Clobazam

Identification

Name

Clobazam

Accession Number

DB00349

Description

Clobazam belongs to the 1,5-benzodiazepine class of drugs and is expected to have a better side-effect profile compared to older 1,4-benzodiazepines. It has been marketed as an anxiolytic since 1975 and an anticonvulsant since 1984. The oral preparation was FDA approved on October 21, 2011. An oral suspension is expected to be available in 2013.

Type

Small Molecule

Groups

Approved, Illicit

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Clobazam (DB00349)

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Weight

Average: 300.74
Monoisotopic: 300.066555377

Chemical Formula

C₁₆H₁₃ClN₂O₂

Synonyms

• 1-phenyl-5-methyl-8-chloro-1,2,4,5-tetrahydro-2,4-dioxo-3H-1,5-benzodiazepine
• 7-Chloro-1-methyl-5-phenyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione
• Clobazam
• Clobazamum

External IDs

• H 4723
• H-4723
• HR 376
• HR-376
• LM 2717
• LM-2717

Pharmacology

Indication

For treatment and management of epilepsy and seizures associated with Lennox-Gastaut syndrome, a difficult-to-treat form of childhood epilepsy.

Associated Conditions

• Epilepsies

Contraindications & Blackbox Warnings

Learn about our commercial Contraindications & Blackbox Warnings data.

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Pharmacodynamics

Similar to other benzodiazepines, clobazam binds to the interface of the α and γ2-subunit of the GABA-A receptor. However, it is considered a partial agonist to GABA-A receptors which sets clobazam apart from 1,4-benzodiazepines which are full agonist. The significance of this difference is that one may experience less sedation with clobazam than with other benzodiazepines. Unlike the endogenous GABA ligand, clobazam binds allosterically to the GABA receptor to increase the frequency of the chloride channel opening and membrane permeability to chloride ions. Pharmacodynamic tolerance has been demonstrated in animal models.

Mechanism of action

Clobazam binds at distinct binding sites associated with the chloride ionopore at the post-synaptic GABA receptor. These GABA receptors are in various locations in the CNS (limbic, reticular formation) and clobazam increases the duration of time for which the chloride ionopore is open. As a result, hyper polarization and stabilization of the membrane occur as the post-synaptic inhibitory effect of GABA is enhanced.

Target	Actions	Organism
AGABA(A) Receptor	positive allosteric modulator	Humans
AGABA(A) Receptor Benzodiazepine Binding Site	ligand	Humans

Absorption

After oral administration of clobazam, it is almost completely absorbed (87% of dose). Bioavailability relative to solution was almost at 100%. Food does not affect absorption. Tmax = 1-3 hours.

Volume of distribution

Vdss = 100 L. This high volume of distribution suggests extensive distribution to body tissues.

Protein binding

Clobazam is the primary circulating entity in the serum and is highly protein-bound (80-90%).

Metabolism

Clobazam is extensively metabolized in the liver via N-demethylation and hydroxylation to form two major metabolites, N-desmethylclobazam (norclobazam) and 4'-hydroxyclobazam, respectively. N-desmethylclobazam (norclobazam) retains pharmacological activity. Norclobazam is one-fourth the potency of clobazam. The main enzyme that facilitates the process of N-demethylation is CYP3A4, and to a lesser extent by CYP2C19 and CYP2B6. Norclobazam itself is also metabolized via hydroxylation, primarily by CYP2C19. The formation of 4'-hydroxyclobazam is facilitated by CYP2C18 and CYP2C19. A factor in determining extent of metabolism is the genetic profile of the individual patient as CYP2C19 is a polymorphic enzyme.

Hover over products below to view reaction partners

• Clobazam
  • norclobazam
  • 4'-hydroxyclobazam

Route of elimination

Clobazam is eliminated via the urine (~94%) as metabolites.

Half-life

The mean elimination half life of an oral dose of clobazam 40 mg is 32 hours. It's main metabolite, norclobazam, as a half life of 57 hours. The half life in adult patients with epilepsy are higher than those that are healthy.

Clearance

Median estimated clearance = 2.49 L/h

Adverse Effects

Learn about our commercial Adverse Effects data.

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Toxicity

The most common adverse effects include somnolence, pyrexia, upper respiratory tract infection, and lethargy.

