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

General Information of Drug (ID: DR0278)
Drug Name
Carmustine
Synonyms
Carmubris; Carmustin; Carmustina; Carmustina [INN-Spanish]; Carmustinum; Carmustinum [INN-Latin]; DTI 015; Gliadel; Becenum; Becenun; Bi CNU; BiCNU (TN); Bis(2-chloroethyl)nitrosourea; Bischlorethylnitrosourea; Bischlorethylnitrosurea; Bischloroethyl nitrosourea; Bischloroethylnitrosourea; Gliadel Wafer; Nitrumon; SRI 1720; carmustine; 1,3-Bis(2-chloroethyl)-1-nitrosourea; 1,3-Bis(2-chloroethyl)nitrosourea; 154-93-8; BCNU; BiCNU; FDA 0345; N,N'-BIS(2-CHLOROETHYL)-N-NITROSOUREA; NCI-C04773; Urea, N,N'-bis(2-chloroethyl)-N-nitroso-
Indication Hepatocellular carcinoma [ICD11: 2C12] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 214.05 Topological Polar Surface Area 61.8
Heavy Atom Count 12 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2578
ChEBI ID
CHEBI:3423
CAS Number
154-93-8
TTD Drug ID
D01OXI
Formula
C5H9Cl2N3O2
Canonical SMILES
N(C(=O)NCCCl)(N=O)CCCl.OCC
InChI
1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
InChIKey
DLGOEMSEDOSKAD-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
1,3-Bis(2-chloroethyl)urea DM000732
95791
Other reaction - Denitration 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000562 Carmustine 1,3-Bis(2-chloroethyl)urea Other reaction - Denitration GSTA1 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[3]
References
1 Carmustine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Principal drug-metabolizing enzyme systems in L1210 leukemia sensitive or resistant to BCNU in vivo. Leuk Res. 1994 Nov;18(11):829-35.
3 Expression of glutathione S-transferase T1 (GSTT1) in human brain tumours. Histol Histopathol. 2006 Nov;21(11):1199-207.
4 Metabolism of 1,3-bis(2-chloroethyl)-1-nitrosourea by rat hepatic microsomes J Med Chem. 1981 Jun;24(6):761-3. doi: 10.1021/jm00138a025.

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