Identification
- Summary
Zolpidem is a sedative hypnotic used for the short-term treatment of insomnia to improve sleep latency.
- Brand Names
- Ambien, Edluar, Intermezzo, Tovalt
- Generic Name
- Zolpidem
- DrugBank Accession Number
- DB00425
- Background
Zolpidem, also known as Ambien, is a hypnotic drug that was initially approved by the FDA in 1992 Label. Zolpidem improves sleep in patients with insomnia. It is aimed for use in patients with difficulties initiating sleep. This drug decreases the time to fall asleep (sleep latency), increases the duration of sleep, and decreases the number of awakenings during sleep in patients with temporary (transient) insomnia. It is available in both immediate acting and extended release forms Label, 18.
Its tolerability profile is favorable when administered according to the manufacturer’s instructions, with a low risk of drug withdrawal, drug dependence, and drug tolerance 6. In addition, zolpidem improves sleep quality in patients suffering from chronic insomnia and can show mild muscle relaxant properties 15. Research also shows that zolpidem is rapid and effective in restoring brain function for patients in a vegetative state following brain injury. This drug has the propensity to completely or partially reverse the abnormal metabolism of damaged brain cells after injury 15, 9.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Zolpidem (DB00425)
- Weight
- Average: 307.3895
Monoisotopic: 307.168462309 - Chemical Formula
- C19H21N3O
- 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
Pharmacology
- Indication
This drug is indicated for the short-term treatment of insomnia in adults characterized by difficulties with sleep initiation Label.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Insomnia •••••••••••• •••••• ••••••• ••••••• •••••••• ••••••• - Contraindications & Blackbox Warnings
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Effects on the central nervous system (CNS)
This drug has CNS depressant effects, which may include somnolence, decreased alertness, sedation, drowsiness, dizziness, and other changes in psychomotor function Label. Due to the above effects, the FDA has recommended an initial dose of zolpidem (immediate-acting) is a single dose of 5 mg for women and a single dose of 5 or 10 mg for men, immediately before bedtime with at least 7-8 hours remaining before the planned time of awakening 14. Refer to product labeling for detailed information 18, Label.
Effects on memory
Controlled studies in adults using objective measures of memory demonstrated no significant evidence of next-day memory impairment after the administration of zolpidem. On the contrary, in a clinical study involving the administration of zolpidem doses of 10 and 20 mg, a marked reduction in a next-morning recall of information relayed to subjects during peak drug effect (90 minutes after dosing) was observed. These subjects experienced a condition known as anterograde amnesia. Subjective evidence from adverse event data has suggested that anterograde amnesia may occur after zolpidem administration, mainly at doses above 10 mg Label.
Effects on psychomotor function
This drug may cause decreased psychomotor performance. Additive psychomotor effects may occur with other drugs that cause depression of psychomotor function, including alcohol Label. Patients taking zolpidem should be cautioned against participating in hazardous activities or occupations requiring complete mental alertness or motor coordination, including operating machinery or driving a motor vehicle after ingesting the drug. Potential impairment of the performance of the above types of activities may also occur the day after zolpidem ingestion, especially at higher doses and ingestion of the extended-release form Label, 18.
Effects on insomnia and sleep stages
Evidence suggests that this drug is associated with minimal rebound insomnia. During clinical trials with patients using zolpidem on an ‘as-needed’ basis, zolpidem use resulted in global improvements in sleep 6. Zolpidem has been demonstrated to decrease sleep latency (the time it takes to fall asleep) for up to 35 days in controlled clinical studies Label. In studies measuring the percentage of sleep time spent in each sleep stage, zolpidem has primarily been shown to preserve sleep stages. Sleep time spent in stages 3 and 4 (deep sleep) was measured as similar to placebo with only minor and inconsistent changes in REM (paradoxical) sleep at the recommended dose Label.