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Cytochrome P450 2C19	CYP2C19*2	(A;A) / (A;G)	G > A/C	ADR Directly Studied	Patients with this genotype have reduced metabolism of clobazam.	Details
Cytochrome P450 2C19	CYP2C19*2A	Not Available	681G>A	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*2B	Not Available	681G>A	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*3	Not Available	636G>A	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*4	Not Available	1A>G	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*5	Not Available	1297C>T	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*6	Not Available	395G>A	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*7	Not Available	19294T>A	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*22	Not Available	557G>C / 991A>G	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*24	Not Available	99C>T / 991A>G  … show all	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details
Cytochrome P450 2C19	CYP2C19*35	Not Available	12662A>G	ADR Inferred	Clobazem is metabolized into N-desmethylclobazem (NCLB) mostly by CYP3A4. NCLB is primarily metabolized by 2C19. Those with one 2C19*2 allele mutation (1*/2*) are intermediate metabolizers of NCLB. Those with two (2*/2*) mutations will metabolize NCLB poorly in comparisone to extensive metabolizers (1*/1*). Levels of NCLB can be five times higher in poor metabolizers, and two times higher in intermediate metabolizers as compared to individuals who are extensive metabolizers. The safety and efficacy of clobazem may be affected by polymorphic expression of CYP2C19*2.	Details

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Unlock Additional Data
Abacavir	Clobazam may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abametapir	The serum concentration of Clobazam can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Clobazam can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be increased when combined with Clobazam.
Abiraterone	The metabolism of Clobazam can be decreased when combined with Abiraterone.
Acalabrutinib	The metabolism of Acalabrutinib can be increased when combined with Clobazam.
Acarbose	Acarbose may decrease the excretion rate of Clobazam which could result in a higher serum level.
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Clobazam.
Aceclofenac	Aceclofenac may decrease the excretion rate of Clobazam which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Clobazam which could result in a higher serum level.

Additional Data Available

Extended Description
Extended Description
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Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
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Evidence Level
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Food Interactions

• Avoid alcohol. Alcohol increases clobazam absorption by 50%.
• Take with or without food. The absorption is unaffected by food.

Products

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Product Images

International/Other Brands

Aedon (Sanofi-Aventis) / Castilium (Sanofi-Aventis) / Clobam (Square) / Clobamax (Sherfarma) / Frisium (Sanofi-Aventis) / Grifoclobam (Chile) / Mystan (Dainippon Sumitomo) / Noiafren (Sanofi Aventis) / Sederlona / Urbanil (Sanofi-Aventis) / Urbanol (Sanofi-Aventis) / Urbanyl (Sanofi-Aventis) / Venium (Hudson)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Clobazam-10	Tablet		Oral	Pro Doc Limitee	2003-12-09	2017-05-05
Frisium Tab 10mg	Tablet		Oral	Hoechst Canada Inc.	1991-12-31	1996-08-29
Frisium Tablet 10mg	Tablet		Oral	Lundbeck Pharmaceuticals Llc	1997-03-24	2018-08-31
Frisium Tablets 10mg	Tablet		Oral	Hoechst Roussel Canada Inc.	1994-12-31	1999-08-11
Onfi	Tablet	10 mg/1	Oral	Lundbeck Pharmaceuticals Llc	2013-12-10	Not applicable
Onfi	Tablet	5 mg/1	Oral	Lundbeck Inc.	2011-10-21	2011-10-31
Onfi	Suspension	2.5 mg/1mL	Oral	Lundbeck Pharmaceuticals Llc	2012-12-14	Not applicable
Onfi	Tablet	20 mg/1	Oral	Lundbeck Inc.	2011-10-21	2011-10-31
Onfi	Tablet	20 mg/1	Oral	Lundbeck Pharmaceuticals Llc	2013-12-10	Not applicable
Onfi	Tablet	10 mg/1	Oral	Lundbeck Inc.	2011-10-21	2011-10-31

