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

General Information of Drug (ID: DR1214)
Drug Name
Oxazepam
Synonyms
Oxanid; Oxazepamum; Oxozepam; Pacienx; Praxiten; Propax; Psicopax; Psiquiwas; Quilibrex; Rondar; Sedigoa; Serenal; Serenid; Serenid-D; Serepax; Seresta; Serpax; Sigacalm; Sobril; Tacepam; Tarchomin; Tazepam; Tranquo-buscopan-wirkstoff; Zaxopam; Adumbran; Alepam; Ansioxacepam; Anxiolit; Anxiolit retard; Aplakil; Astress; Azutranquil; Bonare; Drimuel; Droxacepam; Durazepam; Hi-Long; Isodin; Lederpam; Limbial; Murelax; Nesontil; Noctazepam; Nortemazepam; Nozepam; Oxa-puren; oxazepam; (+-)-Oxazepam; (RS)-Oxazepam; 604-75-1; Abboxapam; QUEN; Serax; Uskan; Vaben
Indication Anxiety disorder [ICD11: 6B00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 286.71 Topological Polar Surface Area 61.7
Heavy Atom Count 20 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4616
PubChem SID
9563 ; 442236 ; 3249122 ; 5195891 ; 7847530 ; 7849644 ; 7980215 ; 8145938 ; 8150141 ; 8152833 ; 10529275 ; 11336161 ; 11361400 ; 11462372 ; 14848993 ; 24898014 ; 29215230 ; 29223705 ; 46506031 ; 47515395 ; 47959852 ; 48414263 ; 48416359 ; 48423875 ; 49854270 ; 49884181 ; 50775696 ; 53787011 ; 56311180 ; 57322352 ; 87689980 ; 99233239 ; 99302074 ; 103179009 ; 104306922 ; 124892098 ; 124892099 ; 125824328 ; 126671574 ; 127390117 ; 134337557 ; 134977280 ; 135343430 ; 136351131 ; 137089237 ; 137203466 ; 137261518 ; 140053015 ; 144205125 ; 144206372
ChEBI ID
ChEBI:7823
CAS Number
604-75-1
TTD Drug ID
D09LDR
Formula
C15H11ClN2O2
Canonical SMILES
C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)O
InChI
1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)
InChIKey
ADIMAYPTOBDMTL-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 glucuronide DM001106
160870
Conjugation - O-Glucuronidation 1 [6]
Unclear DM009999 N. A. Oxidation - Deamination 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002862 Oxazepam Oxazepam glucuronide Conjugation - O-Glucuronidation UGT1A9 ... [6]
MR002863 Oxazepam . Oxidation - Deamination CYP3A4 [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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[6]
⏷ Show the Full List of 7  DME(s)
References
1 Oxazepam was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Bioreactor systems in drug metabolism: synthesis of cytochrome P450-generated metabolites. Metab Eng. 2000 Apr;2(2):115-25.
3 Cytochrome P450 enzyme activity and protein expression in primary porcine enterocyte and hepatocyte cultures. Xenobiotica. 2000 Jan;30(1):27-46.
4 Evidence for oxazepam as an in vivo probe of UGT2B15: oxazepam clearance is reduced by UGT2B15 D85Y polymorphism but unaffected by UGT2B17 deletion. Br J Clin Pharmacol. 2009 Nov;68(5):721-30.
5 Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9 Drug Metab Dispos. 2002 Nov;30(11):1257-65. doi: 10.1124/dmd.30.11.1257.
6 Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab Dispos. 2002 Nov;30(11):1257-65.

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