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

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, 17.

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.

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/1OralCaremark L.L.C.2007-04-172011-12-31Us
AmbienTablet, film coated10 mg/1Oralbryant ranch prepack1993-04-012009-10-01Us
AmbienTablet, film coated10 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2009-06-30Not applicableUs
AmbienTablet, film coated10 mg/1OralA S Medication Solutions1993-04-01Not applicableUs
AmbienTablet, film coated10 mg/1OralStat Rx USA1993-04-01Not applicableUs
AmbienTablet, film coated10 mg/1OralRebel Distributors2009-06-30Not applicableUs
AmbienTablet, film coated10 mg/1OralA-S Medication Solutions1993-04-012015-12-31Us
AmbienTablet, film coated5 mg/1OralA S Medication Solutions1993-04-01Not applicableUs
AmbienTablet, film coated10 mg/1OralPhysicians Total Care, Inc.1995-02-162012-06-30Us
AmbienTablet, film coated10 mg/1Oralsanofi-aventis U.S. LLC1993-04-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmbienTablet5 mg/1OralDirectrx2016-02-10Not applicableUs
AmbienTablet10 mg/1OralDirectrx2016-01-28Not applicableUs
Apo-zolpidem ODTTablet, orally disintegratingSublingualApotex Corporation2015-02-13Not applicableCanada
Apo-zolpidem ODTTablet, orally disintegratingSublingualApotex Corporation2015-02-13Not applicableCanada
Mint-zolpidem ODTTablet, orally disintegratingSublingualMint Pharmaceuticals IncNot applicableNot applicableCanada
Mint-zolpidem ODTTablet, orally disintegratingSublingualMint Pharmaceuticals IncNot applicableNot applicableCanada
PMS-zolpidem ODTTablet, orally disintegratingSublingualPharmascience Inc2016-12-13Not applicableCanada
PMS-zolpidem ODTTablet, orally disintegratingSublingualPharmascience Inc2016-12-13Not applicableCanada
ZolpidemTablet10 mg/1OralHikma Pharmaceuticals USA Inc.2008-04-30Not applicableUs
ZolpidemTablet5 mg/1OralHikma Pharmaceuticals USA Inc.2008-04-30Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Gabazolpidem-5Zolpidem tartrate (5 mg/1) + Choline (125 mg/1)KitOralPhysician 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

This drug is indicated for the short-term treatment of insomnia in adults characterized by difficulties with sleep initiation Label.

Associated Conditions
Pharmacodynamics

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 17, 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, 17.

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, 17. 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 17, 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.

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-1
agonist
Humans
UGamma-aminobutyric acid receptor subunit alpha-2
agonist
Humans
UGamma-aminobutyric acid receptor subunit alpha-3
agonist
Humans
UGamma-aminobutyric acid receptor subunit gamma-2
agonist
Humans
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

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.

Toxicity

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.

