Zolpidem tartrate

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C19H21N3O.C4H6O6
Molecular Weight	764.8659
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C3=CC=C(C)C=C3.CN(C)C(=O)CC4=C(N=C5C=CC(C)=CN45)C6=CC=C(C)C=C6

InChI

InChIKey=VXRDAMSNTXUHFX-CEAXSRTFSA-N

InChI=1S/2C19H21N3O.C4H6O6/c2*1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19;5-1(3(7)8)2(6)4(9)10/h2*5-10,12H,11H2,1-4H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1

HIDE SMILES / InChI

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C19H21N3O
Molecular Weight	307.3895
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019908s038lbl.pdf

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
GABA-A receptor; alpha-1/beta-2/gamma-2 28 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22922343	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019908s038lbl.pdf	Primary		Approved 8583	AMBIEN Approved Use Ambien (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 Date 1992

C_max

Value	Dose	Co-administered	Analyte	Population
59 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019908s027lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		ZOLPIDEM plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
121 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019908s027lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		ZOLPIDEM plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
26 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019908s027lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		ZOLPIDEM plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019908s027lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		ZOLPIDEM plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
7.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019908s027lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		ZOLPIDEM plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
7.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/019908s027lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		ZOLPIDEM plasma	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: https://pubmed.ncbi.nlm.nih.gov/17957186/	unhealthy, 2 - 12 years Health Status: unhealthy Age Group: 2 - 12 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17957186/	Other AEs: Psychiatric symptom, Gastrointestinal disorder (NOS)... Other AEs: Psychiatric symptom (6 patients) Gastrointestinal disorder (NOS) (6 patients) Nervous system disorder NOS (5 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17957186/
300 mg single, oral Overdose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8635759/	unhealthy, 68 years Health Status: unhealthy Age Group: 68 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/8635759/	Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8635759/
50 mg 1 times / day steady, oral Highest studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019908s035,021774s016lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019908s035,021774s016lbl.pdf	Disc. AE: Drowsiness, Vertigo... AEs leading to discontinuation/dose reduction: Drowsiness (1.1%) Vertigo (0.8%) Amnesia (0.5%) Nausea (0.5%) Headache (0.4%) Fall (0.4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019908s035,021774s016lbl.pdf
90 mg 1 times / day steady, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: steady Dose: 90 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019908s035,021774s016lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019908s035,021774s016lbl.pdf	Disc. AE: Drowsiness, Dizziness... AEs leading to discontinuation/dose reduction: Drowsiness (0.5%) Dizziness (0.4%) Headache (0.5%) Nausea (0.6%) Vomiting (0.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019908s035,021774s016lbl.pdf
600 mg single, oral Overdose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10517569/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/10517569/	Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 10 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10517569/
600 mg single, oral Overdose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8693299/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/8693299/	Disc. AE: Somnolence, Coma... AEs leading to discontinuation/dose reduction: Somnolence (100%) Coma (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8693299/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C19 2057 CYP3A 227 P-gp 1741	CYP1A2 1197 CYP2C19 1119

Drug as perpetrator

Target	Modality	Activity
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12469329/	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12469329/	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12469329/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12469329/	no
CYP3A 317	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12469329/	weak [IC50 99 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12469329/	weak
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12469329/	weak

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10383565/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10383565/	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10383565/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10383565/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10383565/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019908s037lbl.pdf	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 Sources: https://pubmed.ncbi.nlm.nih.gov/10383565/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019908s037lbl.pdf

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/23061993/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:10125	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:10125
ChemicalBook	CB14188703	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB14188703
ChemicalBook	CB44188704	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB44188704
ChemicalBook	CB83360349	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB83360349
ChemicalBook	CB84188702	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB84188702
eMolecules	596284	https://www.emolecules.com/cgi-bin/more?vid=596284
ZINC	ZINC000000003876	http://zinc15.docking.org/substances/ZINC000000003876

