ThioTEPA

Drugbox
IUPAC_name = 1,1',1"-phosphorothioyltriaziridine

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width=180
CAS_number=52-24-4
ATC_prefix=L01
ATC_suffix=AC01
ATC_supplemental=
PubChem=5453
DrugBank=
C = 6 | H = 12 | N = 3 | P = 1 | S = 1
molecular_weight = 189.219 g/mol
bioavailability=
metabolism = Hepatic (CYP2B6, CYP2C11)
elimination_half-life=2.4 hours
15-18 hours (metabolites)
excretion = Renal
pregnancy_AU = D
pregnancy_US = D
legal_UK = POM
legal_US = Rx-only
routes_of_administration= 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.

References

*cite journal | author = Sykes M "et al". | title = Clinical Studies of triethylenephosphoramide compounds with nitrogen mustard-like activity | journal = Cancer | volume = 6 | issue = | pages = 142–48 | year = 1953 | doi = 10.1002/1097-0142(195301)6:1<142::AID-CNCR2820060114>3.0.CO;2-W | doilabel = 10.1002/1097-0142(195301)6:1142::AID-CNCR28200601143.0.CO;2-W
*cite journal | author = Maanen MJ, Smeets CJ, Beijnen JH | title = Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA) | journal = Cancer Treat Rev | volume = 26 | issue = 4 | pages = 257–68 | year = 2000 | pmid = 10913381 | doi = 10.1053/ctrv.2000.0170