TEMAZEPAM

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H13ClN2O2
Molecular Weight	300.7402
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1c2ccc(cc2C(=NC(C1=O)O)c3ccccc3)Cl

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

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 189 Target ID: CHEMBL2093872 Sources: http://www.genome.jp/dbget-bin/www_bget?D00370	Agonist 2470

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 100 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018163s054lbl.pdf	Primary		Approved 8043	Restoril Approved Use Restoril™ (temazepam) is indicated for the short-term treatment of insomnia (generally 7 to 10 days). Launch Date 3.51993594E11

C_max

Value	Dose	Analyte	Population
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
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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
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

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) n = 14 Health Status: unhealthy Age Group: 42 years (range: 22 - 59 years) Sex: M+F Population Size: 14 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 82 UGT2B7 141

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A3 91	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/20111869/	yes
UGT2B7 152	inhibitor 3045 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
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	T-907_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/t907?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	T8275_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/t8275?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1643408_USP	https://www.sigmaaldrich.com/catalog/product/usp/1643408?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
iChemical	EBD3072653	http://www.ichemical.com/products/846-50-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Anxiety in patients having caesarean section under regional anaesthesia: a questionnaire and pilot study.	2001 Oct	15321585
High-speed gradient parallel liquid chromatography/tandem mass spectrometry with fully automated sample preparation for bioanalysis: 30 seconds per sample from plasma.	2002	11992516
Use of night-time benzodiazepines in an elderly inpatient population.	2002 Apr	11975692
Digit loss following misuse of temazepam.	2002 Apr 15	12041634
Recent trends in benzodiazepine use by injecting drug users in Victoria and Tasmania.	2002 Dec	12537706
Microsomal protein concentration modifies the apparent inhibitory potency of CYP3A inhibitors.	2002 Dec	12433817
Separation of oxazepam, lorazepam, and temazepam enantiomers by HPLC on a derivatized cyclodextrin-bonded phase: application to the determination of oxazepam in plasma.	2002 Dec 31	12543505
Mechanism of increased dissolution of diazepam and temazepam from polyethylene glycol 6000 solid dispersions.	2002 Dec 5	12433433
Alcohol and benzodiazepines in fatal poisonings.	2002 Jul	12170103
Acute performance-impairing and subject-rated effects of triazolam and temazepam, alone and in combination with ethanol, in humans.	2002 Mar	11949768
Prediction of poly(ethylene) glycol-drug eutectic compositions using an index based on the van't Hoff equation.	2002 Mar	11934239
CNS effects of sumatriptan and rizatriptan in healthy female volunteers.	2002 May	12100089
Long term benzodiazepine use for insomnia in patients over the age of 60: discordance of patient and physician perceptions.	2002 May 8	12019038
Determination of the enantiomerization energy barrier of some 3-hydroxy-1,4-benzodiazepine drugs by supercritical fluid chromatography.	2002 Nov 5	12361742
Simple and sensitive liquid chromatography/tandem mass spectrometry method for the determination of diazepam and its major metabolites in rat cerebrospinal fluid.	2003	12621612
Analytical developments in toxicological investigation of drug-facilitated sexual assault.	2003 Aug	12682705
Impact of melatonin, zaleplon, zopiclone, and temazepam on psychomotor performance.	2003 Dec	14692469
Biomarkers for the effects of benzodiazepines in healthy volunteers.	2003 Jan	12534639
Adverse effects of temazepam in older adults with chronic insomnia.	2003 Jan	12532318
Analysis of homotropic and heterotropic cooperativity of diazepam oxidation by CYP3A4 using site-directed mutagenesis and kinetic modeling.	2003 Jan 1	12464248
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 Mar	12723886
[Comparative kinetics of 3-hydroxyphenazepam and its metabolism during transdermal and intravenous administration].	2003 May-Jun	12924236
Effects of after-midnight intake of zolpidem and temazepam on driving ability in women with non-organic insomnia.	2003 Nov	14607350
Chiral separations using polymeric surfactants and polyelectrolyte multilayers in open-tubular capillary electrochromatography.	2003 Nov 15	14615987
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.	2003 Nov 17	14612892
[Benzodiazepines and forensic aspects].	2003 Nov-Dec	15029082
The interactive effects of alcohol and temazepam on P300 and reaction time.	2003 Oct	14572503
Pharmacokinetics and drug interactions of the sedative hypnotics.	2003 Winter	14561946
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
Comparison of temazepam 7.5 mg with temazepam 15 mg for the treatment of transient insomnia.	2004 Apr	15119980
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 Aug	15329838
Zolpidem is not superior to temazepam with respect to rebound insomnia: a controlled study.	2004 Aug	15163440
Psychological treatment for insomnia in the regulation of long-term hypnotic drug use.	2004 Feb	14960254
A postmarketing study of relative abuse liability of hypnotic sedative drugs.	2004 Feb	14756709
CNS effects of sumatriptan and rizatriptan.	2004 Jan	14687019
Monitoring of drugs and metabolites in whole blood by restricted-access solid-phase microextraction coupled to liquid chromatography-mass spectrometry.	2004 Jan 30	14753675
Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis.	2004 Jul	15252823
Sleep-inducing pharmaceuticals: a comparison of melatonin, zaleplon, zopiclone, and temazepam.	2004 Jun	15198277
Evaluation of actigraphy and automated telephoned questionnaires to assess hypnotic effects in insomnia.	2004 Mar	15076015
An assessment of quality of sleep and the use of drugs with sedating properties in hospitalized adult patients.	2004 Mar 24	15040803
[Diphenhydramin-overdose: anticholinergic symptoms, EEG-findings in the course and drug treatment of a gerontopsychiatric patient].	2004 Nov	15570534
Effects of zolpidem and temazepam on driving ability.	2004 Nov	15511711
Alcohol and other drug use in later life.	2004 Oct	15532157
Strain differences in diazepam metabolism at its three metabolic sites in sprague-dawley, brown norway, dark agouti, and wistar strain rats.	2004 Sep	15319337
The effects of restricting publicly subsidised temazepam capsules on benzodiazepine use among injecting drug users in Australia.	2004 Sep 20	15377238
Effects of co-medicated drugs on cyclophosphamide bioactivation in human liver microsomes.	2005 Mar	15711186

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

Name

Type

Language

TEMAZEPAM

Official Name

English

TEMAZEPAM [WHO-DD]

Common 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

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 CIV

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