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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-10-17 09:08:24 UTC |
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Update Date | 2020-02-26 21:25:41 UTC |
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HMDB ID | HMDB0005023 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Zolpidem |
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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. |
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Structure | |
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Synonyms | Value | Source |
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N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine-3-acetamide | ChEBI | Zolpidemum | ChEBI | Sanval | Kegg | Ambien | HMDB | Hypnogen | HMDB | Myslee | HMDB | Stilnoct | HMDB | Stilnox | HMDB | Zolpidem ambien | HMDB | Zolpidem tartrate | HMDB | Bikalm | HMDB | Zolpidem 1a pharma | HMDB | N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2a)pyridine-3-acetamide hemitartrate | HMDB | Zolpidem abz | HMDB | Amsic | HMDB | Dalparan | HMDB | Zolpinox | HMDB | Zodormdura | HMDB | Zoldem | HMDB | Zolirin | HMDB | Zolpi-lich | HMDB | Zolpimist | HMDB | Zolpidem hemitartrate | MeSH | Zolpi lich | MeSH |
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Chemical Formula | C19H21N3O |
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Average Molecular Weight | 307.3895 |
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Monoisotopic Molecular Weight | 307.168462309 |
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IUPAC Name | N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide |
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Traditional Name | zolpidem |
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CAS Registry Number | 82626-48-0 |
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SMILES | CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1 |
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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 |
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InChI Key | ZAFYATHCZYHLPB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azoles |
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Sub Class | Imidazoles |
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Direct Parent | Phenylimidazoles |
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Alternative Parents | |
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Substituents | - 5-phenylimidazole
- 4-phenylimidazole
- Imidazopyridine
- Imidazo[1,2-a]pyridine
- Toluene
- Methylpyridine
- Monocyclic benzene moiety
- N-substituted imidazole
- Pyridine
- Benzenoid
- Tertiary carboxylic acid amide
- Heteroaromatic compound
- Carboxamide group
- Carboxylic acid derivative
- Azacycle
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 196 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-007c-4491000000-1f69c88ada0cbe422976 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4r-0196000000-6304f5b37ed9f071eb26 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0049000000-bc33df0258d99c887a5c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0bti-0095000000-53d24c4b41c278d039e0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052r-1190000000-fcb2a47c2fab91af9648 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0009000000-ad3531d27ad6da8d9cc3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bt9-1097000000-084e5a788c15061e05a5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-08fs-2090000000-b2e3eaa1af64958efe10 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-000i-1090000000-5429f5620534a2340098 | Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00425 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023594 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 5530 |
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KEGG Compound ID | C07219 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Zolpidem |
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METLIN ID | 3071 |
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PubChem Compound | 5732 |
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PDB ID | Not Available |
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ChEBI ID | 10125 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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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 |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- 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 ]
- 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 ]
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