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

General Information of Drug (ID: DR1173)
Drug Name
Nordazepam
Synonyms
Calmday; Chlordesmethyldiazepam; Dealkylprazepam; Demadar; Demethyldiazepam; Desalkylprazepam; N-Demethyldiazepam; N-Deoxydemoxapam; N-Deoxydemoxepam; N-Descyclopropylmethylprazepam; N-Desmethyldiazepam; N1-Desmethyldiazepam; Nordaz; Nordazepam; Nordazepam [INN]; Nordazepamum; Nordazepamum [INN-Latin]; Nordiazepam; Norprazepam; Praxadium; Ro 5-2180; Stilny; Vegesan; desmethyldiazepam; 1-Demethyldiazepam; 1088-11-5; 7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one; A 101; A101; DMDZ; Lomax; Madar; NSC 46078; Sopax
Indication Anxiety disorder [ICD11: 6B00] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 270.71 Topological Polar Surface Area 41.5
Heavy Atom Count 19 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2997
ChEBI ID
CHEBI:111762
CAS Number
1088-11-5
Formula
C15H11ClN2O
Canonical SMILES
C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3
InChI
1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)
InChIKey
AKPLHCDWDRPJGD-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
Oxazepam DM003073
4616
Oxidation - C3-hydroxylation 1 [4] , [5]
Oxazepam glucuronides DM004046
91800020
Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004426 Nordazepam Oxazepam Oxidation - C3-hydroxylation Unclear [4], [5]
MR004427 Oxazepam Oxazepam glucuronides Unclear Unclear [5]
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 Preparation of a novel sorptive stir bar based on vinylpyrrolidone-ethylene glycol dimethacrylate monolithic polymer for the simultaneous extraction of diazepam and nordazepam from human plasma. J Sep Sci. 2016 Apr;39(7):1316-25.
2 Sigmoidal kinetic model for two co-operative substrate-binding sites in a cytochrome P450 3A4 active site: an example of the metabolism of diazepam and its derivatives. Biochem J. 1999 Jun 15;340 ( Pt 3):845-53.
3 Effect of the gene dosage of CgammaP2C19 on diazepam metabolism in Chinese subjects. Clin Pharmacol Ther. 1999 Dec;66(6):642-6.
4 Kinetics of sequential metabolism. I. Formation and metabolism of oxazepam from nordiazepam and temazepam in the perfused murine liver
5 Kinetics of sequential metabolism. II. Formation and metabolism of nordiazepam and oxazepam from diazepam in the perfused murine liver

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