Next-day residual effects
In 2013, the FDA issued a statement warning that patients who take zolpidem extended-release (Ambien CR)―either 6.25 mg or 12.5 mg―should not drive or participate in other activities requiring full mental alertness the day after taking the drug, due to the fact that zolpidem concentrations can remain increased the next day, and impair the ability to perform these activities 14, 18. Patients may decrease their risk of next-morning impairment by taking the lowest dose of their insomnia medicine that treats their symptoms, according to the FDA 16. Specific dosing recommendations for both men and women are included in this statement 14. This information is also available on product labeling 18, Label.
Rebound effects
There was no polysomnographic (objective) evidence of rebound insomnia at normal doses, in studies evaluating sleep on the nights following discontinuation of zolpidem tartrate. Subjective evidence of impaired sleep in the elderly on the first post-treatment night was observed at doses higher than the recommended 5mg dose for elderly patients Label.
- Mechanism of action
Zolpidem, the active moiety of zolpidem tartrate, is a hypnotic substance with a chemical structure that is not related to the structure benzodiazepines, barbiturates, pyrrolopyrazines, pyrazolopyrimidines or other drugs exerting hypnotic effects. It interacts with a GABA-BZ receptor complex and shares various pharmacological properties with the benzodiazepine class of drugs Label.
Subunit binding of the GABAA receptor chloride channel macromolecular complex is thought to lead to the sedative, anticonvulsant, anxiolytic, and myorelaxant drug effects of zolpidem. The main regulatory site of the GABAA receptor complex can be found on its alpha (α) subunit and is called the benzodiazepine (BZ) or omega (ω) receptor. At least three different subtypes of the (ω) receptor have been identified to this date Label.
In contrast to benzodiazepine drugs, which are found to modulate all benzodiazepine receptor subtypes in a non-selective fashion, zolpidem binds the (BZ1) receptor specifically with a potent affinity for the alpha 1/alpha 5 subunits (in vitro) Label. More recent studies suggest that zolpidem binds primarily to the alpha 1, 2, and 3 subunits of the GABA receptor 11, 12, 13, and not the alpha 5 subunit.
The (BZ1) receptor is found primarily on the Lamina IV of the brain sensorimotor cortical regions, substantia nigra (pars reticulata), cerebellum molecular layer, olfactory bulb, ventral thalamic complex, pons, inferior colliculus, and globus pallidus. Specific and selective binding of zolpidem on the (BZ1) receptor is not considered absolute, however, this binding could potentially explain the relative lack of myorelaxant and anticonvulsant activity in animal studies in addition to the preservation of deep sleep (stages 3 and 4) in human studies of zolpidem at hypnotic doses Label.
Target Actions Organism AGamma-aminobutyric acid receptor subunit alpha-1 agonistHumans UGamma-aminobutyric acid receptor subunit alpha-2 agonistHumans UGamma-aminobutyric acid receptor subunit alpha-3 agonistHumans UGamma-aminobutyric acid receptor subunit gamma-2 agonistHumans - Absorption
Zolpidem is rapidly absorbed from the gastrointestinal tract. In a single-dose crossover study in 45 healthy subjects given 5 and 10 mg zolpidem tartrate tablets, the average peak zolpidem concentrations (Cmax) were 59 and 121 ng/mL, respectively, occurring at a mean time (Tmax) of 1.6 hours for both doses Label.
- Volume of distribution
0.54 to 0.68 L/kg (in humans) 7. In patients with long term renal insufficiency who were not yet on hemodialysis, the volume of distribution was found to increase significantly, AUC increased by 60%, and half-life nearly doubled 7.
- Protein binding
92.5 ± 0.1% Label
- Metabolism
Zolpidem is metabolized to three pharmacologically by various hepatic cytochrome P450 (CYP) isoenzymes, mainly CYP3A4, but also CYP1A2 and CYP2C9 7, 10. Although zolpidem is heavily metabolized, all three metabolites are inactive 6.