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

Interactions

Drug Interactions
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.
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.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Zolpidem can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
6-Deoxyerythronolide BThe metabolism of Zolpidem can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Zolpidem.
7-ethyl-10-hydroxycamptothecinThe metabolism of Zolpidem can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
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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]
  6. 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. [PubMed:15651908]
  7. 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. [PubMed:8521677]
  8. 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. [PubMed:24563183]
  9. 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. [PubMed:23462249]
  10. 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. [PubMed:26579377]
  11. 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. [PubMed:21353710]
  12. 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]
  13. 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. [PubMed:11090095]
  14. 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]
  15. NIH Stat Pearls, Internet: Zolpidem [Link]
  16. 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]
  17. 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
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 (259 KB)
MSDS
Download (170 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceDepression1
0Enrolling by InvitationOtherSleep1
0RecruitingTreatmentInsomnia Chronic1
0Unknown StatusBasic SciencePsychotropic Drugs Effects1
1CompletedNot AvailableAbuse Potential Study1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableTransient Insomnia1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Therapeutic Equivalency1
1CompletedBasic ScienceMarijuana Dependence1
1CompletedBasic ScienceMethodology Study1
1CompletedOtherHealthy Volunteers2
1CompletedTreatmentHealthy Recreational Drug Users1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentInsomnia3
1CompletedTreatmentInsomnia Disorders1
1CompletedTreatmentInsomnia / Sleep Initiation and Maintenance Disorders1
1RecruitingBasic ScienceProstatic Neoplasms1
1RecruitingTreatmentComplications, Arthroplasty / Perioperative/Postoperative Complications / Shoulder Arthritis / Sleep Disturbances1
1WithdrawnOtherHealthy Volunteers1
1, 2CompletedTreatmentInsomnia / Sleep Disorder1
2CompletedOtherInsomnia Disorder1
2CompletedTreatmentInsomnia Disorder1
2CompletedTreatmentInsomnia Disorders1
2CompletedTreatmentPrimary Insomnia / Secondary Insomnia1
2CompletedTreatmentSleep Initiation and Maintenance Disorders1
2CompletedTreatmentMinor burns / Sleep1
2RecruitingTreatmentParkinson's Disease (PD)1
2TerminatedTreatmentPrimary Insomnia1
2WithdrawnTreatmentParkinson's Disease (PD)1
2, 3Active Not RecruitingTreatmentPrimary Insomnia / Secondary Insomnia1
2, 3CompletedTreatmentPrimary Insomnia1
2, 3CompletedTreatmentSubstance, Addiction1
2, 3Not Yet RecruitingTreatmentInsomnia Disorder1
3CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
3CompletedTreatmentChild's Anxiety / Parental/Caregiver Anxiety1
3CompletedTreatmentInsomnia3
3CompletedTreatmentPrimary Insomnia1
3CompletedTreatmentSleep Initiation and Maintenance Disorders4
3CompletedTreatmentSleep disorders and disturbances / Sleep Initiation and Maintenance Disorders1
3RecruitingTreatmentAlzheimer's Disease (AD) / Insomnia / Sleep / Sleep disorders and disturbances1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentInsomnia1
4CompletedNot AvailablePostural Instability1
4CompletedBasic ScienceMemory / Sleep1
4CompletedDiagnosticHealthy Volunteers1
4CompletedOtherPsychomotor Impairment1
4CompletedSupportive CareCognition / Pharmacologic Actions / Sleep1
4CompletedTreatmentDepression / Insomnia / Suicidal Thoughts1
4CompletedTreatmentDepression / Sleep Initiation and Maintenance Disorders2
4CompletedTreatmentHeart Failure / Sleep Disturbances1
4CompletedTreatmentInsomnia6
4CompletedTreatmentInsomnia Chronic1
4CompletedTreatmentInsomnia / Primary Insomnia / Psychophysiologic Insomnia1
4CompletedTreatmentInsomnia / Sleep Initiation and Maintenance Disorders1
4CompletedTreatmentOSAS (Obstructive Sleep Apneas Syndrome)1
4CompletedTreatmentPrimary Insomnia / Sleep Initiation and Maintenance Disorders2
4CompletedTreatmentSleep Initiation and Maintenance Disorders1
4CompletedTreatmentSleep disorders and disturbances4
4Not Yet RecruitingTreatmentAble Bodied / Sleep Disordered Breathing (SDB)1
4RecruitingBasic ScienceAging1
4RecruitingTreatmentInsomnia Chronic1
4RecruitingTreatmentInsomnia / Insomnia Chronic1
4RecruitingTreatmentTreatments1
4TerminatedPreventionDelirium / Hip Fracture1
4Unknown StatusTreatmentAcute Coronary Syndromes (ACS) / Sleep Deprivation1
4Unknown StatusTreatmentDelirium1
4Unknown StatusTreatmentPrimary Insomnia1
4WithdrawnBasic ScienceHealthy Volunteers1
Not AvailableCompletedNot AvailableHealthy Volunteers4
Not AvailableCompletedNot AvailablePrimary Insomnia1
Not AvailableCompletedBasic ScienceInsomnia1
Not AvailableCompletedBasic SciencePhysiology1
Not AvailableCompletedHealth Services ResearchSleep1
Not AvailableCompletedSupportive CareBreast Cancer / 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 AvailableCompletedTreatmentInsomnia2
Not AvailableCompletedTreatmentInsomnia Comorbid to Psychiatric Disorder / Primary Insomnia1
Not AvailableCompletedTreatmentLiver Cirrhosis1
Not AvailableCompletedTreatmentPrimary Insomnia1
Not AvailableCompletedTreatmentSleep Initiation and Maintenance Disorders1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiety / Anxiolysis / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Bradycardia / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Cardiac Dysrhythmia / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Chronic Kidney Disease (CKD) / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infection / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Endocarditis / Epilepsies / Fibrinolytic Bleeding / Flu caused by Influenza / Gastroparesis / Gram-negative Infection / Gynaecological infection / Headache / Heart Failure / Heavy Menstrual Bleeding / Hemophilia / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperaldosteronism / Hyperlipidemias / Hypokalemia / Hypotension / Infantile Hemangiomas / Infection caused by staphylococci / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Insomnia / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Methicillin Resistant Staphylococcus Aureus (MRSA) / Migraine / Muscle Spasms / Nausea / Neuromuscular Blockade / Neutropenia / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Pulmonary Arterial Hypertension (PAH) / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infection / Vomiting / Withdrawal1
Not AvailableRecruitingNot AvailableSleep Disorder1
Not AvailableTerminatedSupportive CareNeoplasms, Endometrial / Pain / 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 disintegratingSublingual
TabletSublingual10 mg/1
TabletSublingual5 mg/1
KitOral
TabletSublingual1.75 mg/1
TabletSublingual3.5 mg/1
TabletOral
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
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)193-197MSDS
water solubility23 mg/mL at 20 CMSDS
logP3.02http://www.t3db.ca/toxins/T3D2787
pKaStrongest basic, 5.65http://foodb.ca/compounds/FDB023594
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
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
  1. 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]
  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]
  3. 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]
  4. Sramka M, Nadvornik P: Surgical complication of posterior hypothalamotomy. Confin Neurol. 1975;37(1-3):193-4. [PubMed:1093783]
  5. 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. [PubMed:21353710]
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
  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]
  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. 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. [PubMed:11090095]
  5. 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. [PubMed:21353710]
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
  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]
  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. 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. [PubMed:11090095]
  5. 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. [PubMed:21353710]
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
  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]
  2. 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]
  3. 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. [PubMed:7714808]

Enzymes

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
  1. 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. [PubMed:20552178]
  2. 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. [PubMed:25567214]
  3. 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
  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
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
  1. 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. [PubMed:30178440]
  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]
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
  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]
  4. 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. [PubMed:30178440]
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
  1. 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. [PubMed:30178440]
  2. 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. [PubMed:8591727]

Drug created on June 13, 2005 07:24 / Updated on December 08, 2019 13:52