Zolpidem (CED0002968)

Record Information
Version1.0
Creation Date2009-07-21 20:26:52 UTC
Update Date2026-05-14 16:38:23 UTC
Accession NumberCHEM002192
Identification
Common NameZolpidem
ClassSmall Molecule
Description
Zolpidem is an exogenous organic compound with the formula C19H21N3O and an average molecular weight of 307.39 g/mol. It exists as a solid at room temperature. Zolpidem belongs to the imidazoles, a subclass of azoles within the organic compounds. Used as a sedative and central nervous system depressant, zolpidem functions biologically as a GABA agonist. It interacts with nine recorded protein targets, including the translocator protein (TSPO) and several subunits of the gamma-aminobutyric acid receptor, such as GABRB3 and GABRA2, GABRA3, and GABRA4. Specifically, zolpidem modulates the alpha-subunit within the GABAA receptor chloride channel macromolecular complex; unlike benzodiazepines that interact non-selectively with all three alpha-receptor subtypes, zolpidem preferentially binds to the alpha-1 receptor (GABRA1). The compound is found in healthcare, pharmaceuticals, and veterinary products as a hypnotic and sedative. It has been detected in the liver and is associated with oral and sublingual exposure routes. Additionally, zolpidem has been recorded in 20 sources, including drinking water, floors, various household cleaning and consumer products—such as perfumes within detergents and soaps, cigar cigarettes, and pipe accessories—as well as food preservation and the treatment of hops. It is also found in electrical and electronic equipment, including electrodes, fixed capacitors, electric switches, and electrically stimulated smoking devices.
Contaminant Type
  • Amide
  • Amine
  • Drug
  • Food Toxin
  • GABA Agonist
  • GABA-A Receptor Agonist
  • Human Neurotoxin
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine-3-acetamideChEBI
ZolpidemumChEBI
SanvalKegg
AmbienHMDB
HypnogenHMDB
MysleeHMDB
StilnoctHMDB
StilnoxHMDB
Zolpidem ambienHMDB
Zolpidem tartrateHMDB
BikalmHMDB
Zolpidem 1a pharmaHMDB
N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2a)pyridine-3-acetamide hemitartrateHMDB
Zolpidem abzHMDB
AmsicHMDB
DalparanHMDB
ZolpinoxHMDB
ZodormduraHMDB
ZoldemHMDB
ZolirinHMDB
Zolpi-lichHMDB
ZolpimistHMDB
Zolpidem hemitartrateHMDB
Zolpi lichHMDB
Chemical FormulaC19H21N3O
Average Molecular Mass307.390 g/mol
Monoisotopic Mass307.168 g/mol
CAS Registry Number82626-48-0
IUPAC NameN,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide
Traditional Namezolpidem
SMILESCN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1
InChI IdentifierInChI=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
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentPhenylimidazoles
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Liver
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point196°C
Boiling PointNot Available
Solubility23 mg/mL
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 Area37.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.58 m³·mol⁻¹ChemAxon
Polarizability35.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-007c-4491000000-1f69c88ada0cbe422976Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4r-0196000000-6304f5b37ed9f071eb26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-06ri-0093000000-df20eb1ec18c6314769fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0049000000-bc33df0258d99c887a5cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bti-0095000000-53d24c4b41c278d039e0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-1190000000-fcb2a47c2fab91af9648Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-ad3531d27ad6da8d9cc3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-1097000000-084e5a788c15061e05a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fs-2090000000-b2e3eaa1af64958efe10Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-de69c65803e567e26ceaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-074i-0093000000-612afe202f557c4a4c66Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0490000000-26b5c78b7009ce2e5c1cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0019000000-b660ca11ad7e4f91fd36Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-0092000000-37a7218a24afef1be815Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0390000000-fe5078d60002f0380d8eNot AvailableView Spectrum
MSMS Spectrumsplash10-000i-1090000000-5429f5620534a2340098Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityZolpidem modulates the alpha-subunit, known as the benzodiazepine receptor, within the GABAA receptor chloride channel macromolecular complex. Unlike the benzodiazepines, which non-selectively interact with all three alpha-receptor subtypes, Zolpidem preferentially binds to the alpha-1 receptor.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms of overdose include impairment of consciousness ranging from somnolence to light coma.
