TEMAZEPAM

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H13ClN2O2
Molecular Weight	300.74
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C2=CC=C(Cl)C=C2C(=NC(O)C1=O)C3=CC=CC=C3

InChI

InChIKey=SEQDDYPDSLOBDC-UHFFFAOYSA-N

InChI=1S/C16H13ClN2O2/c1-19-13-8-7-11(17)9-12(13)14(18-15(20)16(19)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3

HIDE SMILES / InChI

Molecular Formula	C16H13ClN2O2
Molecular Weight	300.74
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.drugbank.ca/drugs/DB00231
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018163s054lbl.pdf

Temazepam is a benzodiazepine used as a hypnotic agent in the management of insomnia. Temazepam produces CNS depression at limbic, thalamic, and hypothalamic levels of the CNS. Temazepam increases the affinity of the neurotransmitter gamma-aminobutyric acid (GABA) for GABA receptors by binding to benzodiazepine receptors. Results are sedation, hypnosis, skeletal muscle relaxation, anticonvulsant activity, and anxiolytic action. Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell. Temazepam is used for the short-term treatment of insomnia (generally 7-10 days).

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: http://www.genome.jp/dbget-bin/www_bget?D00370	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018163s054lbl.pdf	Primary		Approved 8583	Restoril Approved Use Restoril™ (temazepam) is indicated for the short-term treatment of insomnia (generally 7 to 10 days). Launch Date 1981

C_max

Value	Dose	Analyte	Population
1560 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2574013	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	TEMAZEPAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
964 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8181199	26 mg single, intravenous dose: 26 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
865 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/018163s065lbl.pdf	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TEMAZEPAM plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
6.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8181199	26 mg single, intravenous dose: 26 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TEMAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1800 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/018163s065lbl.pdf	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		TEMAZEPAM plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2574013	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	TEMAZEPAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8181199	26 mg single, intravenous dose: 26 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/018163s065lbl.pdf	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TEMAZEPAM plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8181199	26 mg single, intravenous dose: 26 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TEMAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/018163s065lbl.pdf	30 mg 1 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		TEMAZEPAM plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
26 mg single, intravenous Dose: 26 mg Route: intravenous Route: single Dose: 26 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8181199	healthy, 18 - 24 years Health Status: healthy Age Group: 18 - 24 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8181199	Sources: https://pubmed.ncbi.nlm.nih.gov/8181199
40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2574013	unhealthy, 42 years (range: 22 - 59 years) Health Status: unhealthy Age Group: 42 years (range: 22 - 59 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2574013	Sources: https://pubmed.ncbi.nlm.nih.gov/2574013

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A3 89 UGT2B7 197

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A3 99	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20111869/	yes
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20111869/	yes

Sourcing

Vendor/Aggregator	ID	URL
Alsachim	1614	http://www.alsachim.com/product-C3008-glo.bal-view.html
Ambinter	Amb13889605	http://www.ambinter.com/reference/13889605
Aurora Fine Chemicals LLC	A17.880.532	http://online.aurorafinechemicals.com/info?ID=A17.880.532
Aurora Fine Chemicals LLC	K02.121.169	http://online.aurorafinechemicals.com/info?ID=K02.121.169
Avantor Inc	75835-924	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
ChemMol	49413412	http://www.chemmol.com/chemmol/49413412.html
Clearsynth	CS-EB-02054	https://www.clearsynth.com/en/CSEB02054.html
Clearsynth	CS-ER-02054	https://www.clearsynth.com/en/CSER02054.html
iChemical	EBD3072653	http://www.ichemical.com/products/846-50-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
LGC Standards	LGCAMP0087.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP0087.00-01
LGC Standards	LGCFOR0087.00	https://www.lgcstandards.com/US/en/p/LGCFOR0087.00
LGC Standards	MM0087.00-0250	https://www.lgcstandards.com/US/en/p/MM0087.00-0250
Parchem	100802	https://www.parchem.com/chemical-supplier-distributor/Temazepam-100802.aspx
Sigma-Aldrich	1643408_USP	https://www.sigmaaldrich.com/catalog/product/usp/1643408?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP455_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp455?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T-907_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/t907?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T8275_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/t8275?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S544886	http://www.smolecule.com/products/s544886
THE BioTek	bt-284002	https://www.thebiotek.com/product/inhibitors/bt-284002

