Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H21N3O |
Molecular Weight | 307.3895 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C3=CC=C(C)C=C3
InChI
InChIKey=ZAFYATHCZYHLPB-UHFFFAOYSA-N
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
Zolpidem is usually used for the treatment of insomnia as a hypnotic drug. It was also suggested to be effective in the treatment of dystonia in some studies. Zolpidem can be one of useful alternative pharmacological treatments for blepharospasm. Zolpidem interacts with a GABA-BZ receptor complex and shares some of the pharmacological properties of the benzodiazepines. In contrast to the benzodiazepines, which non-selectively bind to and activate all BZ receptor subtypes, zolpidem in vitro binds the BZ1 receptor preferentially with a high affinity ratio of the α1/α5 subunits. This selective binding of zolpidem on the BZ1 receptor is not absolute, but it may explain the relative absence of myorelaxant and anticonvulsant effects in animal studies as well as the preservation of deep sleep in human studies of zolpidem tartrate at hypnotic doses.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22922343 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AMBIEN Approved UseAmbien (zolpidem tartrate) is indicated for the short-term treatment of insomnia characterized by difficulties with sleep initiation. Ambien has been shown to decrease sleep latency for up to 35 days in controlled clinical studies [see Clinical Studies (14) Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
121 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
59 ng/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.5 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
26 h |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.5% |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
7.5% |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZOLPIDEM unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.5 mg/kg single, oral Highest studied dose Dose: 0.5 mg/kg Route: oral Route: single Dose: 0.5 mg/kg Sources: |
unhealthy, 2 - 12 years n = 65 Health Status: unhealthy Condition: sleep disturbances Age Group: 2 - 12 years Sex: M+F Population Size: 65 Sources: |
Other AEs: Psychiatric symptom, Gastrointestinal disorder (NOS)... Other AEs: Psychiatric symptom (6 patients) Sources: Gastrointestinal disorder (NOS) (6 patients) Nervous system disorder NOS (5 patients) |
300 mg single, oral Overdose |
unhealthy, 68 years n = 1 Health Status: unhealthy Condition: sleep disturbances Age Group: 68 years Sex: F Population Size: 1 Sources: |
Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 1 patient) Sources: |
50 mg 1 times / day steady, oral (max) Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 1959 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1959 Sources: |
Disc. AE: Drowsiness, Vertigo... AEs leading to discontinuation/dose reduction: Drowsiness (1.1%) Sources: Vertigo (0.8%) Amnesia (0.5%) Nausea (0.5%) Headache (0.4%) Fall (0.4%) |
90 mg 1 times / day steady, oral (max) Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult n = 1701 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1701 Sources: |
Disc. AE: Drowsiness, Dizziness... AEs leading to discontinuation/dose reduction: Drowsiness (0.5%) Sources: Dizziness (0.4%) Headache (0.5%) Nausea (0.6%) Vomiting (0.5%) |
600 mg single, oral Overdose |
unhealthy, adult n = 344 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 344 Sources: |
Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 10 patients) Sources: |
600 mg single, oral Overdose |
unhealthy, adult n = 54 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 54 Sources: |
Disc. AE: Somnolence, Coma... AEs leading to discontinuation/dose reduction: Somnolence (100%) Sources: Coma (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nervous system disorder NOS | 5 patients | 0.5 mg/kg single, oral Highest studied dose Dose: 0.5 mg/kg Route: oral Route: single Dose: 0.5 mg/kg Sources: |
unhealthy, 2 - 12 years n = 65 Health Status: unhealthy Condition: sleep disturbances Age Group: 2 - 12 years Sex: M+F Population Size: 65 Sources: |
Gastrointestinal disorder (NOS) | 6 patients | 0.5 mg/kg single, oral Highest studied dose Dose: 0.5 mg/kg Route: oral Route: single Dose: 0.5 mg/kg Sources: |