TreatmentGeneral symptomatic and supportive measures should be used along with immediate gastric lavage where appropriate. Intravenous fluids should be administered as needed. sedative hypnotic effect was shown to be reduced by flumazenil and therefore may be useful; however, flumazenil administration may contribute to the appearance of neurological symptoms (convulsions). As in all cases of drug overdose, respiration, pulse, blood pressure, and other appropriate signs should be monitored and general supportive measures employed. Hypotension and CNS depression should be monitored and treated by appropriate medical intervention. Sedating drugs should be withheld following zolpidem overdosage, even if excitation occurs. The value of dialysis in the treatment of overdosage has not been determined, although hemodialysis studies in patients with renal failure receiving therapeutic doses have demonstrated that zolpidem is not dialyzable. (11)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
695.0mg/kgNot AvailableRatLD50OralexperimentalA308
944.0Log mg/kg[530:1700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
376Hypnotics and sedativesHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureTranslocator proteinP16257Rattus norvegicusPredicted (SEA)0.544945
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-3P20236Rattus norvegicusPredicted (SEA)0.0778492
Gamma-aminobutyric acid receptor subunit alpha-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-1P14867HumansPredicted (SEA)1.08989
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-5P19969Rattus norvegicusPredicted (SEA)0.155698
Gamma-aminobutyric acid receptor subunit alpha-5 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-5P31644HumansPredicted (SEA)2.02408
Gamma-aminobutyric acid receptor subunit alpha-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-2P47869HumansPredicted (SEA)0.544945
Gamma-aminobutyric acid receptor subunit alpha-3 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-3P34903HumansPredicted (SEA)0.700643
Click to view 3D structureTranslocator proteinP30536HumansPredicted (SEA)34.098
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-1P62813Rattus norvegicusPredicted (SEA)0.0778492
Solute carrier family 2, facilitated glucose transporter member 1 structureClick to view 3D structureSolute carrier family 2, facilitated glucose transporter member 1P11166HumansPredicted (SEA)75.9808
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-2P23576Rattus norvegicusPredicted (SEA)0.0778492
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)945.946
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)139.661
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)3548.68
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)3997.79
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)956.689
Click to view 3D structureCdc2-related kinaseO96526Leishmania majorPredicted (SEA)44.4519
Albumin structureClick to view 3D structureAlbuminP02768HumansPredicted (SEA)168.31
Click to view 3D structureSolute carrier family 2, facilitated glucose transporter member 2P11168HumansPredicted (SEA)3.03612
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)3308.36
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)5069.23
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)4313.7
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)2200.25
Click to view 3D structureGlutamate receptor ionotropic, NMDA 2BQ00960Rattus norvegicusPredicted (SEA)93.4969
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)3700.95
Gamma-aminobutyric acid receptor subunit alpha-3 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-3P34903HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit alpha-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-2P47869HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit beta-3 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-3P28472HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit alpha-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-1P14867HumansKnownZolpidem modulates the alpha-subunit, known as the benzodiazepine receptor, within the GABAA receptor chloride channel macromolecular complex. Unlike the benzodiazepines, which non-selectively interact with all three alpha-receptor subtypes, Zolpidem preferentially binds to the alpha-1 receptor.
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-6Q16445HumansKnownNot Available
Click to view 3D structureTranslocator proteinP30536HumansKnownZolpidem modulates the alpha-subunit, known as the benzodiazepine receptor, within the GABAA receptor chloride channel macromolecular complex. Unlike the benzodiazepines, which non-selectively interact with all three alpha-receptor subtypes, Zolpidem preferentially binds to the alpha-1 receptor.
Gamma-aminobutyric acid receptor subunit alpha-4 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-4P48169HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00425
HMDB IDHMDB0005023
FooDB IDFDB023594
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3071
PDB IDNot Available
Wikipedia LinkZolpidem
Chemspider ID5530
ChEBI ID10125
PubChem Compound ID5732
Kegg Compound IDC07219
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Markus Sauter, “Process for preparing zolpidem.” U.S. Patent US20020183522, issued December 05, 2002.

MSDSLink
General References
1. 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
2. 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
3. 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.
4. 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.
5. 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.