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=C(C=C(Cl)C=C2)C(=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 202 Target ID: CHEMBL2093872 Sources: http://www.genome.jp/dbget-bin/www_bget?D00370	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018163s054lbl.pdf	Primary		Approved 8429	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
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 84 UGT2B7 146

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/20111869/	yes
UGT2B7 157	inhibitor 3277 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
Oral temazepam.	2001 Jan 27	11213334
Culture of porcine hepatocytes: the dogma of exogenous matrix revisited.	2001 Jul	11493275
Anxiety in patients having caesarean section under regional anaesthesia: a questionnaire and pilot study.	2001 Oct	15321585
Use of night-time benzodiazepines in an elderly inpatient population.	2002 Apr	11975692
Digit loss following misuse of temazepam.	2002 Apr 15	12041634
Insomnia. Diagnosis and management.	2002 Nov	12471955
Analysis of homotropic and heterotropic cooperativity of diazepam oxidation by CYP3A4 using site-directed mutagenesis and kinetic modeling.	2003 Jan 1	12464248
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 May 25	12705973
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
A near-fatal overdose of carisoprodol (SOMA): case report.	2004	15214630
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
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
Strain differences in diazepam metabolism at its three metabolic sites in sprague-dawley, brown norway, dark agouti, and wistar strain rats.	2004 Sep	15319337

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 `Fri Dec 15 15:25:51 GMT 2023` Edited by `admin` on `Fri Dec 15 15:25:51 GMT 2023`
Record UNII	CHB1QD2QSS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEMAZEPAM

Official 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 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