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

General Information of Drug (ID: DR0904)
Drug Name
Ketazolam
Synonyms
Ketazolamum; Ketazolamum [INN-Latin]; Loftran; U 28774; U-28,774; Unakalm; Anseren; Ansieten; KETAZOLAM; 11-Chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-(1,3)-oxazino(3,2-d)(1,4)benzodiazepine-4,7(6H)dione; 27223-35-4; 4H-(1,3)Oxazino(3,2-d)(1,4)benzodiazepine-4,7(6H)-dione, 8,12b-dihydro-11-chloro-2,8-dimethyl-12b-phenyl-; 4H-[1,3]Oxazino[3,2-d][1,4]benzodiazepine-4,7(6H)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-; Anxon; EINECS 248-346-3; NSC 338158
Indication Anxiety disorder [ICD11: 6B00] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 368.8 Topological Polar Surface Area 49.8
Heavy Atom Count 26 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
33746
ChEBI ID
CHEBI:135556
CAS Number
27223-35-4
Formula
C20H17ClN2O3
Canonical SMILES
CC1=CC(=O)N2CC(=O)N(C3=C(C2(O1)C4=CC=CC=C4)C=C(C=C3)Cl)C
InChI
1S/C20H17ClN2O3/c1-13-10-18(24)23-12-19(25)22(2)17-9-8-15(21)11-16(17)20(23,26-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3
InChIKey
PWAJCNITSBZRBL-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
Diazepam DM003056
3016
Oxidation - Degradation 1 [3]
Desmethyldiazepam DM000834
2997
Unclear 2 [3] , [4]
Medazepam metabolite DM003085
5391
Unclear 2 [3]
Oxazepam DM003073
4616
Oxidation - Hydroxylation 3 [3]
Oxazepam DM003073
4616
Oxidation - Demethylation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001325 Ketazolam Diazepam Oxidation - Degradation Unclear [3]
MR001328 Diazepam Nordazepam Unclear CYP2C19 [3], [4]
MR001329 Diazepam Temazepam Unclear CYP3A4 [3]
MR001327 Nordazepam Oxazepam Oxidation - Hydroxylation Unclear [3]
MR001326 Temazepam Oxazepam Oxidation - Demethylation Unclear [3]
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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 National Center for Advancing Translational Science-Inxight: drug (92A214MD7Y)
2 Metabolic profile of oxazepam and related benzodiazepines: clinical and forensic aspects. Drug Metab Rev. 2017 Nov;49(4):451-463.
3 Urinary diazepam metabolite distribution in a chronic pain population J Anal Toxicol. 2014 Apr;38(3):135-42. doi: 10.1093/jat/bku001.
4 Pharmacokinetics of Diazepam and Its Metabolites in Urine of Chinese Participants. Drugs R D. 2022 Mar;22(1):43-50. doi: 10.1007/s40268-021-00375-y.

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