PubMed

Title	Date	PubMed
Effects of co-medicated drugs on cyclophosphamide bioactivation in human liver microsomes.	2005-03	15711186
[Diphenhydramin-overdose: anticholinergic symptoms, EEG-findings in the course and drug treatment of a gerontopsychiatric patient].	2004-11	15570534
Effects of zolpidem and temazepam on driving ability.	2004-11	15511711
Alcohol and other drug use in later life.	2004-10	15532157
The effects of restricting publicly subsidised temazepam capsules on benzodiazepine use among injecting drug users in Australia.	2004-09-20	15377238
'Hypnotic' prescription patterns in a large managed-care population.	2004-09	15341891
Strain differences in diazepam metabolism at its three metabolic sites in sprague-dawley, brown norway, dark agouti, and wistar strain rats.	2004-09	15319337
Screening, library-assisted identification and validated quantification of 23 benzodiazepines, flumazenil, zaleplone, zolpidem and zopiclone in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.	2004-08	15329838
Zolpidem is not superior to temazepam with respect to rebound insomnia: a controlled study.	2004-08	15163440
Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis.	2004-07	15252823
Sleep-inducing pharmaceuticals: a comparison of melatonin, zaleplon, zopiclone, and temazepam.	2004-06	15198277
Comparison of temazepam 7.5 mg with temazepam 15 mg for the treatment of transient insomnia.	2004-04	15119980
An assessment of quality of sleep and the use of drugs with sedating properties in hospitalized adult patients.	2004-03-24	15040803
[Benzodiazepines and forensic aspects].	2004-03-19	15029082
Evaluation of actigraphy and automated telephoned questionnaires to assess hypnotic effects in insomnia.	2004-03	15076015
Psychological treatment for insomnia in the regulation of long-term hypnotic drug use.	2004-02	14960254
A postmarketing study of relative abuse liability of hypnotic sedative drugs.	2004-02	14756709
Monitoring of drugs and metabolites in whole blood by restricted-access solid-phase microextraction coupled to liquid chromatography-mass spectrometry.	2004-01-30	14753675
CNS effects of sumatriptan and rizatriptan.	2004-01	14687019
Quantitation of drug metabolites in the absence of pure metabolite standards by high-performance liquid chromatography coupled with a chemiluminescence nitrogen detector and mass spectrometer.	2004	15282765
[Signopam treatment of insomnia in patients with somatic pathology].	2004	15272636
A near-fatal overdose of carisoprodol (SOMA): case report.	2004	15214630
Residual effects of hypnotics: epidemiology and clinical implications.	2004	15089115
Changes in fatalities due to overdose of anxiolytic and sedative drugs in the UK (1983-1999).	2004	14717623
Impact of melatonin, zaleplon, zopiclone, and temazepam on psychomotor performance.	2003-12	14692469
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.	2003-11-17	14612892
Chiral separations using polymeric surfactants and polyelectrolyte multilayers in open-tubular capillary electrochromatography.	2003-11-15	14615987
Effects of after-midnight intake of zolpidem and temazepam on driving ability in women with non-organic insomnia.	2003-11	14607350
Toward evidence-based prescribing at end of life: a comparative review of temazepam and zolpidem for the treatment of insomnia.	2003-10-08	14529041
The interactive effects of alcohol and temazepam on P300 and reaction time.	2003-10	14572503
Use of poly(sodium oleyl-L-leucylvalinate) surfactant for the separation of chiral compounds in micellar electrokinetic chromatography.	2003-09	12973797
Neurobehavioural performance effects of daytime melatonin and temazepam administration.	2003-09	12941059
[Comparative kinetics of 3-hydroxyphenazepam and its metabolism during transdermal and intravenous administration].	2003-08-20	12924236
Analytical developments in toxicological investigation of drug-facilitated sexual assault.	2003-08	12682705
Association of benzodiazepine injection with the prescription of temazepam capsules.	2003-06	12850901
Acute pharmacological effects of temazepam, diphenhydramine, and valerian in healthy elderly subjects.	2003-06	12826988
Case report: severe mercuric sulphate poisoning treated with 2,3-dimercaptopropane-1-sulphonate and haemodiafiltration.	2003-06	12793883
Fast analysis using monolithic columns coupled with high-flow on-line extraction and electrospray mass spectrometric detection for the direct and simultaneous quantitation of multiple components in plasma.	2003-05-25	12705973
Interaction of alcohol and drugs in fatal poisonings.	2003-05	12774892
Effects of diazepam and its metabolites on nocturnal melatonin secretion in the rat pineal and Harderian glands. A comparative in vivo and in vitro study.	2003-03	12723886
Errors in performance testing: a comparison of ethanol and temazepam.	2003-03	12680738
Improving daytime sleep with temazepam as a countermeasure for shift lag.	2003-02	12602447
Biomarkers for the effects of benzodiazepines in healthy volunteers.	2003-01	12534639
Adverse effects of temazepam in older adults with chronic insomnia.	2003-01	12532318
Pharmacokinetics and drug interactions of the sedative hypnotics.	2003	14561946
Simple and sensitive liquid chromatography/tandem mass spectrometry method for the determination of diazepam and its major metabolites in rat cerebrospinal fluid.	2003	12621612
Separation of oxazepam, lorazepam, and temazepam enantiomers by HPLC on a derivatized cyclodextrin-bonded phase: application to the determination of oxazepam in plasma.	2002-12-31	12543505
Recent trends in benzodiazepine use by injecting drug users in Victoria and Tasmania.	2002-12	12537706
Hypnotic medication in the aftermath of trauma.	2002-12	12530420
Anxiety in patients having caesarean section under regional anaesthesia: a questionnaire and pilot study.	2001-10	15321585