unhealthy, 2 - 12 years n = 65 Health Status: unhealthy Condition: sleep disturbances Age Group: 2 - 12 years Sex: M+F Population Size: 65 Sources: |
Psychiatric symptom | 6 patients | 0.5 mg/kg single, oral Highest studied dose Dose: 0.5 mg/kg Route: oral Route: single Dose: 0.5 mg/kg Sources: |
unhealthy, 2 - 12 years n = 65 Health Status: unhealthy Condition: sleep disturbances Age Group: 2 - 12 years Sex: M+F Population Size: 65 Sources: |
Death | grade 5, 1 patient Disc. AE |
300 mg single, oral Overdose |
unhealthy, 68 years n = 1 Health Status: unhealthy Condition: sleep disturbances Age Group: 68 years Sex: F Population Size: 1 Sources: |
Fall | 0.4% Disc. AE |
50 mg 1 times / day steady, oral (max) Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 1959 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1959 Sources: |
Headache | 0.4% Disc. AE |
50 mg 1 times / day steady, oral (max) Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 1959 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1959 Sources: |
Amnesia | 0.5% Disc. AE |
50 mg 1 times / day steady, oral (max) Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 1959 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1959 Sources: |
Nausea | 0.5% Disc. AE |
50 mg 1 times / day steady, oral (max) Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 1959 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1959 Sources: |
Vertigo | 0.8% Disc. AE |
50 mg 1 times / day steady, oral (max) Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 1959 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1959 Sources: |
Drowsiness | 1.1% Disc. AE |
50 mg 1 times / day steady, oral (max) Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult n = 1959 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1959 Sources: |
Dizziness | 0.4% Disc. AE |
90 mg 1 times / day steady, oral (max) Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult n = 1701 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1701 Sources: |
Drowsiness | 0.5% Disc. AE |
90 mg 1 times / day steady, oral (max) Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult n = 1701 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1701 Sources: |
Headache | 0.5% Disc. AE |
90 mg 1 times / day steady, oral (max) Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult n = 1701 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1701 Sources: |
Vomiting | 0.5% Disc. AE |
90 mg 1 times / day steady, oral (max) Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult n = 1701 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1701 Sources: |
Nausea | 0.6% Disc. AE |
90 mg 1 times / day steady, oral (max) Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: |
unhealthy, adult n = 1701 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 1701 Sources: |
Death | grade 5, 10 patients Disc. AE |
600 mg single, oral Overdose |
unhealthy, adult n = 344 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 344 Sources: |
Coma | 1 patient Disc. AE |
600 mg single, oral Overdose |
unhealthy, adult n = 54 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 54 Sources: |
Somnolence | 100% Disc. AE |
600 mg single, oral Overdose |
unhealthy, adult n = 54 Health Status: unhealthy Condition: sleep disturbances Age Group: adult Sex: unknown Population Size: 54 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
weak [IC50 99 uM] | ||||
weak | ||||
weak |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | yes (co-administration study) Comment: A single-dose interaction study with zolpidem tartrate 10 mg and rifampin (CYP3A4 inducer) 600 mg at steady-state levels in female subjects showed significant reductions of the AUC (-73%), Cmax (-58%), and T1/2 (-36 %) of zolpidem together |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Development and modulation of GABA(A) receptor-mediated neurotransmission in the CA1 region of prenatally protein malnourished rats. | 2001 |
|
[Zolpidem (ivadal) treatment of sleep disorders]. | 2001 |
|
Measurement of cerebral perfusion after zolpidem administration in the baboon model. | 2001 |
|
Future directions in the management of insomnia. | 2001 |
