Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1583)
Drug Name
Thiotepa
Synonyms
Tespamin; Tespamine; Thio-Tep; Thio-tepa S; Thiofozil; Thiophosphamide; Thiophosphamidum; Thioplex; Thiotef; Thiotriethylenephosphoramide; Girostan; Ledertepa; Oncotepa; Oncothio-tepa; Oncotiotepa; THIO-TEPA; TIO TEF; Tifosyl; Tio-tef; Tiofosfamid; Tiofosyl; Tiofozil; Triethylene thiophosphoramide; Triethylenethiophosphoramide; thiotepa; 1,1',1''-phosphorothioyltriaziridine; 52-24-4; N,N',N''-Triethylenethiophosphoramide; Stepa; TESPA; TSPA; Tri(aziridin-1-yl)phosphine sulfide; Tris(1-aziridinyl)phosphine sulfide
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 189.22 Topological Polar Surface Area 41.1
Heavy Atom Count 11 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5453
PubChem SID
9843 ; 72371 ; 649541 ; 3140674 ; 5647700 ; 7847649 ; 7980777 ; 8149979 ; 8153354 ; 11335992 ; 11361231 ; 11364583 ; 11367145 ; 11369707 ; 11372787 ; 11373954 ; 11377869 ; 11417492 ; 11462203 ; 11485170 ; 11489373 ; 11491409 ; 11492023 ; 11495503 ; 15322228 ; 24900346 ; 26612468 ; 26679451 ; 26748780 ; 26748781 ; 26748782 ; 26753739 ; 29224498 ; 46505958 ; 47736527 ; 48259276 ; 48334538 ; 48414528 ; 48416616 ; 48424268 ; 49854391 ; 50107461 ; 53663888 ; 53789872 ; 57260086 ; 57264451 ; 57322788 ; 68530579 ; 83572147 ; 88826535
ChEBI ID
CHEBI:9570
CAS Number
52-24-4
TTD Drug ID
D00YZA
Formula
C6H12N3PS
Canonical SMILES
C1CN1P(=S)(N2CC2)N3CC3
InChI
1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
InChIKey
FOCVUCIESVLUNU-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Thiotepa Metabolite b DM004617 N. A. Unclear 1 [4]
Thiotepa Metabolite d DM004623 N. A. Unclear 1 [4]
1,2,3-TrichloroTEPA DM004618 N. A. Unclear 2 [5]
1,2DichloroTEPA DM004627 N. A. Unclear 2 [4]
Thiotepa Metabolite c DM004626 N. A. Unclear 2 [4]
Thiotepa Metabolite e DM004624 N. A. Unclear 2 [4]
DechloroethyltrichloroTEPA DM004619 N. A. Unclear 3 [5]
Thiotepa Metabolite f DM004625 N. A. Unclear 3 [4]
Chloroacetaldchyde DM004620 N. A. Unclear 4 [5]
SCMC DM004621
1080
Unclear 5 [5]
TDGA DM004622
31277
Unclear 6 [5]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004962 Thiotepa Thiotepa Metabolite b Unclear Unclear [4]
MR004968 Thiotepa Thiotepa Metabolite d Unclear Unclear [4]
MR004963 Thiotepa Metabolite b 1,2,3-TrichloroTEPA Unclear Unclear [5]
MR004971 Thiotepa Metabolite b Thiotepa Metabolite c Unclear Unclear [4]
MR004972 Thiotepa Metabolite b 1,2DichloroTEPA Unclear Unclear [4]
MR004969 Thiotepa Metabolite d Thiotepa Metabolite e Unclear Unclear [4]
MR004964 1,2,3-TrichloroTEPA DechloroethyltrichloroTEPA Unclear Unclear [5]
MR004965 1,2,3-TrichloroTEPA Chloroacetaldchyde Unclear Unclear [5]
MR004970 Thiotepa Metabolite e Thiotepa Metabolite f Unclear AANAT [4]
MR004966 Chloroacetaldchyde SCMC Unclear Unclear [5]
MR004967 SCMC TDGA Unclear Unclear [5]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[3]
Serotonin N-acetyltransferase (AANAT) DMEN242 Homo sapiens
SNAT_HUMAN
2.3.1.87
[4]
References
1 Thiotepa was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Cytochrome P450 isozymes 3A4 and 2B6 are involved in the in vitro human metabolism of thiotepa to TEPA. Cancer Chemother Pharmacol. 2002 Jun;49(6):461-7.
3 Differential catalytic efficiency of allelic variants of human glutathione S-transferase Pi in catalyzing the glutathione conjugation of thiotepa. Arch Biochem Biophys. 1999 Jun 1;366(1):89-94.
4 Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA)
5 A comprehensive understanding of thioTEPA metabolism in the mouse using UPLC-ESI-QTOFMS-based metabolomics

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