Drug/Small Molecule:
temazepam

2D structure

Overview

Generic Names: Hydroxydiazepam; Methyloxazepam; N-Methyloxazepam; Oxydiazepam
IUPAC Name: 7-chloro-3-hydroxy-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
Trade Names: Apo-Temazepam; Cerepax; Crisonar; Euhypnos; Euipnos; Gelthix; Levanxene; Levanxol; Levanzene; Mabertin; Normison; Novo-Temazepam; Perdorm; Planum; Remestan; Restoril; Signopam; Temaz
PharmGKB Accession Id: PA451608

Description

A benzodiazepine that acts as a gamma-aminobutyric acid modulator and anti-anxiety agent. [PubChem]

Indication

For the short-term treatment of insomnia (generally 7-10 days).

ATC Therapeutic Category

  • N05CD:Benzodiazepine derivatives

Pharmacology and Interactions

Mechanism Of 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.

Pharmacology

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.

Food Interactions

Avoid alcohol. Avoid avocado. Avoid excessive quantities of coffee or tea (Caffeine).

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. Temazepam is completely metabolized through conjugation prior to excretion. The major metabolite is the O-conjugate of temazepam (90%).

Protein Binding

96%

Absorption

Well absorbed, minimal first-pass metabolism.

Half Life

10-20 hours

Chemical Properties

Chemical Formula:

C16H13ClN2O2

SMILES Code:

CN1C2=C(C=C(C=C2)Cl)C(=N[C@@H](C1=O)O)C3=CC=CC=C3

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

300.74 / 300.0666

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
No phenotype data No genotype data No literature annotations Not annotated
ACBD3
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  • PD
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Pathways
No phenotype data No genotype data No literature annotations Not annotated
BZRAP1
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Pathways
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2C19
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  • PK
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Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
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  • PK
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
DBI
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
GABRA1
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  • PD
  • PK
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Publications, Pathways
No phenotype data No genotype data Literature annotations available Not annotated
GABRB2
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  • PD
  • PK
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Publications, Pathways
No phenotype data No genotype data Literature annotations available Not annotated
GABRG2
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  • PD
  • PK
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Publications, Pathways
No phenotype data No genotype data No literature annotations Not annotated
SLC25A4
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  • PD
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Pathways
No phenotype data Genotype Data Available No literature annotations Not annotated
SLC32A1
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  • PD
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Pathways
No phenotype data Genotype Data Available Literature annotations available Not annotated
SLC6A1
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  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
SLC6A11
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  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
SLC6A12
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  • PD
  • PK
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Pathways
No phenotype data No genotype data No literature annotations Not annotated
SLC6A13
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  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
TSPO
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Pathways
Phenotype data available Genotype Data Available Literature annotations available Not annotated
UGT2B7
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  • PK
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Publications
No phenotype data No genotype data No literature annotations Not annotated
VDAC1
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Pathways

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

clozapine Increased risk of toxicity
ethotoin Possible increased levels of the hydantoin, decrease of benzodiazepine
fosphenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine
kava Kava increases the effect of the benzodiazepine
mephenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine
phenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Anxiety Disorders
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  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
Epilepsy
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  • PD
  • PK
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Pathways
No phenotype data No genotype data Literature annotations available Not annotated
Panic Disorder
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  • PD
  • PK
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Pathways

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00231
KEGG Drug ID:
D00370
PubChem Compound ID:
5391
PubChem Substance ID:
156664

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
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