Identification

Name
Zolpidem
Accession Number
DB00425  (APRD00095)
Type
Small Molecule
Groups
Approved
Description

Zolpidem is a prescription short-acting nonbenzodiazepine hypnotic that potentiates gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, by binding to benzodiazepine receptors which are located on the gamma-aminobutyric acid receptors. Zolpidem is used for the short-term treatment of insomnia. It works quickly (usually within 15 minutes) and has a short half-life (2-3 hours). It is classified as an imidazopyridine. As an anticonvulsant and muscle relaxant, the beneficial effects start to emerge at 10 and 20 times the dose required for sedation, respectively. For that reason, it has never been approved for either muscle relaxation or seizure prevention. Recently, zolpidem has been cited in various medical reports mainly in the United Kingdom as waking persistent vegetative state (PVS) patients, and dramatically improving the conditions of people with brain injuries.

Structure
Thumb
Synonyms
  • N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine-3-acetamide
  • Zolpidem
  • Zolpidemum
External IDs
HSDB 7045 / SL 800750 / SL 800750-23N
Product Ingredients
IngredientUNIICASInChI Key
Zolpidem tartrateWY6W63843K99294-93-6VXRDAMSNTXUHFX-CEAXSRTFSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmbienTablet, film coated10 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2009-06-30Not applicableUs
AmbienTablet, film coated10 mg/1OralRebel Distributors2009-06-30Not applicableUs
AmbienTablet, film coated10 mg/1OralPhysicians Total Care, Inc.1995-02-162012-06-30Us
AmbienTablet, film coated5 mg/1Oralsanofi-aventis U.S. LLC1993-04-01Not applicableUs
AmbienTablet, film coated10 mg/1OralA S Medication Solutions1993-04-01Not applicableUs
AmbienTablet, film coated5 mg/1OralA-S Medication Solutions1993-04-012015-02-28Us
AmbienTablet, film coated10 mg/1OralCaremark L.L.C.2007-04-172011-12-31Us
AmbienTablet, film coated10 mg/1OralStat Rx USA1993-04-01Not applicableUs
AmbienTablet, film coated5 mg/1OralA S Medication Solutions1993-04-01Not applicableUs
AmbienTablet, film coated5 mg/1OralPhysicians Total Care, Inc.2000-07-262011-06-30Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmbienTablet5 mg/1OralDirectrx2016-02-10Not applicableUs
AmbienTablet10 mg/1OralDirectrx2016-01-28Not applicableUs
Apo-zolpidem ODTTablet, orally disintegrating10 mgSublingualApotex Corporation2015-02-13Not applicableCanada
Apo-zolpidem ODTTablet, orally disintegrating5 mgSublingualApotex Corporation2015-02-13Not applicableCanada
PMS-zolpidem ODTTablet, orally disintegrating5 mgSublingualPharmascience Inc2016-12-13Not applicableCanada
PMS-zolpidem ODTTablet, orally disintegrating10 mgSublingualPharmascience Inc2016-12-13Not applicableCanada
ZolpidemTablet5 mg/1OralWest Ward Pharmaceutical2008-04-30Not applicableUs
ZolpidemTablet10 mg/1OralWest Ward Pharmaceutical2008-04-30Not applicableUs
Zolpidem TartrateTablet, film coated, extended release12.5 mg/1OralAphena Pharma Solutions Tennessee, Inc.2010-12-06Not applicableUs
Zolpidem tartrateTablet, extended release12.5 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2011-10-31Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Gabazolpidem-5Zolpidem tartrate (5 mg/1) + Choline (125 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
Sentrazolpidem PM-5Zolpidem tartrate (5 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
International/Other Brands
Adormix (Sanofi Pasteur) / Bikalm (sanofi-aventis) / Dormizol (sanofi-aventis) / Hypnogen (Zentiva) / Ivedal (Winthrop) / Nasen (Polfarmex) / Nimadorm (Sandoz) / Nottem (sanofi-aventis) / Stilnoct (sanofi-aventis) / Stilnox (sanofi-aventis) / Stilnox CR (sanofi-aventis) / Zolsana (Krka) / Zoltis (Biofarm)
Categories
UNII
7K383OQI23
CAS number
82626-48-0
Weight
Average: 307.3895
Monoisotopic: 307.168462309
Chemical Formula
C19H21N3O
InChI Key
ZAFYATHCZYHLPB-UHFFFAOYSA-N
InChI
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
IUPAC Name
N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide
SMILES
CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1

Pharmacology

Indication

For the short-term treatment of insomnia.

