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| Name | Clobazam | ||||||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00349 (APRD00307) | ||||||||||||||||||||||||||||||||||||||||||
| Type | small molecule | ||||||||||||||||||||||||||||||||||||||||||
| Groups | illicit, approved | ||||||||||||||||||||||||||||||||||||||||||
| Description | Clobazam is a drug which is a benzodiazepine derivative. It has been marketed as an anxiolytic since 1975 and an anticonvulsant since 1984. [Wikipedia] |
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| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
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| Synonyms | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Salts | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Brand mixtures | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| CAS number | 22316-47-8 | ||||||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 300.74 Monoisotopic: 300.066555377 |
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| Chemical Formula | C16H13ClN2O2 | ||||||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=CXOXHMZGEKVPMT-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||
| InChI |
InChI=1S/C16H13ClN2O2/c1-18-13-8-7-11(17)9-14(13)19(16(21)10-15(18)20)12-5-3-2-4-6-12/h2-9H,10H2,1H3
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| IUPAC Name |
7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione
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| SMILES |
CN1C2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)CC1=O
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| Mass Spec | show (11.4 KB) | ||||||||||||||||||||||||||||||||||||||||||
| Taxonomy | |||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic | ||||||||||||||||||||||||||||||||||||||||||
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| Pharmacology | |||||||||||||||||||||||||||||||||||||||||||
| Indication | For treatment and management of epilepsy and anxiety disorder. | ||||||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | Clobazam is a barbiturate used in combination with acetaminophen or aspirin and caffeine for its sedative and relaxant effects in the treatment of tension headaches, migraines, and pain. | ||||||||||||||||||||||||||||||||||||||||||
| Mechanism of action | Clobazam binds at a distinct binding site associated with a Cl- ionopore at the GABA-A receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is prolonged as a result. | ||||||||||||||||||||||||||||||||||||||||||
| Absorption | Bioavailability is 90%. | ||||||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Protein binding | 83% | ||||||||||||||||||||||||||||||||||||||||||
| Metabolism | Hepatic. Clobazam has two major metabolites: N-desmethyl-clobazam and 4'-hydroxyclobazam, the former of which is active. The demethylation is facilitated by CYP2C19, CYP3A4, and CYP2B6 and the 4'-hydroxyclobazam by CYP2C18 and CYP2C19. | ||||||||||||||||||||||||||||||||||||||||||
| Route of elimination | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Half life | 18 hours | ||||||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Toxicity | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Pathways | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Manufacturers | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Packagers | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Prices |
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational
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| Patents | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Properties | |||||||||||||||||||||||||||||||||||||||||||
| State | solid | ||||||||||||||||||||||||||||||||||||||||||
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| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| General Reference |
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| PDB Entries | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| FDA label | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| MSDS | show (57.5 KB) | ||||||||||||||||||||||||||||||||||||||||||
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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: |
| Enzymes |
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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: P08684![]() Gene: CYP3A4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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: P33261![]() Gene: 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics UniProt ID: P33260![]() Gene: CYP2C18 ![]() Protein 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: P20813![]() Gene: CYP2B6 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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