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

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
Citalopram and sexual side effects of selective serotonin reuptake inhibitors.	1999 May	10327919
High-speed liquid chromatography/tandem mass spectrometry using a monolithic column for high-throughput bioanalysis.	2001	11404848
Comparison of the rates of hydrolysis of lorazepam-glucuronide, oxazepam-glucuronide and tamazepam-glucuronide catalyzed by E. coli beta-D-glucuronidase using the on-line benzodiazepine screening immunoassay on the Roche/Hitachi 917 analyzer.	2001 Mar	11305436
Temazepam dangers.	2001 Mar 10	11303677
High-speed gradient parallel liquid chromatography/tandem mass spectrometry with fully automated sample preparation for bioanalysis: 30 seconds per sample from plasma.	2002	11992516
Severe vein damage caused by Temezepam injecting.	2002 Feb	11895033
Bio-compatible in-tube solid-phase microextraction capillary for the direct extraction and high-performance liquid chromatographic determination of drugs in human serum.	2002 Jul 19	12187987
Direct determination of benzodiazepines in biological fluids by restricted-access solid-phase microextraction.	2002 Mar 1	11924967
[Fatal outcome of poisoning with the benzodiazepines flunitrazepam and diazepam].	2002 Mar-Apr	12043441
CNS effects of sumatriptan and rizatriptan in healthy female volunteers.	2002 May	12100089
Comparative study of the metabolism of drug substrates by human cytochrome P450 3A4 expressed in bacterial, yeast and human lymphoblastoid cells.	2002 Nov	12487724
Insomnia. Diagnosis and management.	2002 Nov	12471955
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
Improving daytime sleep with temazepam as a countermeasure for shift lag.	2003 Feb	12602447
Analysis of homotropic and heterotropic cooperativity of diazepam oxidation by CYP3A4 using site-directed mutagenesis and kinetic modeling.	2003 Jan 1	12464248
Errors in performance testing: a comparison of ethanol and temazepam.	2003 Mar	12680738
Effects of after-midnight intake of zolpidem and temazepam on driving ability in women with non-organic insomnia.	2003 Nov	14607350
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
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
Residual effects of hypnotics: epidemiology and clinical implications.	2004	15089115
CNS effects of sumatriptan and rizatriptan.	2004 Jan	14687019
Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis.	2004 Jul	15252823
[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
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

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