The major metabolic routes in humans are oxidation of the methyl group on the phenyl ring or the methyl group on the imidazopyridine moiety, to produce carboxylic acids (metabolites I and II), and hydroxylation of one of the imidazopyridine groups (to produce metabolite X). Another less common pathway is by the oxidation of the methyl groups on the substituted amide 7.
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- Route of elimination
Zolpidem tartrate tablets are converted to inactive metabolites that are eliminated mainly by renal excretion Label.
- Half-life
The average zolpidem elimination half-life was 2.6 and 2.5 hours, for the 5 and 10 mg tablets, respectively Label.
- Clearance
In a clinical trial, after a 20mg dose, total clearance of zolpidem 0.24 to 0.27 ml/min/kg 7.
- Adverse Effects
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Oral (male rat) LD50 = 695 mg/kg MSDS.
Overdose
Symptoms of overdose include impairment of consciousness ranging from somnolence to light coma, in addition to cardiorespiratory collapse resulting in fatal outcomes have been reported Label.
Withdrawal effects
Following rapid decreases in dose or abrupt discontinuation of zolpidem and other sedative/hypnotics, reports of signs and symptoms similar to those associated with withdrawal from other CNS-depressant drugs have been made Label.
Carcinogenesis
Zolpidem was administered to rats and mice over a span of 2 years at dietary dosages of 4, 18, and 80 mg/kg/day. In mice, these doses are considered 26 to 520 times or 2 to 35 times the maximum 10 mg human dose, respectively. In rats, these doses are 43 to 876 times or 6 to 115 times the maximum 10 mg human dose. No evidence of carcinogenicity was seen in mice. Renal liposarcomas were observed in 4/100 rats (3 males, 1 female) receiving 80 mg/kg/day, and a renal lipoma was observed in one male rat at the 18 mg/kg/day dose. Incidence rates of lipoma and liposarcoma for zolpidem were similar to those seen in historical control cases, and the tumor findings are presumed to be a spontaneous occurrence, not causally related to zolpidem Label.
Mutagenesis
Zolpidem did not show mutagenic activity in several tests including the Ames test, genotoxicity in mouse lymphoma cells in vitro, chromosomal aberrations in cultured human lymphocytes, abnormal DNA synthesis in rat hepatocytes in vitro, and the micronucleus test performed in mice Label.
Impairment of fertility
In a rat reproduction study, the high dose (100 mg base/kg) of zolpidem lead to irregular estrus cycles and prolonged precoital intervals, however, there was no effect on male or female fertility after daily oral doses comparable to 5 to 130 times the recommended human dose. No effects on any other fertility parameters were observed Label.
Use in pregnancy
This drug is considered a pregnancy category C drug. There are currently no sufficient conclusive studies completed in pregnant women to determine the safety of zolpidem use during pregnancy. Zolpidem should be used during pregnancy only if the potential benefit outweighs the potential risk to the fetus.
Use in nursing
From 0.004% to 0.019% of the total administered zolpidem dose is excreted into milk. The effect of zolpidem on the nursing infant is unknown at this time. Caution should be observed when zolpidem is administered to a nursing mother Label.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine 1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem. Abametapir The serum concentration of Zolpidem can be increased when it is combined with Abametapir. Abatacept The metabolism of Zolpidem can be increased when combined with Abatacept. Abiraterone The serum concentration of Zolpidem can be increased when it is combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Zolpidem. - Food Interactions
- Avoid alcohol.