Associated Conditions
Pharmacodynamics

Zolpidem is a sedative or hypnotic agent with a chemical structure unrelated to benzodiazepines, barbiturates, or other drugs with known hypnotic properties. It interacts with a GABA-BZ receptor complex and shares some of the pharmacological properties of the benzodiazepines. In contrast to the benzodiazepines, which non-selectively bind to and activate all three alpha receptor subtypes, zolpidem in vitro binds the (alpha1) receptor preferentially. The (alpha1) receptor is found primarily on the Lamina IV of the sensorimotor cortical regions, substantia nigra (pars reticulata), cerebellum molecular layer, olfactory bulb, ventral thalamic complex, pons, inferior colliculus, and globus pallidus.

Mechanism of action

Zolpidem 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.

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-1
potentiator
Human
UGamma-aminobutyric acid receptor subunit alpha-2
agonist
Human
UGamma-aminobutyric acid receptor subunit alpha-3
agonist
Human
UGamma-aminobutyric acid receptor subunit beta-3
agonist
Human
UGamma-aminobutyric acid receptor subunit gamma-2
agonist
Human
Absorption

Zolpidem is rapidly absorbed from the GI tract.

Volume of distribution
Not Available
Protein binding

92.5 ± 0.1% (independent of concentration between 40 and 790 ng/mL)

Metabolism

Zolpidem is converted to inactive metabolites in the liver.

Route of elimination

Zolpidem tartrate tablets are converted to inactive metabolites that are eliminated primarily by renal excretion.

Half life

2.6 hours

Clearance
Not Available
Toxicity

Oral (male rat) LD50 = 695 mg/kg. Symptoms of overdose include impairment of consciousness ranging from somnolence to light coma.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Zolpidem.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Zolpidem.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Zolpidem.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Zolpidem.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Zolpidem.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Zolpidem.
Food Interactions
  • Avoid alcohol.
  • Should not be administered with or immediately after a meal.

