CAS 22316-47-8|clobazam|7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione|Clorepin|Urbadan|Clobazam|Urbanyl|Clobazam|7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazep...

General Information

Structure

Molecular Formula

C₁₆H₁₃ClN₂O₂

Molecular Mass

300.73962

Exact Mass

300.06655535

Charge

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

Canonic Smiles

Clc1ccc2c(c1)N(C(=O)CC(=O)N2C)c1ccccc1

Isomeric Smiles

Clc1cc2N(C(=O)CC(=O)N(c2cc1)C)c1ccccc1

Calculated Properties

JChem

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

Polarizability

30.81095

Polar Surface Area

40.62

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.14

LOG S

-3.26

Solubility (Water)

1.64e-01 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

clobazam

Synonyms

7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dioneClobazamClobazamclobazamHR 376MystanClobazepamH 4723LM 2717NSC 336279UrbadanFrisiumUrbanyl7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dioneFrizium

Brand Name

UrbadanClorepinUrbanylChlorepinFrisiumMystanFrisium, Urbanol, Onfi

IUPAC name

7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione

Names and Identifiers

Registration numbers

PubChem CID

2789

CAS Number

22316-47-8

PubChem SID

4650611516096369624893060

Chemspider ID

ATC CODE

DrugBank ID

Wikipedia Title

Unique Ingredient Identifier

CHEMBL

CHEBI ID

KEGG ID

MDL Number

EC Number

Registration numbers

Properties

Pharmacology Properties

Safety Information

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Drug Control

USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

German water hazard class

RTECS

DE9600000

MSDS Link

Download link

Controlled Substance, -20°C Freezer

Product Information

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00349

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]

Wikipedia

Clobazam

Sigma Aldrich

C8414

Biochem/physiol Actions
Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

TRC

C582500

Benzodiazepine psychotherapeutic agent. Clobazam (CLB) has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant. Controlled substance (depressant).

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• : 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

• Freche C: [Study of an anxiolytic, clobazam, in otorhinolaryngology in psychosomatic pharyngeal manifestations] Sem Hop Ther. 1975 Apr;51(4):261-3. Pubmed

• Kilpatrick C, Bury R, Fullinfaw R, Moulds R: Clobazam in the treatment of epilepsy. Clin Exp Neurol. 1987;23:139-44. Pubmed

• Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1979)

• Gastaut, H., et al.: Epilepsia, 20, 437 (1979)

• Munn, R., et al.: Pediatr. Neurol. 9, 465 (1979)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

IUPAC Traditional name

clobazam

Synonyms

Brand Name

UrbadanClorepinUrbanylChlorepinFrisiumMystanFrisium, Urbanol, Onfi

IUPAC name

7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-2,4-dione

Registration numbers

PubChem CID

2789

CAS Number

22316-47-8

PubChem SID

4650611516096369624893060

Chemspider ID

ATC CODE

DrugBank ID

Wikipedia Title

Unique Ingredient Identifier

CHEMBL

CHEBI ID

KEGG ID

MDL Number

EC Number

Molecule Details

DB00349

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

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]

Wikipedia

Clobazam

Sigma Aldrich

C8414

Biochem/physiol Actions
Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

TRC

C582500

Benzodiazepine psychotherapeutic agent. Clobazam (CLB) has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant. Controlled substance (depressant).

References

PubChem Literature

From Data Sources

• 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

• : 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

• Freche C: [Study of an anxiolytic, clobazam, in otorhinolaryngology in psychosomatic pharyngeal manifestations] Sem Hop Ther. 1975 Apr;51(4):261-3. Pubmed

• Kilpatrick C, Bury R, Fullinfaw R, Moulds R: Clobazam in the treatment of epilepsy. Clin Exp Neurol. 1987;23:139-44. Pubmed

• Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1979)

• Gastaut, H., et al.: Epilepsia, 20, 437 (1979)

• Munn, R., et al.: Pediatr. Neurol. 9, 465 (1979)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Safety Information

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Drug Control

USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

German water hazard class

RTECS

DE9600000

MSDS Link

Download link

Controlled Substance, -20°C Freezer

Product Information

Certificate of Analysis

Download link

Molecule

ID:233