thiotepa   Click here for help

GtoPdb Ligand ID: 7622

Synonyms: Tepadina® | Thioplex®
Approved drug
thiotepa is an approved drug (FDA (1959), EMA (2010))
Compound class: Synthetic organic
Comment: Thiotepa is an organophosphorus DNA alkylating anti-cancer chemotherapeutic [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 50.93
Molecular weight 189.05
XLogP 0.76
No. Lipinski's rules broken 0
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Canonical SMILES S=P(N1CC1)(N1CC1)N1CC1
Isomeric SMILES S=P(N1CC1)(N1CC1)N1CC1
InChI InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
1. Maanen MJ, Smeets CJ, Beijnen JH. (2000)
Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA).
Cancer Treat Rev, 26 (4): 257-68. [PMID:10913381]
2. Walsky RL, Obach RS. (2007)
A comparison of 2-phenyl-2-(1-piperidinyl)propane (ppp), 1,1',1''-phosphinothioylidynetrisaziridine (thioTEPA), clopidogrel, and ticlopidine as selective inactivators of human cytochrome P450 2B6.
Drug Metab Dispos, 35 (11): 2053-9. [PMID:17682072]