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

General Information of Drug (ID: DR5501)
Drug Name
Fotemustine
Synonyms
Fotemustine; 92118-27-9; Diethyl (1-(3-(2-chloroethyl)-3-nitrosoureido)ethyl)phosphonate; Muphoran; Mustophorane; Servier-10036; Fotemustinum [Latin]; Fotemustina [Spanish]; S 10036; C9H19ClN3O5P; CCRIS 6337; S-10036; Fotemustinum; Diethyl-1-(3-(2-chloroethyl)-3-nitrosoureido)ethylphosphonate; (+-)-Diethyl (1-(3-(2-chloroethyl)-3-nitrosoureido)ethyl)phosphonate; Mustoforan; 1-(2-chloroethyl)-3-(1-diethoxyphosphorylethyl)-1-nitrosourea; Fotemustine [BAN:INN]
Indication Solid tumour/cancer [ICD11: 2A00-2F9Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 315.69 Topological Polar Surface Area 97.3
Heavy Atom Count 19 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
104799
ChEBI ID
CHEBI:131852
CAS Number
92118-27-9
TTD Drug ID
D0S1ZB
Formula
C9H19ClN3O5P
Canonical SMILES
CCOP(=O)(C(C)NC(=O)N(CCCl)N=O)OCC
InChI
InChI=1S/C9H19ClN3O5P/c1-4-17-19(16,18-5-2)8(3)11-9(14)13(12-15)7-6-10/h8H,4-7H2,1-3H3,(H,11,14)
InChIKey
YAKWPXVTIGTRJH-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
Choroethanol DM017557 N. A. Unclear - Unclear 1 [2]
DEP-isocyanate DM017554 N. A. Unclear - Unclear 1 [3]
NIEDP DM017552 N. A. Unclear - Unclear 1 [2]
Fotemustine metabolite II DM017555 N. A. Unclear - Unclear 2 [3]
IEDP DM016484
101669216
Unclear - Unclear 2 [2]
DEP-SG DM017556 N. A. Unclear - Unclear 3 [3]
Fotemustine metabolite VI DM016483
101669215
Unclear - Unclear 3 [4]
HEDP DM017553 N. A. Unclear - Unclear 3 [2]
Acetic acid DM001682
176
Unclear - Unclear 4 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008926 Fotemustine NIEDP Unclear - Unclear Unclear [2]
MR008930 Fotemustine DEP-isocyanate Unclear - Unclear Unclear [3]
MR008934 Fotemustine Choroethanol Unclear - Unclear Unclear [2]
MR008931 DEP-isocyanate Fotemustine metabolite II Unclear - Unclear Unclear [3]
MR008927 NIEDP IEDP Unclear - Unclear Unclear [2]
MR008932 Fotemustine metabolite II DEP-SG Unclear - Unclear Unclear [3]
MR008933 Fotemustine metabolite II Fotemustine metabolite VI Unclear - Unclear Unclear [4]
MR008928 IEDP HEDP Unclear - Unclear Unclear [2]
MR008929 HEDP Acetic acid Unclear - Unclear Unclear [2]
⏷ Show the Full List of 9 MR(s)
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Disposition, pharmacokinetics, and metabolism of 14C-fotemustine in cancer patients
3 Molecular mechanisms of toxic effects of fotemustine in rat hepatocytes and subcellular rat liver fractions
4 Chemical and glutathione conjugation-related degradation of fotemustine: formation and characterization of a glutathione conjugate of diethyl (1-isocyanatoethyl)phosphonate, a reactive metabolite of fotemustine

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