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22316-47-8 molecular structure
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7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione

ChemBase ID: 233
Molecular Formular: C16H13ClN2O2
Molecular Mass: 300.73962
Monoisotopic Mass: 300.06655535
SMILES and InChIs

SMILES:
Clc1cc2N(C(=O)CC(=O)N(c2cc1)C)c1ccccc1
Canonical SMILES:
Clc1ccc2c(c1)N(C(=O)CC(=O)N2C)c1ccccc1
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
InChIKey:
CXOXHMZGEKVPMT-UHFFFAOYSA-N

Cite this record

CBID:233 http://www.chembase.cn/molecule-233.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione
IUPAC Traditional name
clobazam
Brand Name
Chlorepin
Clorepin
Frisium
Mystan
Urbadan
Urbanyl
Frisium, Urbanol, Onfi
Synonyms
7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione
Clobazepam
Frisium
Frizium
H 4723
HR 376
LM 2717
Mystan
NSC 336279
Urbadan
Urbanyl
clobazam
Clobazam
7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione
Clobazam
CAS Number
22316-47-8
EC Number
244-908-7
MDL Number
MFCD00079069
PubChem SID
24893060
46506115
160963696
PubChem CID
2789
CHEBI ID
31413
ATC CODE
N05BA09
CHEMBL
70418
Chemspider ID
2687
DrugBank ID
DB00349
KEGG ID
D01253
Unique Ingredient Identifier
2MRO291B4U
Wikipedia Title
Clobazam

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.068304  H Acceptors
H Donor LogD (pH = 5.5) 1.1145105 
LogD (pH = 7.4) -0.39646015  Log P 2.554376 
Molar Refractivity 80.2986 cm3 Polarizability 30.81095 Å3
Polar Surface Area 40.62 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.14  LOG S -3.26 
Solubility (Water) 1.64e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
188 mg/L expand Show data source
Chloroform expand Show data source
Apperance
N/AWhite Solid expand Show data source
Melting Point
162-164°C expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source
Storage Condition
Controlled Substance, -20°C Freezer expand Show data source
RTECS
DE9600000 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Drug Control
USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
90% expand Show data source
Excretion
Renal expand Show data source
Half Life
18 hours expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
83% expand Show data source
Legal Status
Schedule IV (US)
Class C (New Zealand)
Class C/Sch.4 (UK)
expand Show data source
Pregnancy Category
C (US) expand Show data source
US Licence
Clobazam expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00349 external link
Item Information
Drug Groups illicit; approved; investigational
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]
Indication For treatment and management of epilepsy and anxiety disorder.
Pharmacology 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.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption Bioavailability is 90%.
Half Life 18 hours
Protein Binding 83%
References
Freche C: [Study of an anxiolytic, clobazam, in otorhinolaryngology in psychosomatic pharyngeal manifestations] Sem Hop Ther. 1975 Apr;51(4):261-3. [Pubmed]
: Clobazam in treatment of refractory epilepsy: the Canadian experience. A retrospective study. Canadian Clobazam Cooperative Group. Epilepsia. 1991 May-Jun;32(3):407-16. [Pubmed]
Wildin JD, Pleuvry BJ, Mawer GE, Onon T, Millington L: Respiratory and sedative effects of clobazam and clonazepam in volunteers. Br J Clin Pharmacol. 1990 Feb;29(2):169-77. [Pubmed]
Kilpatrick C, Bury R, Fullinfaw R, Moulds R: Clobazam in the treatment of epilepsy. Clin Exp Neurol. 1987;23:139-44. [Pubmed]
External Links
Wikipedia
Sigma Aldrich - C8414 external link
Biochem/physiol Actions
Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.
Toronto Research Chemicals - C582500 external link
Benzodiazepine psychotherapeutic agent. Clobazam (CLB) has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant. Controlled substance (depressant).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Freche C: [Study of an anxiolytic, clobazam, in otorhinolaryngology in psychosomatic pharyngeal manifestations] Sem Hop Ther. 1975 Apr;51(4):261-3. Pubmed
  • • : Clobazam in treatment of refractory epilepsy: the Canadian experience. A retrospective study. Canadian Clobazam Cooperative Group. Epilepsia. 1991 May-Jun;32(3):407-16. Pubmed
  • • Wildin JD, Pleuvry BJ, Mawer GE, Onon T, Millington L: Respiratory and sedative effects of clobazam and clonazepam in volunteers. Br J Clin Pharmacol. 1990 Feb;29(2):169-77. Pubmed
  • • Kilpatrick C, Bury R, Fullinfaw R, Moulds R: Clobazam in the treatment of epilepsy. Clin Exp Neurol. 1987;23:139-44. Pubmed
  • • Gastaut, H., et al.: Epilepsia, 20, 437 (1979)
  • • Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1979)
  • • Munn, R., et al.: Pediatr. Neurol. 9, 465 (1979)
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PATENTS

PATENTS

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