PubMed

Title	Date	PubMed
Relation between discriminative and reinforcing effects of midazolam, pentobarbital, chlordiazepoxide, zolpidem, and imidazenil in baboons.	2002-10	12373448
Functional characterization of GABA(A) receptors in neonatal hypothalamic brain slice.	2002-10	12364495
Zolpidem pharmacokinetic properties in young females: influence of smoking and oral contraceptive use.	2002-10	12362929
Comparison of the effects of zaleplon, zolpidem, and triazolam at various GABA(A) receptor subtypes.	2002-09-13	12231378
[Abuse, tolerance and dependence of zolpidem: three case reports].	2002-09-10	12217277
Relative picrotoxin insensitivity distinguishes ionotropic GABA receptor-mediated IPSCs in hippocampal interneurons.	2002-09	12367618
GABA(A) receptor alpha-1 subunit deletion alters receptor subtype assembly, pharmacological and behavioral responses to benzodiazepines and zolpidem.	2002-09	12367614
Mechanisms of anabolic androgenic steroid modulation of alpha(1)beta(3)gamma(2L) GABA(A) receptors.	2002-09	12367607
Sleep disorders and daytime sleepiness in state police shiftworkers.	2002-08-27	12194162
The heterogeneity of central benzodiazepine receptor subtypes in the human hippocampal formation, frontal cortex and cerebellum using [3H]flumazenil and zolpidem.	2002-08-15	12225875
Severe impairment of NMDA receptor function in mice carrying targeted point mutations in the glycine binding site results in drug-resistant nonhabituating hyperactivity.	2002-08-01	12151550
Hallucinations and Zolpidem.	2002-08	12199269
Imaging the GABA-benzodiazepine receptor subtype containing the alpha5-subunit in vivo with [11C]Ro15 4513 positron emission tomography.	2002-07	12142573
Early cerebral activities of the environmental estrogen bisphenol A appear to act via the somatostatin receptor subtype sst(2).	2002-06	12060835
Zolpidem, vascular headache, and hallucinations in an adolescent.	2002-06	12060196
Adaptive time-frequency parametrization in pharmaco EEG.	2002-05-30	12084565
[Epileptic seizures as a sign of abstinence from chronic consumption of zolpidem].	2002-05-22	12022074
Rifampin and rifabutin drug interactions: an update.	2002-05-13	11996607
Long term benzodiazepine use for insomnia in patients over the age of 60: discordance of patient and physician perceptions.	2002-05-08	12019038
Anxiolytic-like effects of acute and chronic GABA transporter inhibition in rats.	2002-05	12111474
Role of GABAA/benzodiazepine receptors containing alpha 1 and alpha 5 subunits in the discriminative stimulus effects of triazolam in squirrel monkeys.	2002-05	11981598
Selective modulation of tonic and phasic inhibitions in dentate gyrus granule cells.	2002-05	11976398
GABAA-benzodiazepine receptor complex ligands and stress-induced hyperthermia in singly housed mice.	2002-05	11900786
[Unexplained increase in aminotransferases and obstructive sleep apnea syndrome].	2002-04	12070418
Clinical syndrome associated with zolpidem ingestion in dogs: 33 cases (January 1998-July 2000).	2002-03-20	11899040
"As needed" pharmacotherapy combined with stimulus control treatment in chronic insomnia--assessment of a novel intervention strategy in a primary care setting.	2002-03	12046635
The effect of zolpidem on operant behavior and its relation to pharmacokinetics after intravenous and subcutaneous administration: concentration-effect relations.	2002-03	11981222
Soyka M, Bottlender R, Möller H-J; Epidemiological evidence for a low abuse potential of zolpidem; Pharmacopsychiatry 2000, 33: 138 - 141.	2002-03	11951152
Selective actions on sleep or anxiety by exploiting GABA-A/benzodiazepine receptor subtypes.	2002-03	11926714
Zolpidem in progressive supranuclear palsy.	2002-03	11882066
Zolpidem improves dystonia in "Lubag" or X-linked dystonia-parkinsonism syndrome.	2002-02-26	11865155
Mechanism of alpha-subunit selectivity of benzodiazepine pharmacology at gamma-aminobutyric acid type A receptors.	2002-02-15	11864636
[Pharmacological profile and clinical effect of zolpidem (Myslee tablets), a hypnotic agent].	2002-02	11862759
Discriminative stimulus effects of benzodiazepine (BZ)(1) receptor-selective ligands in rhesus monkeys.	2002-02	11805210
Changes in GABA(A) receptor gene expression induced by withdrawal of, but not by long-term exposure to, zaleplon or zolpidem.	2002-02	11804615
Fibromyalgia: patient perspectives on symptoms, symptom management, and provider utilization.	2002-01	11839925
Continuous versus non-nightly use of zolpidem in chronic insomnia: results of a large-scale, double-blind, randomized, outpatient study.	2002-01	11800507
Comparative meta-analysis of pharmacotherapy and behavior therapy for persistent insomnia.	2002-01	11772681
Zolpidem in restless legs syndrome.	2002	12373037
Tolerability of hypnosedatives in older patients.	2002	12182689
Melatonin for the prevention and treatment of jet lag.	2002	12076414
Diminished allopregnanolone enhancement of GABA(A) receptor currents in a rat model of chronic temporal lobe epilepsy.	2001-12-01	11731578
Zolpidem use and hip fractures in older people.	2001-12	11844004
Assessing the effects of an intervention by a pharmacist on prescribing and administration of hypnotics in nursing homes.	2001-12	11826512
Delirium associated with zolpidem.	2001-12	11793620
[Zolpidem: the risk of tolerance and dependence according to case reports, systematic studies and recent molecularbiological data].	2001-12	11753748
Arousal from a semi-comatose state on zolpidem.	2001-10	11732448
WHO Expert Committee on Drug Dependence. Thirty-second report.	2001	11851193
Development and modulation of GABA(A) receptor-mediated neurotransmission in the CA1 region of prenatally protein malnourished rats.	2001	11842879
[Correction of sleep disorders and efficacy of antihypertensive monotherapy in elderly patients: use of ivadal].	2001	11763525