- Take separate from meals. This drug should not be administered with or immediately after a meal.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Zolpidem tartrate WY6W63843K 99294-93-6 VXRDAMSNTXUHFX-CEAXSRTFSA-N - Product Images
- 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)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ambien Tablet, film coated 10 mg/1 Oral sanofi-aventis U.S. LLC 1993-04-01 Not applicable US 
Ambien Tablet, film coated 10 mg/1 Oral A-S Medication Solutions 1993-04-01 2015-12-31 US Ambien Tablet, film coated 5 mg/1 Oral Rebel Distributors 2009-06-30 Not applicable US Ambien Tablet, film coated 10 mg/1 Oral A S Medication Solutions 1993-04-01 Not applicable US Ambien Tablet, film coated 10 mg/1 Oral bryant ranch prepack 1993-04-01 2009-10-01 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-zolpidem ODT Tablet, orally disintegrating 10 mg Sublingual Angita Pharma Inc. Not applicable Not applicable Canada 
Ag-zolpidem ODT Tablet, orally disintegrating 5 mg Sublingual Angita Pharma Inc. Not applicable Not applicable Canada Ambien Tablet, film coated 5 mg/1 Oral Direct Rx 2016-02-10 Not applicable US Ambien Tablet, film coated 10 mg/1 Oral Direct Rx 2016-01-28 Not applicable US Apo-zolpidem ODT Tablet, orally disintegrating 5 mg Sublingual Apotex Corporation 2015-02-13 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image STILNOX CR 12.5mg Modified Release Tablet Zolpidem tartrate (6 mg) + Zolpidem tartrate (6.5 mg) Tablet, multilayer, extended release Oral SANOFI-AVENTIS SINGAPORE PTE. LTD. 2008-01-28 Not applicable Singapore 
STILNOX CR 12.5mg Modified Release Tablet Zolpidem tartrate (6 mg) + Zolpidem tartrate (6.5 mg) Tablet, multilayer, extended release Oral SANOFI-AVENTIS SINGAPORE PTE. LTD. 2008-01-28 Not applicable Singapore STILNOX CR 6.25mg Modified Release Tablet Zolpidem tartrate (3 mg) + Zolpidem tartrate (3.25 mg) Tablet, multilayer, extended release Oral SANOFI-AVENTIS SINGAPORE PTE. LTD. 2008-01-28 Not applicable Singapore STILNOX CR 6.25mg Modified Release Tablet Zolpidem tartrate (3 mg) + Zolpidem tartrate (3.25 mg) Tablet, multilayer, extended release Oral SANOFI-AVENTIS SINGAPORE PTE. LTD. 2008-01-28 Not applicable Singapore - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Gabazolpidem-5 Zolpidem tartrate (5 mg/1) + Choline (125 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US Sentrazolpidem PM-5 Zolpidem tartrate (5 mg/1) + Choline (250 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US
Categories
- ATC Codes
- N05CF02 — Zolpidem
- Drug Categories
- Benzodiazepine hypnotics and sedatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Central Nervous System Depression
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- GABA Agents
- GABA Agonists
- GABA-A Receptor Agonists
- gamma-Aminobutyric Acid-ergic Agonist
- Hypnotics (Nonbenzodiazepine)
- Hypnotics and Sedatives
- Miscellaneous Anxiolytics Sedatives and Hypnotics
- Nervous System
- Neurotransmitter Agents
- Psycholeptics
- Pyridines
- Sleep Aids, Pharmaceutical
- Chemical TaxonomyProvided by Classyfire
- 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
- 4-phenylimidazole / 5-phenylimidazole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative show 14 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- imidazopyridine (CHEBI:10125)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7K383OQI23
- CAS number
- 82626-48-0
- 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
References
- Synthesis Reference
Markus Sauter, "Process for preparing zolpidem." U.S. Patent US20020183522, issued December 05, 2002.
