphorus compound with the formula SP(NC2H4)3.[2] It is an analog of N,N′,N′′-triethylenephosphoramide (TEPA), which contains tetrahedral phosphorus and is structurally akin to phosphate. It is manufactured by heating aziridine with thiophosphoryl chloride.

History

Thiotepa was developed by the American Cyanamid company in the early 1950s and reported to media outlets in 1953.[3] In 1959, thiotepa was registered with the Food and Drug Administration (FDA) as a drug therapy for several solid cancers.[4]

On January 29, 2007, the European Medicines Agency designated thiotepa as an orphan drug. On April 2, 2007, the United States FDA designated thiotepa as a conditioning treatment for use prior to hematopoietic stem cell transplantation.[5] Adienne Pharma & Biotech (Italy), the owner of thiotepa (Tepadina) applied for these designations.

Use

Thiotepa is indicated for use in combination with other chemotherapeutic agents. This can be with or without total body irradiation (TBI), as a conditioning treatment prior to allogeneic or autologous hematopoietic progenitor cell transplantation (HPCT) in hematological diseases in adult and pediatric patients. These diseases include Hodgkin’s disease and leukaemia. Thiotepa is also used with high-dose chemotherapy with HPCT support to treat certain solid tumors in adult and pediatric patients.[6]

Thiotepa is used in the palliation of many neoplastic diseases. The best results are found in the treatment of adenocarcinoma of the breast, adenocarcinoma of the ovarypapillary thyroid cancer and bladder cancer. Thiotepa is used to control intracavitary effusions caused by serosal neoplastic deposits.[6]

Intravesical use

Thiotepa is used as intravesical chemotherapy in bladder cancer.[7]

It may be used prophylactically to prevent seeding of tumor cells at cystoscopic biopsy; as an adjunctive agent at the time of biopsy; or as a therapeutic agent to prevent recurrence after cystoscopic resection of bladder tumor (transurethral resection of bladder tumor, TURBT). For intravesical use, thiotepa is given in 30 mg doses weekly, for four to six weeks. Efficacy in tumor control may reach 55 percent. The main toxicity of this therapy is bone marrow suppression due to systemic absorption of the drug.

Side effects

The main side effect of thiotepa is bone marrow suppression resulting in leukopeniathrombocytopenia and anemia.[8] Liver and lung toxicity may also occur.

SYN

Image result for thiotepa

NMR

<sup>1</sup>H NMR spectrum of C<sub>6</sub>H<sub>13</sub>N<sub>3</sub>P<sub></sub>S<sub></sub> in CDCL3 at 400 MHz.<br>Click to toggle size.

Fig 5. 1H NMR spectrum of C6H13N3PS in CDCL3 at 400 MHz.

R.J. Abraham, M. Mobli Modelling 1H NMR Spectra of Organic Compounds:
  Theory, Applications and NMR Prediction Software, Wiley, Chichester, 2008.

References

  1. ^ “International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary Names (Rec. I.N.N.): List 4” (PDF). World Health Organization. March 1962. p. 111. Retrieved 27 November 2016.
  2. ^ Maanen, M. J.; Smeets, C. J.; Beijnen, J. H. (2000). “Chemistry, pharmacology and pharmacokinetics of N,N’,N” -triethylenethiophosphoramide (ThioTEPA)”. Cancer Treatment Reviews26 (4): 257–268. doi:10.1053/ctrv.2000.0170PMID 10913381.
  3. ^ Sykes, M. P.; Karnofsky, D. A.; Philips, F. S.; Burchenal, J. H. (1953). “Clinical studies on triethylenephosphoramide and diethylenephosphoramide, compounds with nitrogen-mustard-like activity”. Cancer6 (1): 142–148. doi:10.1002/1097-0142(195301)6:1<142::AID-CNCR2820060114>3.0.CO;2-W.
  4. ^ Kim, Kyu-Won; Roh, Jae Kyung; Wee, Hee-Jun; Kim, Chan (2016). Cancer Drug Discovery: Science and History. Springer. p. 82. ISBN 978-94-024-0844-7.
  5. ^ “EMA Grants Adienne Marketing Rights for Tepadina”dddmag.com. Drug Discovery & Development. 19 March 2010. Retrieved 25 November 2011.
  6. Jump up to:a b “Urgent, thioTEPA update” (PDF)Food and Drug Administration. Adienne Pharma & Biotech. 5 April 2011. Retrieved 25 November 2011.
  7. ^ Droller M. Urothelial Tumors PMPH-USA, 2004. p. 207 ISBN 1550091735
  8. ^ Agnelli, G.; de Cunto, M.; Gresele, P.; del Favero, A. (1982). “Early onset life-threatening myelosuppression after low dose of intravesical thiotepa”Postgraduate Medical Journal58 (680): 380–381. doi:10.1136/pgmj.58.680.380PMC 2426344PMID 6812036.

External links

REF

US 2 670 347 (American Cyanamid; 1954; prior. 1952)

Thiotepa
ThioTEPA.svg
Clinical data
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a682821
License data
Pregnancy
category
  • AU: D
  • US: D (Evidence of risk)
Routes of
administration
IV, intracavitary, intravesical
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Hepatic (CYP2BCYP3A)
Elimination half-life 1.5–4.1 hours
Excretion Renal
6 hours for thiotepa
8 hours for TEPA
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.000.124 Edit this at Wikidata
Chemical and physical data
Formula C6H12N3PS
Molar mass 189.23 g/mol g·mol−1
3D model (JSmol)

//////////////Thiotepa, チオテパ   ,тиотепа ثيوتيبا 塞替派 , JAPAN 2019

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 year tenure till date Dec 2017, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 19 lakh plus views on New Drug Approvals Blog in 216 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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