Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Zolpidem (HMDB05023)

Record Information
Version 3.5
Creation Date 2006-10-17 03:08:24 -0600
Update Date 2013-05-06 16:26:10 -0600
HMDB ID HMDB05023
Secondary Accession Numbers None
Metabolite Identification
Common Name Zolpidem
Description Zolpidem (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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Ambien
  2. Hypnogen
  3. Myslee
  4. Stilnoct
  5. Stilnox
  6. Zolpidem Ambien
  7. Zolpidem tartrate
Chemical Formula C19H21N3O
Average Molecular Weight 307.3895
Monoisotopic Molecular Weight 307.168462309
IUPAC Name N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide
Traditional IUPAC Name zolpidem
CAS Registry Number 82626-48-0
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 Key ZAFYATHCZYHLPB-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Imidazopyridines
Sub Class N/A
Other Descriptors
  • imidazopyridine(ChEBI)
Substituents
  • Carboxamide Group
  • Imidazole
  • Pyridine
  • Tertiary Carboxylic Acid Amide
  • Toluene
Direct Parent Imidazopyridines
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 196 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 3.15 ALOGPS
LogP 3.02 ChemAxon
LogS -3.99 ALOGPS
pKa (strongest basic) 5.65 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 37.61 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 93.58 ChemAxon
Polarizability 35.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location
  • Liver
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023594
KNApSAcK ID Not Available
Chemspider ID 5530 Link_out
KEGG Compound ID C07219 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Zolpidem Link_out
NuGOwiki Link HMDB05023 Link_out
Metagene Link HMDB05023 Link_out
METLIN ID 3071 Link_out
PubChem Compound 5732 Link_out
PDB ID Not Available
ChEBI ID 10125 Link_out
References
Synthesis Reference Kaplan, 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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: 3'(2'),5'-bisphosphate nucleotidase 1
Reactions:
  • adenosine 3',5'-bisphosphate + H2O = adenosine 5'-phosphate + phosphate [RN:R00188]
Gene Name: BPNT1
Uniprot ID: O95861 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transaldolase
Reactions:
  • sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate [RN:R08575]
Gene Name: TALDO1
Uniprot ID: P37837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoserine aminotransferase
Reactions:
  • (1) O-phospho-L-serine + 2-oxoglutarate = 3-phosphonooxypyruvate + L-glutamate [RN:R04173]
  • (2) 4-phosphonooxy-L-threonine + 2-oxoglutarate = (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + L-glutamate
Gene Name: PSAT1
Uniprot ID: Q9Y617 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions:
  • (1) taurochenodeoxycholate + NADPH + H+ + O2 = taurohyocholate + NADP+ + H2O [RN:R07205]
  • (2) lithocholate + NADPH + H+ + O2 = hyodeoxycholate + NADP+ + H2O [RN:R07206]
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 14-3-3 protein zeta/delta
Reactions:
    Gene Name: YWHAZ
    Uniprot ID: P63104 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Translocator protein
    Reactions:
      Gene Name: TSPO
      Uniprot ID: P30536 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Gamma-aminobutyric acid receptor subunit alpha-1
      Reactions:
        Gene Name: GABRA1
        Uniprot ID: P14867 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 14-3-3 protein beta/alpha
        Reactions:
          Gene Name: YWHAB
          Uniprot ID: P31946 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: 14-3-3 protein gamma
          Reactions:
            Gene Name: YWHAG
            Uniprot ID: P61981 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA