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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 of TEMAZEPAM

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

Molecular Formula C16H13ClN2O2
Molecular Weight 300.7402
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

3.51993594E11
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
Anxiety in patients having caesarean section under regional anaesthesia: a questionnaire and pilot study.
2001 Oct
Recent trends in benzodiazepine use by injecting drug users in Victoria and Tasmania.
2002 Dec
Hypnotic medication in the aftermath of trauma.
2002 Dec
Long-term effects of and physiological responses to nitrous oxide gas treatment during alcohol withdrawal: a double-blind, placebo-controlled trial.
2002 Dec
A combination of intrathecal morphine and remifentanil anesthesia for fast-track cardiac anesthesia and surgery.
2002 Dec
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
Mechanism of increased dissolution of diazepam and temazepam from polyethylene glycol 6000 solid dispersions.
2002 Dec 5
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
Comparative study of the metabolism of drug substrates by human cytochrome P450 3A4 expressed in bacterial, yeast and human lymphoblastoid cells.
2002 Nov
Insomnia. Diagnosis and management.
2002 Nov
Analytical developments in toxicological investigation of drug-facilitated sexual assault.
2003 Aug
Improving daytime sleep with temazepam as a countermeasure for shift lag.
2003 Feb
Biomarkers for the effects of benzodiazepines in healthy volunteers.
2003 Jan
Temazepam, but not zolpidem, causes orthostatic hypotension in astronauts after spaceflight.
2003 Jan
Acute pharmacological effects of temazepam, diphenhydramine, and valerian in healthy elderly subjects.
2003 Jun
Case report: severe mercuric sulphate poisoning treated with 2,3-dimercaptopropane-1-sulphonate and haemodiafiltration.
2003 Jun
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
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
[Comparative kinetics of 3-hydroxyphenazepam and its metabolism during transdermal and intravenous administration].
2003 May-Jun
Effects of after-midnight intake of zolpidem and temazepam on driving ability in women with non-organic insomnia.
2003 Nov
Chiral separations using polymeric surfactants and polyelectrolyte multilayers in open-tubular capillary electrochromatography.
2003 Nov 15
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
The interactive effects of alcohol and temazepam on P300 and reaction time.
2003 Oct
Use of poly(sodium oleyl-L-leucylvalinate) surfactant for the separation of chiral compounds in micellar electrokinetic chromatography.
2003 Sep
Neurobehavioural performance effects of daytime melatonin and temazepam administration.
2003 Sep
Toward evidence-based prescribing at end of life: a comparative review of temazepam and zolpidem for the treatment of insomnia.
2003 Sep-Oct
Pharmacokinetics and drug interactions of the sedative hypnotics.
2003 Winter
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
[Signopam treatment of insomnia in patients with somatic pathology].
2004
A near-fatal overdose of carisoprodol (SOMA): case report.
2004
Residual effects of hypnotics: epidemiology and clinical implications.
2004
Changes in fatalities due to overdose of anxiolytic and sedative drugs in the UK (1983-1999).
2004
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
Zolpidem is not superior to temazepam with respect to rebound insomnia: a controlled study.
2004 Aug
Psychological treatment for insomnia in the regulation of long-term hypnotic drug use.
2004 Feb
CNS effects of sumatriptan and rizatriptan.
2004 Jan
Monitoring of drugs and metabolites in whole blood by restricted-access solid-phase microextraction coupled to liquid chromatography-mass spectrometry.
2004 Jan 30
Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis.
2004 Jul
Sleep-inducing pharmaceuticals: a comparison of melatonin, zaleplon, zopiclone, and temazepam.
2004 Jun
Evaluation of actigraphy and automated telephoned questionnaires to assess hypnotic effects in insomnia.
2004 Mar
An assessment of quality of sleep and the use of drugs with sedating properties in hospitalized adult patients.
2004 Mar 24
[Diphenhydramin-overdose: anticholinergic symptoms, EEG-findings in the course and drug treatment of a gerontopsychiatric patient].
2004 Nov
Effects of zolpidem and temazepam on driving ability.
2004 Nov
Alcohol and other drug use in later life.
2004 Oct
'Hypnotic' prescription patterns in a large managed-care population.
2004 Sep
Strain differences in diazepam metabolism at its three metabolic sites in sprague-dawley, brown norway, dark agouti, and wistar strain rats.
2004 Sep
The effects of restricting publicly subsidised temazepam capsules on benzodiazepine use among injecting drug users in Australia.
2004 Sep 20
Effects of co-medicated drugs on cyclophosphamide bioactivation in human liver microsomes.
2005 Mar
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 Jun 25 20:57:57 UTC 2021
Edited
by admin
on Fri Jun 25 20:57:57 UTC 2021
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
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
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 Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
LIVERTOX 931
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
NDF-RT N0000175694
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
DEA NO. 2925
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
NDF-RT N0000007542
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
NCI_THESAURUS C1012
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
WHO-VATC QN05CD07
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C29488
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
USP_CATALOG
1643408
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY USP-RS
RXCUI
10355
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY RxNorm
CAS
846-50-4
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
PUBCHEM
5391
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
212-688-1
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
DRUG BANK
DB00231
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
MESH
D013693
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
EPA CompTox
846-50-4
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
WIKIPEDIA
TEMAZEPAM
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
DRUG CENTRAL
2585
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
INN
2753
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
LACTMED
Temazepam
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
MERCK INDEX
M10545
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY Merck Index
FDA UNII
CHB1QD2QSS
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL967
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
IUPHAR
7300
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
EVMPD
SUB10880MIG
Created by admin on Fri Jun 25 20:57:57 UTC 2021 , Edited by admin on Fri Jun 25 20:57:57 UTC 2021
PRIMARY
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