Patents

Sample Use Guides

In Vivo Use Guide

While the recommended usual adult dose is 15 mg before retiring, 7.5 mg may be sufficient for some patients, and others may need 30 mg. In transient insomnia, a 7.5 mg dose may be sufficient to improve sleep latency. In elderly or debilitated patients, it is recommended that therapy be initiated with 7.5 mg until individual responses are determined.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:28 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:28 GMT 2025`
Record UNII	CHB1QD2QSS
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TEMAZEPAM

Official Name

English

TEMAZEPAM CIV

Preferred Name

English

NSC-246303

Code

English

TEMAZEPAM [USAN]

Common Name

English

(RS)-TEMAZEPAM

Common Name

English

WY-3917

Code

English

TEMAZEPAM [ORANGE BOOK]

Common Name

English

(±)-TEMAZEPAM

Common Name

English

7-Chloro-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

Systematic Name

English

TEMAZEPAM [USP MONOGRAPH]

Common Name

English

Temazepam [WHO-DD]

Common Name

English

RESTORIL

Brand Name

English

TEMAZEPAM [MI]

Common Name

English

temazepam [INN]

Common Name

English

TEMAZEPAM [MART.]

Common Name

English

TEMAZEPAM [VANDF]

Common Name

English

TEMAZEPAM CIV [USP-RS]

Common Name

English

TEMAZEPAM [EP MONOGRAPH]

Common Name

English

2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-1,3-DIHYDRO-3-HYDROXY-1-METHYL-5-PHENYL-

Systematic Name

English

TEMAZEPAM [IARC]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05CD07