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:27 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:27 GMT 2025`
Record UNII	WY6W63843K
Record Status	`Validated (UNII)`
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Name

Type

Language

Zolpidem tartrate

Official Name

English

Imidazo[1,2-a]pyridine-3-acetamide, N,N,6-trimethyl-2-(4-methylphenyl)-, [R-(R*,R*)]-2,3-dihydroxybutanedioate (2:1)

Preferred Name

English

(2R,3R)-2,3-DIHYDROXYSUCCINIC ACID - N,N-DIMETHYL-2-(6-METHYL-2-(4-METHYLPHENYL)IMIDAZO(1,2-A)PYRIDIN-3-YL)ACETAMIDE (1:2)

Common Name

English

AMBIEN

Brand Name

English

STILNOX

Brand Name

English

Zolpidem tartrate [MART.]

Common Name

English

SL-80.0750

Code

English

N,N,6-TRIMETHYL-2-P-TOLYL-IMIDAZO(1,2-A)PYRIDINE-3-ACETAMIDE L-(+)-HEMITARTRATE (2:1)

Common Name

English

Zolpidem tartrate [WHO-DD]

Common Name

English

Zolpidem tartrate CIV

Common Name

English

Zolpidem hemitartrate

Common Name

English

N,N,6-TRIMETHYL-2-P-TOLYLIMIDAZO(1,2-A)PYRIDINE-3-ACETAMIDE L-(+)-TARTRATE (2:1)

Common Name

English

ZOLPIDEM L-(+)-HEMITARTRATE [MI]

Common Name

English

MYSLEE

Brand Name

English

Zolpidem tartrate [ORANGE BOOK]

Common Name

English

Intermezzo

Brand Name

English

Ivadal

Brand Name

English

Zolpidem tartrate [EP MONOGRAPH]

Common Name

English

NIOTAL

Brand Name

English

Zolpidem tartrate [USP MONOGRAPH]

Common Name

English

Zolpidem tartrate[JAN]

Common Name

English

Zolpidem tartrate [USAN]

Common Name

English

SL-80.0750-23N

Code

English

SL 80.0750-23N

Code

English

Zolpidem tartrate [HSDB]

Common Name

English

STILNOCT

Brand Name

English

Zolpidem tartrate CIV [USP-RS]

Common Name

English

TOVALT

Brand Name

English

ZOLPIDEM L-(+)-HEMITARTRATE

Common Name

English

Zolpidem tartrate [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29756