ThioTEPA

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ThioTEPA
Systematic (IUPAC) name
1,1',1-phosphorothioyltriaziridine
Identifiers
CAS number	52-24-4
ATC code	L01AC01
PubChem	5453
Chemical data
Formula	C6H12N3PS
Mol. mass	189.219 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic (CYP2B6, CYP2C11)
Half life	2.4 hours 15-18 hours (metabolites)
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	D(AU) D(US)
Legal status	POM(UK) ℞-only(US)
Routes	IV, intracavitary, intravesical

N,N'N'-triethylenethiophosphoramide, abbreviated "ThioTEPA," is an organophosphorus compound with the formula SP(NC₂H₄)₃. This cancer chemotherapeutic member of the alkylating agent group has been in use for since the 1960s. It is an analogue of N,N',N''- triethylenephosphoramide (TEPA). It is mostly used to treat breast cancer, ovarian cancer, and bladder cancer. It is also used as conditioning for bone marrow transplantation. Its main toxicity is myelosuppression.

This molecule features tetrahedral phosphorus and is structurally akin to phosphate. It is derived from aziridine and thiophosphoryl chloride.

[edit] References

• Sykes M et al. (1953). "Clinical Studies of triethylenephosphoramide compounds with nitrogen mustard-like activity". Cancer 6: 142–48. doi:10.1002/1097-0142(195301)6:1<142::AID-CNCR2820060114>3.0.CO;2-W. 
• Maanen MJ, Smeets CJ, Beijnen JH (2000). "Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA)". Cancer Treat Rev 26 (4): 257–68. doi:10.1053/ctrv.2000.0170. PMID 10913381. 

v • d • e Chemotherapeutic agents/Antineoplastic agents (L01) Alkylating and alkylating-like agents Nitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan, Bendamustine, Uramustine) Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin) Platinum (alkylating-like): (Carboplatin, Cisplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin) Alkyl sulfonates:(Busulfan, Treosulfan) Hydrazines:(Procarbazine, Dacarbazine, Temozolomide) Aziridines:(ThioTEPA) Antimetabolites Folic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed) Purine: (Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine) Pyrimidine: (Cytarabine, Decitabine, Fluorouracil/Capecitabine, Floxuridine, Gemcitabine) Spindle poison/mitotic inhibitor Taxane: (Docetaxel, Larotaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine). Cytotoxic/antitumor antibiotics Anthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Pixantrone, Valrubicin) streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin) - Hydroxyurea Topoisomerase inhibitors Camptotheca: (Camptothecin, Topotecan, Irinotecan, Rubitecan), Podophyllum:(Etoposide, Teniposide) CI monoclonal antibodies Receptor tyrosine kinase (Cetuximab, Panitumumab, Trastuzumab) - CD20 (Rituximab, Tositumomab) - other (Alemtuzumab, Bevacizumab, Gemtuzumab) Photosensitizers Aminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin Tyrosine kinase inhibitors Axitinib, Bosutinib, Cediranib, Dasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Lestaurtinib, Nilotinib, Semaxanib, Sorafenib, Sunitinib, Vandetanib Cyclin-dependent kinase inhibitor Seliciclib Other retinoids (Alitretinoin, Tretinoin), Fusion protein (Aflibercept) - Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase (Pegaspargase), Bexarotene, Bortezomib, Celecoxib, Denileukin diftitox, Elesclomol, Estramustine, Irofulven, Ixabepilone, Masoprocol, Mitotane, Oblimersen, Testolactone, Tipifarnib, Trabectedin