US20020183522- General References
- Lemmer B: The sleep-wake cycle and sleeping pills. Physiol Behav. 2007 Feb 28;90(2-3):285-93. Epub 2006 Oct 16. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Swainston Harrison T, Keating GM: Zolpidem: a review of its use in the management of insomnia. CNS Drugs. 2005;19(1):65-89. doi: 10.2165/00023210-200519010-00008. [Article]
- Salva P, Costa J: Clinical pharmacokinetics and pharmacodynamics of zolpidem. Therapeutic implications. Clin Pharmacokinet. 1995 Sep;29(3):142-53. doi: 10.2165/00003088-199529030-00002. [Article]
- Fitzgerald AC, Wright BT, Heldt SA: The behavioral pharmacology of zolpidem: evidence for the functional significance of alpha1-containing GABA(A) receptors. Psychopharmacology (Berl). 2014 May;231(9):1865-96. doi: 10.1007/s00213-014-3457-x. Epub 2014 Feb 22. [Article]
- Du B, Shan A, Zhang Y, Zhong X, Chen D, Cai K: Zolpidem arouses patients in vegetative state after brain injury: quantitative evaluation and indications. Am J Med Sci. 2014 Mar;347(3):178-82. doi: 10.1097/MAJ.0b013e318287c79c. [Article]
- Guo T, Mao G, Zhao L, Xia D, Yang L: Comparative pharmacokinetics of zolpidem tartrate in five ethnic populations of China. Acta Pharm Sin B. 2014 Apr;4(2):146-50. doi: 10.1016/j.apsb.2014.02.001. Epub 2014 Mar 15. [Article]
- Tan KR, Rudolph U, Luscher C: Hooked on benzodiazepines: GABAA receptor subtypes and addiction. Trends Neurosci. 2011 Apr;34(4):188-97. doi: 10.1016/j.tins.2011.01.004. Epub 2011 Feb 25. [Article]
- 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. [Article]
- Crestani F, Martin JR, Mohler H, Rudolph U: Mechanism of action of the hypnotic zolpidem in vivo. Br J Pharmacol. 2000 Dec;131(7):1251-4. doi: 10.1038/sj.bjp.0703717. [Article]
- FDA Drug Safety Communication: FDA approves new label changes and dosing for zolpidem products and a recommendation to avoid driving the day after using Ambien CR [Link]
- NIH Stat Pearls, Internet: Zolpidem [Link]
- Questions and Answers: Risk of next-morning impairment after use of insomnia drugs; FDA requires lower recommended doses for certain drugs containing zolpidem (Ambien, Ambien CR, Edluar, and Zolpimist) [Link]
- FDA Approved Drug Products: Ambien (zolpidem tartrate) oral tablets [Link]
- Ambien CR (extended release) label [File]
- External Links
- Human Metabolome Database
- HMDB0005023
- KEGG Compound
- C07219
- PubChem Compound
- 5732
- PubChem Substance
- 46507949
- ChemSpider
- 5530
- BindingDB
- 26266
- 39993
- ChEBI
- 10125
- ChEMBL
- CHEMBL911
- ZINC
- ZINC000000003876
- Therapeutic Targets Database
- DAP000112
- PharmGKB
- PA451976
- PDBe Ligand
- R5R
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Zolpidem
- PDB Entries
- 8dd2 / 8g4n / 8g5g / 8g5h
- FDA label
- Download (259 KB)
- MSDS
- Download (170 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Insomnia Chronic 1 4 Completed Not Available Postural Instability 1 4 Completed Basic Science Memory / Sleep 1 4 Completed Diagnostic Healthy Subjects (HS) 1 4 Completed Other Psychomotor Impairment 1
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
