U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of TEMAZEPAM

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
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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Restoril

Approved Use

Restoril™ (temazepam) is indicated for the short-term treatment of insomnia (generally 7 to 10 days).

Launch Date

1981
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
865 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1800 ng × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.8 h
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
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
4%
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%
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

Doses

DosePopulationAdverse events​
26 mg single, intravenous
Dose: 26 mg
Route: intravenous
Route: single
Dose: 26 mg
Sources:
healthy, 18 - 24 years
Health Status: healthy
Age Group: 18 - 24 years
Sex: M+F
Sources:
40 mg single, oral
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Citalopram and sexual side effects of selective serotonin reuptake inhibitors.
1999 May
High-speed liquid chromatography/tandem mass spectrometry using a monolithic column for high-throughput bioanalysis.
2001
The effect of single oral doses of zopiclone on nocturnal melatonin secretion in healthy male volunteers.
2001 May
The use of vitreous humor as an alternative to whole blood for the analysis of benzodiazepines.
2001 May
Treatment of insomnia in hospitalized patients.
2001 Nov
Experience with urine drug testing by the Correctional Service of Canada.
2001 Sep 15
Tolerability of hypnosedatives in older patients.
2002
Iatrogenic causes of falls in hospitalised elderly patients: a case-control study.
2002 Aug
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
Severe vein damage caused by Temezepam injecting.
2002 Feb
Behavioral treatment for chronic insomnia.
2002 Mar
Long term benzodiazepine use for insomnia in patients over the age of 60: discordance of patient and physician perceptions.
2002 May 8
Biomarkers for the effects of benzodiazepines in healthy volunteers.
2003 Jan
Interaction of alcohol and drugs in fatal poisonings.
2003 May
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
Effects of after-midnight intake of zolpidem and temazepam on driving ability in women with non-organic insomnia.
2003 Nov
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
[Benzodiazepines and forensic aspects].
2003 Nov-Dec
Use of poly(sodium oleyl-L-leucylvalinate) surfactant for the separation of chiral compounds in micellar electrokinetic chromatography.
2003 Sep
Pharmacokinetics and drug interactions of the sedative hypnotics.
2003 Winter
A near-fatal overdose of carisoprodol (SOMA): case report.
2004
Changes in fatalities due to overdose of anxiolytic and sedative drugs in the UK (1983-1999).
2004
An assessment of quality of sleep and the use of drugs with sedating properties in hospitalized adult patients.
2004 Mar 24
'Hypnotic' prescription patterns in a large managed-care population.
2004 Sep
Patents

Sample Use Guides

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
Curator's Comment: Temazepam alone caused an increase in twitch tension in lower concentrations, followed by complete depression in higher concentrations in rat phrenic nerve-hemidiaphragm preparation.
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
  • Download
Name Type Language
TEMAZEPAM
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
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
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
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
LIVERTOX NBK548556
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
NDF-RT N0000175694
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
DEA NO. 2925
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
NDF-RT N0000007542
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
NCI_THESAURUS C1012
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
WHO-VATC QN05CD07
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C29488
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
RXCUI
10355
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY RxNorm
CAS
846-50-4
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
PUBCHEM
5391
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-688-1
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
DRUG BANK
DB00231
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
SMS_ID
100000092289
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
MESH
D013693
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
NSC
246303
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID8021309
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
WIKIPEDIA
TEMAZEPAM
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
DRUG CENTRAL
2585
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
INN
2753
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
DAILYMED
CHB1QD2QSS
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
LACTMED
Temazepam
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
MERCK INDEX
m10545
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY Merck Index
FDA UNII
CHB1QD2QSS
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL967
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
RS_ITEM_NUM
1643408
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
IUPHAR
7300
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
EVMPD
SUB10880MIG
Created by admin on Fri Dec 15 15:25:52 GMT 2023 , Edited by admin on Fri Dec 15 15:25:52 GMT 2023
PRIMARY
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