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Record Information
Version3.6
Creation Date2006-10-17 09:08:24 UTC
Update Date2013-05-06 22:26:10 UTC
HMDB IDHMDB05023
Secondary Accession NumbersNone
Metabolite Identification
Common NameZolpidem
DescriptionZolpidem (sold under the brand names Ambien, Ambien CR, Stilnox, and Sublinox) is a prescription medication used for the treatment of insomnia, as well as some brain disorders. It is a short-acting nonbenzodiazepine hypnotic of the imidazopyridine class that potentiates gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, by binding to GABAA receptors at the same location as benzodiazepines. It works quickly (usually within 15 minutes) and has a short half-life (two to three hours). Zolpidem has not adequately demonstrated effectiveness in maintaining sleep (unless delivered in a controlled-release form); however, it is effective in initiating sleep. Some users take zolpidem recreationally for these side effects. However, it may be less common than benzodiazepine abuse. Zolpidem can become addictive if taken for extended periods of time, due to dependence on its ability to put one to sleep or to the euphoria it can sometimes produce.
Structure
Thumb
Synonyms
  1. Ambien
  2. Hypnogen
  3. Myslee
  4. Stilnoct
  5. Stilnox
  6. Zolpidem Ambien
  7. Zolpidem tartrate
Chemical FormulaC19H21N3O
Average Molecular Weight307.3895
Monoisotopic Molecular Weight307.168462309
IUPAC NameN,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide
Traditional IUPAC Namezolpidem
CAS Registry Number82626-48-0
SMILES
CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C19H21N3O/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/h5-10,12H,11H2,1-4H3
InChI KeyZAFYATHCZYHLPB-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassImidazopyridines
Sub ClassN/A
Other Descriptors
  • imidazopyridine(ChEBI)
Substituents
  • Carboxamide Group
  • Imidazole
  • Pyridine
  • Tertiary Carboxylic Acid Amide
  • Toluene
Direct ParentImidazopyridines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point196 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.031 g/LALOGPS
logP3.15ALOGPS
logP3.02ChemAxon
logS-4ALOGPS
pKa (strongest basic)5.65ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area37.61ChemAxon
rotatable bond count3ChemAxon
refractivity93.58ChemAxon
polarizability35.64ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Liver
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023594
KNApSAcK IDNot Available
Chemspider ID5530
KEGG Compound IDC07219
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZolpidem
NuGOwiki LinkHMDB05023
Metagene LinkHMDB05023
METLIN ID3071
PubChem Compound5732
PDB IDNot Available
ChEBI ID10125
References
Synthesis ReferenceKaplan, Jean Pierre; George, Pascal. Imidazo[1,2-a]pyridine derivatives and their therapeutic use. Eur. Pat. Appl. (1982), 19 pp. CODEN: EPXXDW EP 50563 A1 19820428 CAN 97:92280 AN 1982:492280
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Gock SB, Wong SH, Nuwayhid N, Venuti SE, Kelley PD, Teggatz JR, Jentzen JM: Acute zolpidem overdose--report of two cases. J Anal Toxicol. 1999 Oct;23(6):559-62. Pubmed: 10517569
  2. Von Moltke LL, Greenblatt DJ, Granda BW, Duan SX, Grassi JM, Venkatakrishnan K, Harmatz JS, Shader RI: Zolpidem metabolism in vitro: responsible cytochromes, chemical inhibitors, and in vivo correlations. Br J Clin Pharmacol. 1999 Jul;48(1):89-97. Pubmed: 10383565
  3. von Moltke LL, Weemhoff JL, Perloff MD, Hesse LM, Harmatz JS, Roth-Schechter BF, Greenblatt DJ: Effect of zolpidem on human cytochrome P450 activity, and on transport mediated by P-glycoprotein. Biopharm Drug Dispos. 2002 Dec;23(9):361-7. Pubmed: 12469329

Enzymes

General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Converts adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS) and 3'(2')-phosphoadenosine 5'- phosphate (PAP) to AMP. Has 1000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2) and inositol 1,3,4-trisphosphate (Ins(1,3,4)P3), but does not hydrolyze Ins(1)P, Ins(3,4)P2, Ins(1,3,4,5)P4 or InsP6.
Gene Name:
BPNT1
Uniprot ID:
O95861
Molecular weight:
33392.035
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
Gene Name:
TALDO1
Uniprot ID:
P37837
Molecular weight:
37539.74
General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in protein domain specific binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathway. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner
Gene Name:
YWHAZ
Uniprot ID:
P63104
Molecular weight:
27744.8
General function:
Signal transduction mechanisms
Specific function:
Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme. Plays a role in the transport of cholesterol across mitochondrial membranes in steroidogenic cells
Gene Name:
TSPO
Uniprot ID:
P30536
Molecular weight:
18778.7
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
General function:
Involved in protein domain specific binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathway. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Negative regulator of osteogenesis
Gene Name:
YWHAB
Uniprot ID:
P31946
Molecular weight:
28082.2
General function:
Involved in protein domain specific binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathway. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner
Gene Name:
YWHAG
Uniprot ID:
P61981
Molecular weight:
28302.3