Form Route Strength Tablet Oral 10.000 mg Tablet, coated Oral 12.5 mg/1 Tablet, coated Oral 6.25 mg/1 Tablet, orally disintegrating Sublingual 10 mg Tablet, orally disintegrating Sublingual 5 mg Tablet Tablet Sublingual 10 mg/1 Tablet Sublingual 5 mg/1 Kit Oral Tablet Sublingual 1.75 mg/1 Tablet Sublingual 3.5 mg/1 Tablet Oral 10 mg Tablet Oral 5 mg Tablet Oral 5.000 mg Tablet Sublingual 5.00 mg Tablet Oral Solution / drops Oral Tablet Oral 10.00 mg Tablet, film coated Oral 10 MG Tablet, coated Oral 10 mg Tablet Oral 6.250 mg Tablet, multilayer, extended release Oral 6 mg Tablet, multilayer, extended release Oral 3 mg Tablet, coated Oral 5 mg Tablet, coated Oral 10.5 mg Tablet 10 MG Tablet 5 MG Tablet, film coated Oral 5 MG Capsule Oral 7.5 mg/1 Tablet Oral 10 mg/1 Tablet Oral 5 mg/1 Tablet, coated Oral 10 mg/1 Tablet, coated Oral 5 mg/1 Tablet, extended release Oral 12.5 mg/1 Tablet, extended release Oral 6.25 mg/1 Tablet, film coated Oral Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 5 mg/1 Tablet, film coated, extended release Oral 12.5 mg/1 Tablet, film coated, extended release Oral 6.25 mg/1 Spray, metered Oral 5 mg/1 - Prices
Unit description Cost Unit Ambien cr 12.5 mg tablet 6.19USD tablet Ambien cr 6.25 mg tablet 6.19USD tablet Ambien 10 mg tablet 6.11USD tablet Ambien 5 mg tablet 6.04USD tablet Ambien CR 12.5 mg Controlled Release Tabs 6.0USD tab Ambien CR 6.25 mg Controlled Release Tabs 6.0USD tab Edluar 10 mg sl tablet 5.0USD tablet Edluar 5 mg sl tablet 5.0USD tablet Zolpidem tartrate 10 mg tablet 2.73USD tablet Zolpidem tartrate 5 mg tablet 2.73USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6761910 No 2004-07-13 2019-09-24 US US8512747 No 2013-08-20 2019-09-24 US US9265720 No 2016-02-23 2030-05-13 US US6514531 Yes 2003-02-04 2020-06-01 US US7632517 No 2009-12-15 2017-10-01 US US7658945 No 2010-02-09 2027-04-15 US US7682628 No 2010-03-23 2025-02-16 US US8242131 No 2012-08-14 2029-08-20 US US8252809 No 2012-08-28 2025-02-16 US US9597281 No 2017-03-21 2027-04-06 US US8236285 No 2012-08-07 2032-08-07 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 193-197 MSDS water solubility 23 mg/mL at 20 C MSDS logP 3.02 http://www.t3db.ca/toxins/T3D2787 pKa Strongest basic, 5.65 http://foodb.ca/compounds/FDB023594 - Predicted Properties
Property Value Source Water Solubility 0.0313 mg/mL ALOGPS logP 3.15 ALOGPS logP 3.02 Chemaxon logS -4 ALOGPS pKa (Strongest Basic) 5.39 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 37.61 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 93.58 m3·mol-1 Chemaxon Polarizability 35.06 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9392 Caco-2 permeable + 0.6638 P-glycoprotein substrate Substrate 0.5 P-glycoprotein inhibitor I Inhibitor 0.8564 P-glycoprotein inhibitor II Non-inhibitor 0.7574 Renal organic cation transporter Non-inhibitor 0.621 CYP450 2C9 substrate Non-substrate 0.7412 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Inhibitor 0.624 CYP450 2C9 inhibitor Non-inhibitor 0.8331 CYP450 2D6 inhibitor Non-inhibitor 0.8754 CYP450 2C19 inhibitor Non-inhibitor 0.9119 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5265 Ames test Non AMES toxic 0.5507 Carcinogenicity Non-carcinogens 0.8352 Biodegradation Not ready biodegradable 0.9928 Rat acute toxicity 2.5614 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9831 hERG inhibition (predictor II) Non-inhibitor 0.6928
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 192.2494667 predictedDarkChem Lite v0.1.0 [M-H]- 191.5657667 predictedDarkChem Lite v0.1.0 [M-H]- 175.38863 predictedDeepCCS 1.0 (2019) [M+H]+ 193.3277667 predictedDarkChem Lite v0.1.0 [M+H]+ 192.6384667 predictedDarkChem Lite v0.1.0 [M+H]+ 177.74663 predictedDeepCCS 1.0 (2019) [M+Na]+ 192.7515667 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.84337 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- 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