Additional Data Available

Application Number
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Product Code
Product Code
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Apo-clobazam	Tablet		Oral	Apotex Corporation	2001-11-28	Not applicable
Clobazam	Tablet	10 mg/1	Oral	Cadila Healthcare Limited	2018-10-22	Not applicable
Clobazam	Suspension	2.5 mg/1mL	Oral	Taro Pharmaceuticals U.S.A., Inc.	2019-04-16	Not applicable
Clobazam	Tablet	10 mg/1	Oral	Taro Pharmaceuticals U.S.A., Inc.	2018-10-22	Not applicable
Clobazam	Tablet	20 mg/1	Oral	Camber Pharmaceuticals, Inc.	2018-10-22	Not applicable
Clobazam	Suspension	2.5 mg/1mL	Oral	Lupin Pharmaceuticals, Inc.	2019-02-13	Not applicable
Clobazam	Suspension	2.5 mg/1mL	Oral	Northstar RxLLC	2020-05-01	Not applicable
Clobazam	Tablet	20 mg/1	Oral	Ascend Laboratories, LLC	2019-09-07	Not applicable
Clobazam	Tablet	10 mg/1	Oral	Northstar RxLLC	2018-11-12	Not applicable
Clobazam	Tablet	10 mg/1	Oral	Upsher-Smith Laboratories, LLC	2018-10-22	Not applicable

Additional Data Available

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Product Code
Product Code
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Categories

ATC Codes

N05BA09 — Clobazam

• N05BA — Benzodiazepine derivatives
• N05B — ANXIOLYTICS
• N05 — PSYCHOLEPTICS
• N — NERVOUS SYSTEM

Drug Categories

• Anti-Anxiety Agents
• Anticonvulsants
• Benzazepines
• Benzodiazepines and benzodiazepine derivatives
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP2B6 Substrates
• Cytochrome P-450 CYP2C18 Substrates
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (moderate)
• Cytochrome P-450 CYP3A Inducers
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inducers
• Cytochrome P-450 CYP3A4 Inducers (strength unknown)
• Cytochrome P-450 CYP3A4 Inducers (weak)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs that are Mainly Renally Excreted
• GABA Agents
• GABA Agonists
• GABA-A Receptor Agonists
• Heterocyclic Compounds, Fused-Ring
• Nervous System
• Neurotransmitter Agents
• P-glycoprotein substrates
• Psycholeptics
• Psychotropic Drugs
• Tranquilizing Agents

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

Not Available

Direct Parent

Benzodiazepines

Alternative Parents

1,4-diazepines / Benzene and substituted derivatives / Aryl chlorides / 1,3-dicarbonyl compounds / Tertiary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives

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Substituents

1,3-dicarbonyl compound / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Benzodiazepine / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / Lactam / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organochloride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Para-diazepine / Tertiary carboxylic acid amide

show 13 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound, 1,4-benzodiazepinone (CHEBI:31413)

Chemical Identifiers

UNII

2MRO291B4U

CAS number

22316-47-8

InChI Key

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

IUPAC Name

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

SMILES

CN1C2=C(C=C(Cl)C=C2)N(C2=CC=CC=C2)C(=O)CC1=O

References

Synthesis Reference

Hauptmann, K.H., Weber, K.-H., Zeile, K., Danneberg, P. and Giesemann, R.; South African Patent 68/0803; February 7,1968; assigned to Boehringer lngelheim GmbH, Germany.

General References

1. Freche C: [Study of an anxiolytic, clobazam, in otorhinolaryngology in psychosomatic pharyngeal manifestations]. Sem Hop Ther. 1975 Apr;51(4):261-3. [PubMed:5777]
2. Authors unspecified: 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:2044502]
3. 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:2106335]
4. Kilpatrick C, Bury R, Fullinfaw R, Moulds R: Clobazam in the treatment of epilepsy. Clin Exp Neurol. 1987;23:139-44. [PubMed:3117456]
5. Giarratano M, Standley K, Benbadis SR: Clobazam for treatment of epilepsy. Expert Opin Pharmacother. 2012 Feb;13(2):227-33. doi: 10.1517/14656566.2012.647686. Epub 2012 Jan 13. [PubMed:22242724]
6. Yang LP, Scott LJ: Clobazam : in patients with Lennox-Gastaut syndrome. CNS Drugs. 2012 Nov;26(11):983-91. doi: 10.1007/s40263-012-0007-0. [PubMed:23034582]
7. Walzer M, Bekersky I, Blum RA, Tolbert D: Pharmacokinetic drug interactions between clobazam and drugs metabolized by cytochrome P450 isoenzymes. Pharmacotherapy. 2012 Apr;32(4):340-53. doi: 10.1002/j.1875-9114.2012.01028.x. Epub 2012 Mar 15. [PubMed:22422635]

