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

General Information of Drug (ID: DR0480)
Drug Name
Diazepam
Synonyms
Diacepan; Diapam; Diazemuls; Diazepan; Diazetard; Dipezona; Domalium; Faustan; Kiatrium; Levium; Liberetas; Methyldiazepinone; Neurolytril; Paranten; Quetinil; Quiatril; Quievita; Relaminal; Relanium; Renborin; Ruhsitus; Sedipam; Seduksen; Amiprol; Ansiolin; Ansiolisina; Apaurin; Apozepam; Assival; Atensine; Atilen; Bensedin; Bialzepam; Calmocitene; Calmpose; Ceregulart; Condition; Seduxen; Serenack; Serenamin; Serenzin; Sibazon; Sonacon; Stesolid; Stesolin; Tensopam; Tranimul; Tranqdyn; Tranquirit; Umbrium; Unisedil; Valitran; Valium; diazepam; 439-14-5
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 284.74 Topological Polar Surface Area 32.7
Heavy Atom Count 20 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3016
PubChem SID
9163 ; 118340 ; 442487 ; 589069 ; 597369 ; 866565 ; 3248698 ; 5349992 ; 7847359 ; 7849643 ; 7887249 ; 7945393 ; 7979063 ; 8027939 ; 8150113 ; 8151919 ; 10522913 ; 11336142 ; 11361381 ; 11372878 ; 11374151 ; 11462353 ; 11491595 ; 11492391 ; 14799843 ; 24893306 ; 24894120 ; 26719642 ; 29222163 ; 46386554 ; 46505210 ; 47440353 ; 47515391 ; 47662377 ; 48259330 ; 48413548 ; 48415873 ; 48423248 ; 49742658 ; 49854346 ; 50122777 ; 50660483 ; 53788455 ; 56313613 ; 57321555 ; 57654125 ; 81041007 ; 85788516 ; 85856297 ; 92308494
ChEBI ID
CHEBI:49575
CAS Number
439-14-5
TTD Drug ID
D07JVL
Formula
C16H13ClN2O
Canonical SMILES
CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3
InChI
1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
InChIKey
AAOVKJBEBIDNHE-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
Desmethyldiazepam DM000834
2997
Unclear 1 [12] , [13]
Desmethyldiazepam DM000834
2997
Oxidation - N-Demethylation 1 [14] , [13] , [15]
Medazepam metabolite DM003085
5391
Oxidation - 3-Hydroxylation 1 [12] , [13] , [15]
Oxazepam DM003073
4616
Oxidation - N-Demethylation 1 [12] , [13] , [15]
Nordiazepam O-glucuronide DM000832 N. A. Conjugation - O-Glucuronidation 2 [14]
Oxazepam DM003073
4616
Oxidation - N-Demethylation 2 [12] , [15]
Oxazepam DM003073
4616
Unclear 2 [14] , [13] , [15]
Temazepam O-glucuronide DM000833 N. A. Conjugation - O-Glucuronidation 2 [12] , [13]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000819 Diazepam Desmethyldiazepam Unclear Unclear [12], [13]
MR000820 Diazepam Oxazepam Oxidation - N-Demethylation CYP1A2 [12], [13], [15]
MR000821 Diazepam Temazepam Oxidation - 3-Hydroxylation PTGS1 ... [12], [13], [15]
MR000824 Nordazepam Nordiazepam O-glucuronide Conjugation - O-Glucuronidation Unclear [14]
MR000825 Nordazepam Oxazepam Unclear CYP2C19 ... [14], [13], [15]
MR000822 Temazepam Temazepam O-glucuronide Conjugation - O-Glucuronidation Unclear [12], [13]
MR000823 Temazepam Oxazepam Oxidation - N-Demethylation CYP2C9 ... [12], [15]
⏷ Show the Full List of 7 MR(s)
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]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[8]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[9]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[10]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[11]
⏷ Show the Full List of 10  DME(s)
References
1 Diazepam was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro metabolism of zolmitriptan in rat cytochromes induced with beta-naphthoflavone and the interaction between six drugs and zolmitriptan. Chem Biol Interact. 2003 Dec 15;146(3):263-72.
3 Inhibitory monoclonal antibody to human cytochrome P450 2B6. Biochem Pharmacol. 1998 May 15;55(10):1633-40.
4 Targeted antipeptide antibodies to cytochrome P450 2C18 based on epitope mapping of an inhibitory monoclonal antibody to P450 2C51. Arch Biochem Biophys. 1997 Feb 15;338(2):157-64.
5 Use of inhibitory monoclonal antibodies to assess the contribution of cytochromes P450 to human drug metabolism. Eur J Pharmacol. 2000 Apr 14;394(2-3):199-209.
6 Phenytoin-diazepam interaction. Ann Pharmacother. 2003 May;37(5):659-63.
7 Comparative study of the metabolism of drug substrates by human cytochrome P450 3A4 expressed in bacterial, yeast and human lymphoblastoid cells. Xenobiotica. 2002 Nov;32(11):937-47.
8 Eight inhibitory monoclonal antibodies define the role of individual P-450s in human liver microsomal diazepam, 7-ethoxycoumarin, and imipramine metabolism. Drug Metab Dispos. 1999 Jan;27(1):102-9.
9 Drug Interactions Flockhart Table
10 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
11 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
12 DrugBank(Pharmacology-Metabolism)Diazepam
13 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.
14 Study on the Pharmacokinetics of Diazepam and Its Metabolites in Blood of Chinese People Eur J Drug Metab Pharmacokinet. 2020 Aug;45(4):477-485. doi: 10.1007/s13318-020-00614-8.
15 Kinetic disposition of diazepam and its metabolites after intravenous administration of diazepam in the horse: Relevance for doping control. J Vet Pharmacol Ther. 2021 Sep;44(5):733-744. doi: 10.1111/jvp.12991.

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