|
A psychiatric perspective on insomnia. | 2001 |
|
The acute effects of zolpidem compared to diazepam and lorazepam using radiotelemetry. | 2001 Apr |
|
Zolpidem, triazolam, and diazepam decrease distress vocalizations in mouse pups: differential antagonism by flumazenil and beta-Carboline-3-carboxylate-t-butyl ester (beta-CCt). | 2001 Apr |
|
Comparative effects of melatonin, zolpidem and diazepam on sleep, body temperature, blood pressure and heart rate measured by radiotelemetry in Wistar rats. | 2001 Aug |
|
Zolpidem use and hip fractures in older people. | 2001 Dec |
|
Delirium associated with zolpidem. | 2001 Dec |
|
[Zolpidem: the risk of tolerance and dependence according to case reports, systematic studies and recent molecularbiological data]. | 2001 Dec |
|
Diminished allopregnanolone enhancement of GABA(A) receptor currents in a rat model of chronic temporal lobe epilepsy. | 2001 Dec 1 |
|
Triazolam discrimination in squirrel monkeys distinguishes high-efficacy agonists from other benzodiazepines and non-benzodiazepine drugs. | 2001 Feb |
|
A structure-activity relationship study of the affinity of selected imidazo[1,2-a]pyridine derivatives, congeners of zolpidem, for the omega 1-subtype of the benzodiazepine receptor. | 2001 Jan-Feb |
|
Acute zolpidem overdose leading to coma and respiratory failure. | 2001 Jul |
|
[Homeopathic specialties as substitutes for benzodiazepines: double-blind vs. placebo study]. | 2001 Jul-Aug |
|
A double-blind, randomized and placebo-controlled study on the polysomnographic withdrawal effects of zopiclone, zolpidem and triazolam in healthy subjects. | 2001 Jun |
|
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. | 2001 May |
|
Characterization of discriminative stimulus effects of the neuroactive steroid pregnanolone. | 2001 May |
|
A double-blind comparative study of zolpidem versus zopiclone in the treatment of chronic primary insomnia. | 2001 May-Jun |
|
Toxicity of alpidem, a peripheral benzodiazepine receptor ligand, but not zolpidem, in rat hepatocytes: role of mitochondrial permeability transition and metabolic activation. | 2001 Nov |
|
Prevalence between different alpha subunits performing the benzodiazepine binding sites in native heterologous GABA(A) receptors containing the alpha2 subunit. | 2001 Oct |
|
Prediction of human hepatic clearance from in vivo animal experiments and in vitro metabolic studies with liver microsomes from animals and humans. | 2001 Oct |
|
Insomnia: therapeutic approach. | 2001 Sep |
|
Potency of positive gamma-aminobutyric acid(A) modulators to substitute for a midazolam discriminative stimulus in untreated monkeys does not predict potency to attenuate a flumazenil discriminative stimulus in diazepam-treated monkeys. | 2001 Sep |
|
Zolpidem in restless legs syndrome. | 2002 |
|
Melatonin for the prevention and treatment of jet lag. | 2002 |
|
The heterogeneity of central benzodiazepine receptor subtypes in the human hippocampal formation, frontal cortex and cerebellum using [3H]flumazenil and zolpidem. | 2002 Aug 15 |
|
Changes in GABA(A) receptor gene expression induced by withdrawal of, but not by long-term exposure to, zaleplon or zolpidem. | 2002 Feb |
|
[Epileptic seizures as a sign of abstinence from chronic consumption of zolpidem]. | 2002 Feb 1-15 |
|
Mechanism of alpha-subunit selectivity of benzodiazepine pharmacology at gamma-aminobutyric acid type A receptors. | 2002 Feb 15 |
|
Zolpidem improves dystonia in "Lubag" or X-linked dystonia-parkinsonism syndrome. | 2002 Feb 26 |
|
[Abuse, tolerance and dependence of zolpidem: three case reports]. | 2002 Jul-Aug |
|
Early cerebral activities of the environmental estrogen bisphenol A appear to act via the somatostatin receptor subtype sst(2). | 2002 Jun |
|
Zolpidem, vascular headache, and hallucinations in an adolescent. | 2002 Jun |
|
"As needed" pharmacotherapy combined with stimulus control treatment in chronic insomnia--assessment of a novel intervention strategy in a primary care setting. | 2002 Mar |
|
The effect of zolpidem on operant behavior and its relation to pharmacokinetics after intravenous and subcutaneous administration: concentration-effect relations. | 2002 Mar |
|