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Sramka M, Nadvornik P: Surgical complication of posterior hypothalamotomy. Confin Neurol. 1975;37(1-3):193-4. [Article]
- Tan KR, Rudolph U, Luscher C: Hooked on benzodiazepines: GABAA receptor subtypes and addiction. Trends Neurosci. 2011 Apr;34(4):188-97. doi: 10.1016/j.tins.2011.01.004. Epub 2011 Feb 25. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Crestani F, Martin JR, Mohler H, Rudolph U: Mechanism of action of the hypnotic zolpidem in vivo. Br J Pharmacol. 2000 Dec;131(7):1251-4. doi: 10.1038/sj.bjp.0703717. [Article]
- Tan KR, Rudolph U, Luscher C: Hooked on benzodiazepines: GABAA receptor subtypes and addiction. Trends Neurosci. 2011 Apr;34(4):188-97. doi: 10.1016/j.tins.2011.01.004. Epub 2011 Feb 25. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Crestani F, Martin JR, Mohler H, Rudolph U: Mechanism of action of the hypnotic zolpidem in vivo. Br J Pharmacol. 2000 Dec;131(7):1251-4. doi: 10.1038/sj.bjp.0703717. [Article]
- Tan KR, Rudolph U, Luscher C: Hooked on benzodiazepines: GABAA receptor subtypes and addiction. Trends Neurosci. 2011 Apr;34(4):188-97. doi: 10.1016/j.tins.2011.01.004. Epub 2011 Feb 25. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- Criswell HE, Simson PE, Knapp DJ, Devaud LL, McCown TJ, Duncan GE, Morrow AL, Breese GR: Effect of zolpidem on gamma-aminobutyric acid (GABA)-induced inhibition predicts the interaction of ethanol with GABA on individual neurons in several rat brain regions. J Pharmacol Exp Ther. 1995 Apr;273(1):526-36. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- Byeon JY, Kim YH, Kim SH, Lee CM, Jung EH, Chae WK, Jang CG, Lee SY, Lee YJ: The influences of CYP2C9*1/*3 genotype on the pharmacokinetics of zolpidem. Arch Pharm Res. 2018 Sep;41(9):931-936. doi: 10.1007/s12272-018-1070-y. Epub 2018 Sep 3. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Byeon JY, Kim YH, Kim SH, Lee CM, Jung EH, Chae WK, Jang CG, Lee SY, Lee YJ: The influences of CYP2C9*1/*3 genotype on the pharmacokinetics of zolpidem. Arch Pharm Res. 2018 Sep;41(9):931-936. doi: 10.1007/s12272-018-1070-y. Epub 2018 Sep 3. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Byeon JY, Kim YH, Kim SH, Lee CM, Jung EH, Chae WK, Jang CG, Lee SY, Lee YJ: The influences of CYP2C9*1/*3 genotype on the pharmacokinetics of zolpidem. Arch Pharm Res. 2018 Sep;41(9):931-936. doi: 10.1007/s12272-018-1070-y. Epub 2018 Sep 3. [Article]
- Pichard L, Gillet G, Bonfils C, Domergue J, Thenot JP, Maurel P: Oxidative metabolism of zolpidem by human liver cytochrome P450S. Drug Metab Dispos. 1995 Nov;23(11):1253-62. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Cubala WJ, Wiglusz M, Burkiewicz A, Galuszko-Wegielnik M: Zolpidem pharmacokinetics and pharmacodynamics in metabolic interactions involving CYP3A: sex as a differentiating factor. Eur J Clin Pharmacol. 2010 Sep;66(9):955; author reply 957-8. doi: 10.1007/s00228-010-0854-x. Epub 2010 Jun 16. [Article]
- Galitz LA, Jayawardena S, Furey SA: Pharmacokinetic effects of simultaneous administration of single-dose gabapentin 500 mg and zolpidem tartrate 10 mg in healthy volunteers: a randomized, open-label, crossover trial. Drugs R D. 2015 Mar;15(1):71-7. doi: 10.1007/s40268-014-0079-z. [Article]
- Ambien FDA label [File]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55