External Links

Human Metabolome Database

HMDB0014493

KEGG Drug

D01253

PubChem Compound

2789

PubChem Substance

46506115

ChemSpider

2687

BindingDB

50247888

RxNav

21241

ChEBI

31413

ChEMBL

CHEMBL70418

ZINC

ZINC000000001175

Therapeutic Targets Database

DAP000672

PharmGKB

PA10888

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Clobazam

AHFS Codes

• 28:12.08 — Benzodiazepines

FDA label

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MSDS

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Anxiety / Epilepsies	1
4	Unknown Status	Treatment	Epilepsies	2
4	Unknown Status	Treatment	Refractory Epilepsy	1
3	Completed	Basic Science	Back Pain Lower Back	1
3	Completed	Treatment	Epilepsies / Epilepsy, Generalized / Seizures	1
3	Completed	Treatment	Lennox-Gastaut Syndrome (LGS)	1
3	Completed	Treatment	Pain	1
3	Terminated	Treatment	Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia	1
3	Terminated	Treatment	Dravet Syndrome	1
3	Terminated	Treatment	Epilepsia Partialis Continua / Epilepsies / Kojewnikov's Epilepsy	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Solution	Oral	2.5 mg/1mL
Suspension	Oral	2.5 mg/1mL
Tablet	Oral	5 mg
Tablet	Oral	10 MG
Tablet	Oral	20 mg
Tablet	Oral
Tablet	Oral	10 mg/1
Tablet	Oral	20 mg/1
Tablet	Oral	5 mg/1
Film	Oral	10 mg/1
Film	Oral	20 mg/1
Film	Oral	5 mg/1
Suspension	Oral	0.25 g

Prices

Unit description	Cost	Unit
Apo-Clobazam 10 mg Tablet	0.23USD	tablet
Novo-Clobazam 10 mg Tablet	0.23USD	tablet
Pms-Clobazam 10 mg Tablet	0.23USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
Unlock Additional Data
US8603514	No	2013-12-10	2024-04-03
US8765167	No	2014-07-01	2024-02-20

Additional Data Available

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Filed On
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The date on which a patent was filed with the relevant government.
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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	180-182	Hauptmann, K.H., Weber, K.-H., Zeile, K., Danneberg, P. and Giesemann, R.; South African Patent 68/0803; February 7,1968; assigned to Boehringer lngelheim GmbH, Germany.
water solubility	188 mg/L	Not Available
logP	2.12	HENCZI,M ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	0.164 mg/mL	ALOGPS
logP	2.14	ALOGPS
logP	2.55	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å2	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.3 m3·mol-1	ChemAxon
Polarizability	30.07 Å3	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.99
Blood Brain Barrier	+	0.9904
Caco-2 permeable	+	0.7487
P-glycoprotein substrate	Non-substrate	0.5733
P-glycoprotein inhibitor I	Non-inhibitor	0.5462
P-glycoprotein inhibitor II	Non-inhibitor	0.9204
Renal organic cation transporter	Non-inhibitor	0.7373
CYP450 2C9 substrate	Non-substrate	0.7058
CYP450 2D6 substrate	Non-substrate	0.8607
CYP450 3A4 substrate	Substrate	0.6871
CYP450 1A2 substrate	Non-inhibitor	0.6829
CYP450 2C9 inhibitor	Non-inhibitor	0.5296
CYP450 2D6 inhibitor	Non-inhibitor	0.8908
CYP450 2C19 inhibitor	Non-inhibitor	0.5791
CYP450 3A4 inhibitor	Inhibitor	0.7008
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5308
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.7846
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	1.7313 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9896
hERG inhibition (predictor II)	Non-inhibitor	0.8651

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

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Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-0pb9-6392000000-a76f30f353b3407df0c6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4i-0090000000-3b46d60abcc8dfacf4d8
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0udi-0019000000-71512d7a18cf60430dd9
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-0092000000-e687a1e3760fb870dbc9
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-0090000000-d450ded1f22039f00b63
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0ab9-0190000000-e4211cbc2957a587e3d3
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-05fr-0590000000-51f4fa0445c2d047ef6b
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0g4j-1960000000-a89e1c91bfa7b974be48
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-014j-4920000000-93c0877b3acf519d2b98
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-016u-7900000000-bc29714be08b6ae4120b
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0hi6-9600000000-7c6a3974d95a0015757e

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Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38