Soyka M, Bottlender R, Möller H-J; Epidemiological evidence for a low abuse potential of zolpidem; Pharmacopsychiatry 2000, 33: 138 - 141. | 2002 Mar |
|
Selective actions on sleep or anxiety by exploiting GABA-A/benzodiazepine receptor subtypes. | 2002 Mar |
|
Zolpidem in progressive supranuclear palsy. | 2002 Mar |
|
Sleep disorders and daytime sleepiness in state police shiftworkers. | 2002 Mar-Apr |
|
Clinical syndrome associated with zolpidem ingestion in dogs: 33 cases (January 1998-July 2000). | 2002 Mar-Apr |
|
Role of GABAA/benzodiazepine receptors containing alpha 1 and alpha 5 subunits in the discriminative stimulus effects of triazolam in squirrel monkeys. | 2002 May |
|
Selective modulation of tonic and phasic inhibitions in dentate gyrus granule cells. | 2002 May |
|
GABAA-benzodiazepine receptor complex ligands and stress-induced hyperthermia in singly housed mice. | 2002 May |
|
Rifampin and rifabutin drug interactions: an update. | 2002 May 13 |
|
Relation between discriminative and reinforcing effects of midazolam, pentobarbital, chlordiazepoxide, zolpidem, and imidazenil in baboons. | 2002 Oct |
|
Relative picrotoxin insensitivity distinguishes ionotropic GABA receptor-mediated IPSCs in hippocampal interneurons. | 2002 Sep |
|
GABA(A) receptor alpha-1 subunit deletion alters receptor subtype assembly, pharmacological and behavioral responses to benzodiazepines and zolpidem. | 2002 Sep |
|
Mechanisms of anabolic androgenic steroid modulation of alpha(1)beta(3)gamma(2L) GABA(A) receptors. | 2002 Sep |
Patents
Sample Use Guides
Dosage in Adults: the recommended initial dose is 5 mg for women and either 5 or 10 mg for men, taken only once per night immediately before bedtime with at least 7-8 hours remaining before the planned time of awakening. If the 5 mg dose is not effective, the dose can be increased to 10 mg. In some patients, the higher morning blood levels following use of the 10 mg dose increase the risk of next day impairment of driving and other activities that require full alertness. The total dose of AMBIEN (zolpidem tartrate) should not exceed 10 mg once daily immediately before bedtime. Ambien should be taken as a single dose and should not be readministered during the same night.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22922343
Human embryonic kidney (HEK) 293 cells stably expressing recombinant α1β2γ2s GABA(A) receptors were exposed to zolpidem (1 and 10 μmol/L) for short-term (2 h daily for 1, 2, or 3 consecutive days) or long-term (continuously for 48 h). Radioligand binding studies were used to determine the parameters of [(3)H]flunitrazepam binding sites. A single (2 h) or repeated (2 h daily for 2 or 3 d) short-term exposure to zolpidem affected neither the maximum number of [(3)H]flunitrazepam binding sites nor the affinity. In both control and short-term zolpidem treated groups, addition of GABA (1 nmol/L-1 mmol/L) enhanced [(3)H]flunitrazepam binding in a concentration-dependent manner. The maximum enhancement of [(3)H]flunitrazepam binding in short-term zolpidem treated group was not significantly different from that in the control group. In contrast, long-term exposure to zolpidem resulted in significantly increase in the maximum number of [(3)H]flunitrazepam binding sites without changing the affinity. Furthermore, long-term exposure to zolpidem significantly decreased the ability of GABA to stimulate [(3)H]flunitrazepam binding.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN05CF02
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NDF-RT |
N0000175759
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DEA NO. |
2783
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WHO-ATC |
N05CF02
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NCI_THESAURUS |
C29756
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LIVERTOX |
NBK547962
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5732
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ZOLPIDEM
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m11661
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N0000007570
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C62000
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ACTIVE MOIETY
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