References

Synthesis Reference

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

US20020183522
General References
  1. Lemmer B: The sleep-wake cycle and sleeping pills. Physiol Behav. 2007 Feb 28;90(2-3):285-93. Epub 2006 Oct 16. [PubMed:17049955]
  2. Depoortere H, Zivkovic B, Lloyd KG, Sanger DJ, Perrault G, Langer SZ, Bartholini G: Zolpidem, a novel nonbenzodiazepine hypnotic. I. Neuropharmacological and behavioral effects. J Pharmacol Exp Ther. 1986 May;237(2):649-58. [PubMed:2871178]
  3. Clauss RP, Guldenpfennig WM, Nel HW, Sathekge MM, Venkannagari RR: Extraordinary arousal from semi-comatose state on zolpidem. A case report. S Afr Med J. 2000 Jan;90(1):68-72. [PubMed:10721397]
  4. Schlich D, L'Heritier C, Coquelin JP, Attali P, Kryrein HJ: Long-term treatment of insomnia with zolpidem: a multicentre general practitioner study of 107 patients. J Int Med Res. 1991 May-Jun;19(3):271-9. [PubMed:1670039]
  5. Maarek L, Cramer P, Attali P, Coquelin JP, Morselli PL: The safety and efficacy of zolpidem in insomniac patients: a long-term open study in general practice. J Int Med Res. 1992 Apr;20(2):162-70. [PubMed:1521672]
External Links
Human Metabolome Database
HMDB0005023
KEGG Compound
C07219
PubChem Compound
5732
PubChem Substance
46507949
ChemSpider
5530
BindingDB
26266
ChEBI
10125
ChEMBL
CHEMBL911
Therapeutic Targets Database
DAP000112
PharmGKB
PA451976
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Zolpidem
ATC Codes
N05CF02 — Zolpidem
AHFS Codes
  • 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics
FDA label
Download (323 KB)
MSDS
Download (170 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceDepression1
0Not Yet RecruitingTreatmentInsomnia Chronic1
0Unknown StatusBasic SciencePsychotropic Drugs Effects1
1CompletedNot AvailableAbuse Potential Study1
1CompletedNot AvailableHealthy Volunteers2
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Therapeutic Equivalency1
1CompletedBasic ScienceMarijuana Dependence1
1CompletedBasic ScienceMethodology Study1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentInsomnia Disorders1
1CompletedTreatmentSleep Initiation and Maintenance Disorders / Sleeplessness1
1CompletedTreatmentSleeplessness3
1RecruitingBasic ScienceProstatic Neoplasms1
1RecruitingTreatmentComplications, Arthroplasty / Perioperative/Postoperative Complications / Shoulder Arthritis / Sleep Disturbances1
1RecruitingTreatmentHealthy Recreational Drug Users1
1, 2CompletedTreatmentSleep Disorder / Sleeplessness1
2CompletedOtherInsomnia Disorder1
2CompletedTreatmentInsomnia Disorder1
2CompletedTreatmentPrimary Insomnia / Secondary Insomnia1
2CompletedTreatmentSleep Initiation and Maintenance Disorders1
2CompletedTreatmentMinor burns / Sleep1
2Not Yet RecruitingTreatmentParkinson's Disease (PD)1
2RecruitingTreatmentInsomnia Disorders1
2TerminatedTreatmentPrimary Insomnia1
2WithdrawnTreatmentParkinson's Disease (PD)1
2, 3Active Not RecruitingTreatmentPrimary Insomnia / Secondary Insomnia1
2, 3CompletedTreatmentPrimary Insomnia1
2, 3CompletedTreatmentSubstance, Addiction1
3CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
3CompletedTreatmentChild's Anxiety / Parental/Caregiver Anxiety1
3CompletedTreatmentPrimary Insomnia1
3CompletedTreatmentSleep Initiation and Maintenance Disorders2
3CompletedTreatmentSleep disorders and disturbances / Sleep Initiation and Maintenance Disorders1
3CompletedTreatmentSleeplessness3
3RecruitingTreatmentAlzheimer's Disease (AD) / Sleep / Sleep disorders and disturbances / Sleeplessness1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentSleeplessness1
4Active Not RecruitingTreatmentInsomnia Comorbid to Psychiatric Disorder / Primary Insomnia1
4CompletedNot AvailablePostural Instability1
4CompletedBasic ScienceMemory / Sleep1
4CompletedDiagnosticHealthy Volunteers1
4CompletedSupportive CareCognition / Pharmacologic Actions / Sleep1
4CompletedTreatmentDepression / Sleep Initiation and Maintenance Disorders2
4CompletedTreatmentDepression / Sleeplessness / Suicidal Thoughts1
4CompletedTreatmentInsomnia Chronic1
4CompletedTreatmentObstructive Sleep Apnea Syndrome (OSAS)1
4CompletedTreatmentPrimary Insomnia / Psychophysiologic Insomnia / Sleeplessness1
4CompletedTreatmentPrimary Insomnia / Sleep Initiation and Maintenance Disorders2
4CompletedTreatmentSleep Initiation and Maintenance Disorders1
4CompletedTreatmentSleep Initiation and Maintenance Disorders / Sleeplessness1
4CompletedTreatmentSleep disorders and disturbances3
4CompletedTreatmentSleeplessness6
4RecruitingBasic ScienceAging1
4RecruitingOtherPsychomotor Impairment1
4RecruitingTreatmentHeart Failure, Unspecified / Sleep Disturbances1
4TerminatedPreventionDelirium / Hip Fractures1
4Unknown StatusTreatmentPrimary Insomnia1
4WithdrawnBasic ScienceHealthy Volunteers1
Not AvailableCompletedNot AvailableHealthy Volunteers4
Not AvailableCompletedNot AvailablePrimary Insomnia1
Not AvailableCompletedBasic SciencePhysiology1
Not AvailableCompletedSupportive CareCancer, Breast / Menopausal Hot Flushes / Sleep disorders and disturbances1
Not AvailableCompletedTreatmentAging / Balance / Sleep1
Not AvailableCompletedTreatmentAlzheimer's Disease (AD) / Circadian Dysregulation / Dementia, Vascular / Dementias / Sleep disorders and disturbances1
Not AvailableCompletedTreatmentLiver Cirrhosis1
Not AvailableCompletedTreatmentPrimary Insomnia1
Not AvailableCompletedTreatmentSleep Initiation and Maintenance Disorders1
Not AvailableCompletedTreatmentSleeplessness2
Not AvailableRecruitingBasic ScienceSleeplessness1
Not AvailableTerminatedSupportive CareNeoplasms, Endometrial / Pain NOS / Sleep1
Not AvailableUnknown StatusNot AvailableOlder Adults1
Not AvailableUnknown StatusNot AvailableSleep Duration on the First Night After Surgery1

