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

General Information of Drug (ID: DR1547)
Drug Name
Temazepam
Synonyms
Temador; Temazepamum; Temazepamum [INN-Latin]; Temtabs; Uvamin Retard; WY 3917; Wy-3917; temazep von ct; temazepam; 3-Hydroxydiazepam; Cerepax; Crisonar; Dasuen; ER 115; Euhypnos; Euipnos; Gelthix; Hydroxydiazepam; K-3917; Levanxene; Levanxol; Levanzene; Mabertin; Methyloxazepam; N-Methyloxazepam; Neodorm SP; Nocturne; Nomapam; Norkotral Tema; Normison; Normitab; Nortem; Oxydiazepam; Perdorm; Planum; Pronervon T; Remestan; Restoril; Ro 5-5345; Signopam; 846-50-4; Lenal; Temaz; Tenox
Indication Insomnia [ICD11: 7A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 300.74 Topological Polar Surface Area 52.9
Heavy Atom Count 21 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5391
PubChem SID
9335 ; 136538 ; 3249168 ; 4624912 ; 7847436 ; 7980739 ; 8150144 ; 8153314 ; 10536883 ; 11336164 ; 11361403 ; 11462375 ; 14873813 ; 24900518 ; 29215382 ; 29224443 ; 46506604 ; 47216853 ; 48414499 ; 48416596 ; 49857686 ; 50335785 ; 57322751 ; 57654708 ; 92729793 ; 99302077 ; 103252229 ; 104309107 ; 124892195 ; 126674763 ; 129225114 ; 134337552 ; 134979721 ; 136949648 ; 137128143 ; 143325958 ; 144205223 ; 144207242 ; 160963579 ; 163357056 ; 164765243 ; 175611282 ; 176262034 ; 178103873 ; 179116909 ; 198991797 ; 223441048 ; 223682944 ; 224807633 ; 226416533
ChEBI ID
CHEBI:9435
CAS Number
846-50-4
TTD Drug ID
D04BNP
Formula
C16H13ClN2O2
Canonical SMILES
CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)O)C3=CC=CC=C3
InChI
1S/C16H13ClN2O2/c1-19-13-8-7-11(17)9-12(13)14(18-15(20)16(19)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3
InChIKey
SEQDDYPDSLOBDC-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
O-conjugate of temazepam DM000483 N. A. Conjugation - Conjugation 1 [6]
Oxazepam DM003073
4616
Oxidation - Demethylation 1 [5] , [6]
Temazepam metabolite M1 DM000482 N. A. Oxidation - Demethylation 2 [6] , [2]
Temazepam metabolite M1 DM000482 N. A. Conjugation - Conjugation 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002377 Temazepam O-conjugate of temazepam Conjugation - Conjugation Unclear [6]
MR002378 Temazepam Oxazepam Oxidation - Demethylation CYP3A4(major) ... [5], [6]
MR002376 O-conjugate of temazepam Temazepam metabolite M1 Oxidation - Demethylation CYP3A4(major) ... [6], [2]
MR002379 Oxazepam Temazepam metabolite M1 Conjugation - Conjugation Unclear [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
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
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
⏷ Show the Full List of 6  DME(s)
References
1 Temazepam was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
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 Role of cDNA-expressed human cytochromes P450 in the metabolism of diazepam. Biochem Pharmacol. 1998 Mar 15;55(6):889-96.
4 Human liver microsomal diazepam metabolism using cDNA-expressed cytochrome P450s: role of CYP2B6, 2C19 and the 3A subfamily Xenobiotica. 1996 Nov;26(11):1155-66. doi: 10.3109/00498259609050260.
5 Human liver microsomal diazepam metabolism using cDNA-expressed cytochrome P450s: role of CYP2B6, 2C19 and the 3A subfamily. Xenobiotica. 1996 Nov;26(11):1155-66.
6 Pharmacokinetics and metabolism of temazepam in man and several animal species Br J Clin Pharmacol. 1979;8(1):23S-29S. doi: 10.1111/j.1365-2125.1979.tb00451.x.

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