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

General Information of Drug (ID: DR1735)
Drug Name
Zolpidem tartrate
Synonyms
Zolpidem [INN:BAN]; Zolpidemum; Zolpidemum [Latin]; Zolpidem; 7K383OQI23; 82626-48-0; CHEBI:10125; CHEMBL911; DEA No. 2783; Lorex; N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine-3-acetamide; N,N,6-Trimethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetamide; N,N,6-Trimethyl-2-p-tolylimidazo[1,2-a]pyridine-3-acetamide; N,N-Dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide; NCGC00095179-01; SL-800750; UNII-7K383OQI23; ZAFYATHCZYHLPB-UHFFFAOYSA-N; 2,3-bis(oxidanyl)butanedioic acid; 99294-93-6; A845992; ACT03353; AK126641; AKOS016013007; AX8157421; BCP28445; CCG-100938; CHEMBL1723343; CPD000469145; HMS2051H09; HMS2232G04; HMS3374C07; HMS3393H09; Intermezzo; MLS001401453; N,N-Dimethyl-2-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)acetamide 2,3-dihydroxysuccinate; N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]ethanamide; NC00188; NYVVVBWEVRSKIU-UHFFFAOYSA-N; SAM001246549; SCHEMBL40721; SMR000469145
Indication Insomnia [ICD11: 7A00] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 457.5 Topological Polar Surface Area 153
Heavy Atom Count 33 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
18004026
CAS Number
99294-93-6
TTD Drug ID
D0T1WN
Formula
C23H27N3O7
Canonical SMILES
CC1=CC=C(C=C1)C2=C(N3C=C(C=CC3=N2)C)CC(=O)N(C)C.C(C(C(=O)O)O)(C(=O)O)O
InChI
1S/C19H21N3O.C4H6O6/c1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19;5-1(3(7)8)2(6)4(9)10/h5-10,12H,11H2,1-4H3;1-2,5-6H,(H,7,8)(H,9,10)
InChIKey
NYVVVBWEVRSKIU-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
7-Hydroxy zolpidem DM005371
131801074
Oxidation - Aliphatic hydroxylation 1 [9]
8-Hydroxy zolpidem DM005372 N. A. Oxidation - Aliphatic hydroxylation 1 [9]
Methoxyzolpidem DM005373
154699860
Oxidation - Aliphatic hydroxylation 1 [10] , [11]
Methoxyzolpidem derivative (M3) DM005367
13691335
Oxidation - Methyl-hydroxylation 1 [10] , [11]
Methoxyzolpidem derivative (M4) DM005369
13691337
Oxidation - Methyl-hydroxylation; oxidation 1 [10] , [11]
Zolpidem carboxylic acid derivative (M1) DM005368
11966044
Oxidation - Oxidationn 2 [10] , [11]
Zolpidem carboxylic acid derivative (M2) DM005370
13691338
Oxidation - Oxidationn 2 [10] , [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005696 Zolpidem tartrate Methoxyzolpidem derivative (M3) Oxidation - Methyl-hydroxylation CYP2C9 ... [10], [11]
MR005698 Zolpidem tartrate Methoxyzolpidem derivative (M4) Oxidation - Methyl-hydroxylation; oxidation CYP3A4 ... [10], [11]
MR005700 Zolpidem tartrate 7-Hydroxy zolpidem Oxidation - Aliphatic hydroxylation CYP3A4 [9]
MR005701 Zolpidem tartrate 8-Hydroxy zolpidem Oxidation - Aliphatic hydroxylation CYP3A4 [9]
MR005702 Zolpidem tartrate Methoxyzolpidem Oxidation - Aliphatic hydroxylation CYP2C9 ... [10], [11]
MR005697 Methoxyzolpidem derivative (M3) Zolpidem carboxylic acid derivative (M1) Oxidation - Oxidationn Unclear [10], [11]
MR005699 Methoxyzolpidem derivative (M4) Zolpidem carboxylic acid derivative (M2) Oxidation - Oxidationn Unclear [10], [11]
⏷ 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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[7]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[8]
⏷ Show the Full List of 7  DME(s)
References
1 Zolpidem Tartrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Adverse reactions to zolpidem: case reports and a review of the literature. Prim Care Companion J Clin Psychiatry. 2010;12(6). pii: PCC.09r00849.
3 The influences of CYP2C9*1/*3 genotype on the pharmacokinetics of zolpidem. Arch Pharm Res. 2018 Sep;41(9):931-936.
4 Effect of zolpidem on human cytochrome P450 activity, and on transport mediated by P-glycoprotein. Biopharm Drug Dispos. 2002 Dec;23(9):361-7.
5 Zolpidem pharmacokinetics and pharmacodynamics in metabolic interactions involving CYP3A: sex as a differentiating factor. Eur J Clin Pharmacol. 2010 Sep;66(9):955.
6 PharmGKB: A worldwide resource for pharmacogenomic information. Wiley Interdiscip Rev Syst Biol Med. 2018 Jul;10(4):e1417. (ID: PA166170041)
7 Principles of Clinical Pharmacology (Third Edition). 2012, Pages 417-436
8 Zolpidem extended-release: a single insomnia treatment option for sleep induction and sleep maintenance symptoms. Am J Ther. 2007 May-Jun;14(3):299-305.
9 Qualitative analysis of 7- and 8-hydroxyzolpidem and discovery of novel zolpidem metabolites in postmortem urine using liquid chromatography-tandem mass spectrometry
10 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.
11 Zolpidem urine excretion profiles and cross-reactivity with ELISA(?) kits in subjects using Zolpidem or Ambien(?) CR as a prescription sleep aid

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