Pharmacoeconomics

Manufacturers
  • Novadel pharma inc
  • Sanofi aventis us llc
  • Biovail laboratories international srl
  • Apotex inc
  • Aurobindo pharma ltd
  • Caraco pharmaceutical laboratories ltd
  • Carlsbad technology inc
  • Dr reddys laboratories ltd
  • Genpharm inc
  • Hikma pharmaceuticals
  • Invagen pharmaceuticals inc
  • Lek pharmaceuticals dd
  • Mutual pharmacal co
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Synthon pharmaceuticals ltd
  • Teva pharmaceuticals usa inc
  • Torrent pharmaceuticals ltd
  • Vintage pharmaceuticals llc
  • Watson laboratories inc
  • Wockhardt ltd
  • World gen llc
  • Meda pharmaceuticals
  • Pfizer inc
Packagers
  • Actavis Group
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Bayer Healthcare
  • Bryant Ranch Prepack
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Caremark LLC
  • Carlsbad Technology Inc.
  • Chinoin Pharmaceutcial and Chemical Works Co. Ltd.
  • Corepharma LLC
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Dorx LLC
  • GD Searle LLC
  • Genpharm LP
  • Glenmark Generics Ltd.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Hikma Pharmaceuticals
  • Innoviant Pharmacy Inc.
  • InvaGen Pharmaceuticals Inc.
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Lek Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Meda AB
  • Metrics Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physician Therapeutics Inc. LLC
  • Physicians Total Care Inc.
  • Prasco Labs
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Roxane Labs
  • Sandoz
  • Sanofi-Aventis Inc.
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Synthon Pharmaceuticals Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Torrent Pharmaceuticals
  • UDL Laboratories
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
  • Yung Shin Pharmaceutical Industry Ltd.
Dosage forms
FormRouteStrength
Tablet, coatedOral12.5 mg/1
Tablet, coatedOral6.25 mg/1
Tablet, orally disintegratingSublingual10 mg
Tablet, orally disintegratingSublingual5 mg
TabletSublingual10 mg/1
TabletSublingual5 mg/1
Kit
TabletSublingual1.75 mg/1
TabletSublingual3.5 mg/1
TabletOral10 mg
TabletOral5 mg
KitOral
TabletOral10 mg/1
TabletOral5 mg/1
Tablet, coatedOral10 mg/1
Tablet, coatedOral5 mg/1
Tablet, extended releaseOral12.5 mg/1
Tablet, extended releaseOral6.25 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coated, extended releaseOral12.5 mg/1
Tablet, film coated, extended releaseOral6.25 mg/1
Spray, meteredOral5 mg/1
Prices
Unit descriptionCostUnit
Ambien cr 12.5 mg tablet6.19USD tablet
Ambien cr 6.25 mg tablet6.19USD tablet
Ambien 10 mg tablet6.11USD tablet
Ambien 5 mg tablet6.04USD tablet
Ambien CR 12.5 mg Controlled Release Tabs6.0USD tab
Ambien CR 6.25 mg Controlled Release Tabs6.0USD tab
Edluar 10 mg sl tablet5.0USD tablet
Edluar 5 mg sl tablet5.0USD tablet
Zolpidem tartrate 10 mg tablet2.73USD tablet
Zolpidem tartrate 5 mg tablet2.73USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6761910No2004-07-132019-09-24Us
US8512747No2013-08-202019-09-24Us
US9265720No2016-02-232030-05-13Us
US6514531Yes2003-02-042020-06-01Us
US7632517No2009-12-152017-10-01Us
US7658945No2010-02-092027-04-15Us
US7682628No2010-03-232025-02-16Us
US8242131No2012-08-142029-08-20Us
US8252809No2012-08-282025-02-16Us
US9597281No2017-03-212027-04-06Us
US8236285No2012-08-072032-08-07Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)196 °CPhysProp
water solubility23 mg/mLNot Available
logP1.2Not Available
pKa6.2MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.0313 mg/mLALOGPS
logP3.15ALOGPS
logP3.02ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)5.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area37.61 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.58 m3·mol-1ChemAxon
Polarizability35.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9392
Caco-2 permeable+0.6638
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IINon-inhibitor0.7574
Renal organic cation transporterNon-inhibitor0.621
CYP450 2C9 substrateNon-substrate0.7412
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateInhibitor0.624
CYP450 2C9 inhibitorNon-inhibitor0.8331
CYP450 2D6 inhibitorNon-inhibitor0.8754
CYP450 2C19 inhibitorNon-inhibitor0.9119
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5265
Ames testNon AMES toxic0.5507
CarcinogenicityNon-carcinogens0.8352
BiodegradationNot ready biodegradable0.9928
Rat acute toxicity2.5614 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9831
hERG inhibition (predictor II)Non-inhibitor0.6928
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-000i-1090000000-5429f5620534a2340098
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-0196000000-6304f5b37ed9f071eb26

