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| Name | Temazepam | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00231 (APRD00676) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Type | small molecule | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Groups | approved | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | A benzodiazepine that acts as a gamma-aminobutyric acid modulator and anti-anxiety agent. [PubChem] |
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| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
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| Synonyms |
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| Brand names |
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| Brand name mixtures | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| CAS number | 846-50-4 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 300.74 Monoisotopic: 300.066555377 |
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| Chemical Formula | C16H13ClN2O2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=SEQDDYPDSLOBDC-UHFFFAOYSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI |
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
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| IUPAC Name |
7-chloro-3-hydroxy-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
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| SMILES |
CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1
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| Mass Spec | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Pharmacology | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Indication | For the short-term treatment of insomnia (generally 7-10 days). | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | 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. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Absorption | Well absorbed, minimal first-pass metabolism. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Protein binding | 96% | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Metabolism |
Hepatic. Temazepam is completely metabolized through conjugation prior to excretion. The major metabolite is the O-conjugate of temazepam (90%).
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| Route of elimination | Temazepam was completely metabolized through conjugation prior to excretion; 80% to 90% of the dose appeared in the urine. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Half life | 10-20 hours | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Toxicity | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Pathways | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State | solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point | 119-121oC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Synthesis Reference | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| General Reference |
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| PDB Entries | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| FDA label | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| MSDS | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Drug Interactions | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Targets |
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1. Gamma-aminobutyric-acid receptor subunit alpha-1 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P14867  Gene: GABRA1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
2. Gamma-aminobutyric-acid receptor subunit alpha-2 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P47869 Gene: GABRA2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
3. Gamma-aminobutyric-acid receptor subunit alpha-3 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P34903 Gene: GABRA3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
4. Gamma-aminobutyric-acid receptor subunit alpha-4 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P48169 Gene: GABRA4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
5. Gamma-aminobutyric-acid receptor subunit alpha-5 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P31644 Gene: GABRA5 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
6. Gamma-aminobutyric-acid receptor subunit alpha-6 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: Q16445 Gene: GABRA6 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
7. Gamma-aminobutyric-acid receptor subunit beta-1 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P18505 Gene: GABRB1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
8. Gamma-aminobutyric-acid receptor subunit beta-2 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P47870 Gene: GABRB2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
9. Gamma-aminobutyric-acid receptor subunit beta-3 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P28472 Gene: GABRB3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
10. Gamma-aminobutyric acid receptor subunit gamma-1 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: Q8N1C3 Gene: GABRG1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
11. Gamma-aminobutyric acid receptor subunit gamma-2 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P18507 Gene: GABRG2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
12. Gamma-aminobutyric acid receptor subunit gamma-3 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: Q99928 Gene: GABRG3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
13. Gamma-aminobutyric acid receptor subunit delta Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: O14764 Gene: GABRD Protein Sequence: FASTA SNPs: SNPJam Report References:
14. Gamma-aminobutyric acid receptor subunit epsilon Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: P78334 Gene: GABRE Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
15. Gamma-aminobutyric acid receptor subunit pi Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. In the uterus, the function of the receptor appears to be related to tissue contractility. The binding of this pI subunit with other GABA(A) receptor subunits alters the sensitivity of recombinant receptors to modulatory agents such as pregnanolone Organism class: humanUniProt ID: O00591 Gene: GABRP Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
16. Gamma-aminobutyric-acid receptor subunit rho-1 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA receptor could play a role in retinal neurotransmission Organism class: humanUniProt ID: P24046 Gene: GABRR1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
17. Gamma-aminobutyric acid receptor subunit rho-2 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA receptor could play a role in retinal neurotransmission Organism class: humanUniProt ID: P28476 Gene: GABRR2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
18. Gamma-aminobutyric acid receptor subunit rho-3 Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel (By similarity) Organism class: humanUniProt ID: A8MPY1 Gene: GABRR3 Protein Sequence: FASTA SNPs: SNPJam Report References: 19. Gamma-aminobutyric acid receptor subunit theta Pharmacological action: yesActions: potentiator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: humanUniProt ID: Q9UN88 Gene: GABRQ Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
Pharmacological action: unknown
Actions: other Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme Organism class: humanUniProt ID: P30536 Gene: TSPO Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
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| Enzymes |
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Actions: substrate
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine UniProt ID: P33261Gene: CYP2C19 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide UniProt ID: P08684Gene: CYP3A4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics UniProt ID: P20813Gene: CYP2B6 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol) UniProt ID: P10632Gene: CYP2C8 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan UniProt ID: P11712Gene: CYP2C9 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References:
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This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.