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
Phenylimidazoles
Alternative Parents
Imidazopyridines / Imidazo[1,2-a]pyridines / Toluenes / Methylpyridines / N-substituted imidazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
5-phenylimidazole / 4-phenylimidazole / Imidazopyridine / Imidazo[1,2-a]pyridine / Toluene / Methylpyridine / Monocyclic benzene moiety / N-substituted imidazole / Pyridine / Benzenoid
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
imidazopyridine (CHEBI:10125)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Vlainic J, Pericic D: Effects of acute and repeated zolpidem treatment on pentylenetetrazole-induced seizure threshold and on locomotor activity: comparison with diazepam. Neuropharmacology. 2009 Jun;56(8):1124-30. doi: 10.1016/j.neuropharm.2009.03.010. Epub 2009 Apr 1. [PubMed:19345234]
  4. Smith AJ, Alder L, Silk J, Adkins C, Fletcher AE, Scales T, Kerby J, Marshall G, Wafford KA, McKernan RM, Atack JR: Effect of alpha subunit on allosteric modulation of ion channel function in stably expressed human recombinant gamma-aminobutyric acid(A) receptors determined using (36)Cl ion flux. Mol Pharmacol. 2001 May;59(5):1108-18. [PubMed:11306694]
  5. Pritchett DB, Seeburg PH: Gamma-aminobutyric acidA receptor alpha 5-subunit creates novel type II benzodiazepine receptor pharmacology. J Neurochem. 1990 May;54(5):1802-4. [PubMed:2157817]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
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
GABRA2
Uniprot ID
P47869
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight
51325.85 Da
References
  1. Pritchett DB, Seeburg PH: Gamma-aminobutyric acidA receptor alpha 5-subunit creates novel type II benzodiazepine receptor pharmacology. J Neurochem. 1990 May;54(5):1802-4. [PubMed:2157817]
  2. Smith AJ, Alder L, Silk J, Adkins C, Fletcher AE, Scales T, Kerby J, Marshall G, Wafford KA, McKernan RM, Atack JR: Effect of alpha subunit on allosteric modulation of ion channel function in stably expressed human recombinant gamma-aminobutyric acid(A) receptors determined using (36)Cl ion flux. Mol Pharmacol. 2001 May;59(5):1108-18. [PubMed:11306694]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
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
GABRA3
Uniprot ID
P34903
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight
55164.055 Da
References
  1. Pritchett DB, Seeburg PH: Gamma-aminobutyric acidA receptor alpha 5-subunit creates novel type II benzodiazepine receptor pharmacology. J Neurochem. 1990 May;54(5):1802-4. [PubMed:2157817]
  2. Smith AJ, Alder L, Silk J, Adkins C, Fletcher AE, Scales T, Kerby J, Marshall G, Wafford KA, McKernan RM, Atack JR: Effect of alpha subunit on allosteric modulation of ion channel function in stably expressed human recombinant gamma-aminobutyric acid(A) receptors determined using (36)Cl ion flux. Mol Pharmacol. 2001 May;59(5):1108-18. [PubMed:11306694]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Gaba-gated chloride ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRB3
Uniprot ID
P28472
Uniprot Name
Gamma-aminobutyric acid receptor subunit beta-3
Molecular Weight
54115.04 Da
References
  1. Hadingham KL, Garrett EM, Wafford KA, Bain C, Heavens RP, Sirinathsinghji DJ, Whiting PJ: Cloning of cDNAs encoding the human gamma-aminobutyric acid type A receptor alpha 6 subunit and characterization of the pharmacology of alpha 6-containing receptors. Mol Pharmacol. 1996 Feb;49(2):253-9. [PubMed:8632757]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRG2
Uniprot ID
P18507
Uniprot Name
Gamma-aminobutyric acid receptor subunit gamma-2
Molecular Weight
54161.78 Da
References
  1. Hadingham KL, Garrett EM, Wafford KA, Bain C, Heavens RP, Sirinathsinghji DJ, Whiting PJ: Cloning of cDNAs encoding the human gamma-aminobutyric acid type A receptor alpha 6 subunit and characterization of the pharmacology of alpha 6-containing receptors. Mol Pharmacol. 1996 Feb;49(2):253-9. [PubMed:8632757]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase 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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Data supporting this enzyme action is limited to in vitro studies.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423]
  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. Inagaki T, Miyaoka T, Tsuji S, Inami Y, Nishida A, Horiguchi J: Adverse reactions to zolpidem: case reports and a review of the literature. Prim Care Companion J Clin Psychiatry. 2010;12(6). doi: 10.4088/PCC.09r00849bro. [PubMed:21494350]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]
  2. Barkin RL: 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. doi: 10.1097/MJT.0b013e31804c7292. [PubMed:17515707]
  3. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 10:48