CLOBAZAM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H13ClN2O2
Molecular Weight	300.74
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C2=CC=C(Cl)C=C2N(C3=CC=CC=C3)C(=O)CC1=O

InChI

InChIKey=CXOXHMZGEKVPMT-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H13ClN2O2
Molecular Weight	300.74
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202067s003,203993s003lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/cdi/clobazam.html; http://www.epilepsy.com/medications/clobazam https://www.ncbi.nlm.nih.gov/pubmed/?term=23318278

Clobazam belongs to the 1,5-benzodiazepine class of drugs with antiepileptic properties. It has been used to treat anxiety and epilepsy since 1970s. In the US clobazam was approved for marketing in October of 2011 for the adjunctive treatment of seizures associated with Lennox-Gastaut syndrome. It is also approved for adjunctive therapy for epilepsy in patients who have not responded to first-line drugs and in children who are refractory to first-line drugs. The mechanism of action for clobazam is not fully understood but is thought to involve what is known as potentiation of GABAergic neurotransmission resulting from binding at a benzodiazepine site at the GABA(A) receptor. Possible side effects: constipation, fever, drowsiness, sedation, ataxia, aggressive behavior, lethargy, drooling, and irritability. Other side effects include: urinary tract infection, pneumonia, cough, dysphagia, dysarthria, bronchitis, insomnia, fatigue, decreased appetite, and increased appetite.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22145708	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lennox-Gastaut syndrome 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202067s002,203993s002lbl.pdf	Secondary		Approved 8583	ONFI Approved Use Indicated for the adjunctive treatment of seizures associated with Lennox-Gastaut syndrome (LGS) in patients 2 years of age or older. Launch Date 2011

C_max

Value	Dose	Co-administered	Analyte	Population
641 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6529527/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CLOBAZAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
13741 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6529527/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		CLOBAZAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
36 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202067s005,203993s007lbl.pdf	30 mg 1 times / day unknown, oral dose: 30 mg route of administration: Oral experiment type: UNKNOWN co-administered:		CLOBAZAM plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/202067s005,203993s007lbl.pdf	30 mg 1 times / day unknown, oral dose: 30 mg route of administration: Oral experiment type: UNKNOWN co-administered:		CLOBAZAM plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg 2 times / day steady, oral Highest studied dose Dose: 80 mg, 2 times / day Route: oral Route: steady Dose: 80 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	Disc. AE: Somnolence, Depressed mood... Other AEs: Delirium... AEs leading to discontinuation/dose reduction: Somnolence (1 patient) Depressed mood (1 patient) Libido decreased (1 patient) Erectile dysfunction (1 patient) Insomnia (1 patient) Dysarthria (1 patient) Unsteady gait (1 patient) Dizziness (1 patient) Other AEs: Delirium (2 patients) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf
10 mg 2 times / day steady, oral Dose: 10 mg, 2 times / day Route: oral Route: steady Dose: 10 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	Disc. AE: Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf
15 mg 2 times / day steady, oral Dose: 15 mg, 2 times / day Route: oral Route: steady Dose: 15 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	Disc. AE: Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf
20 mg 2 times / day steady, oral Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	Disc. AE: Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (2 patients) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf
60 mg 2 times / day steady, oral Dose: 60 mg, 2 times / day Route: oral Route: steady Dose: 60 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	Disc. AE: Somnolence... AEs leading to discontinuation/dose reduction: Somnolence (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf
70 mg 2 times / day steady, oral Dose: 70 mg, 2 times / day Route: oral Route: steady Dose: 70 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf	Disc. AE: Dizziness, Somnolence... AEs leading to discontinuation/dose reduction: Dizziness (1 patient) Somnolence (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000MedR.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 substrate 1946 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8 1057 CYP2C19 2057 UGT1A1 246 UGT1A4 98 UGT1A6 136 UGT2B4 23 P-gp 1741	CYP2C19 1119 CYP2B6 776 P-gp 2052 OAT 5	UGT1A1 78

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 17.0	no
UGT1A1 303	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
UGT1A4 100	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
UGT1A6 171	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
UGT2B4 23	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0	no	yes (co-administration study) Comment: clobazam increased dextromethorphan cmax 90%, auc 59% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 16.0
UGT1A1 303	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 17.0	weak
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 9.0	weak	yes (co-administration study) Comment: clobazam decreased midazolam auc 27%, cmax 24% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 9.0

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 15.0	major	yes (co-administration study) Comment: ketoconazole increased clobazam auc 54%, no effect on cmax Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 15.0
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 15.0	minor
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 15.0	minor	yes (co-administration study) Comment: omeprazole increased clobazam auc 30-36%, no effect on cmax Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 15.0
OAT 5	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000ClinPharmR.pdf Page: 96.0	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 17.0	yes	yes (co-administration study) Comment: verapamil reduced clobazam transport >96% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/202067s000lbl.pdf Page: 17.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202067Orig1s000CrossR.pdf Page: 20.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31413	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31413
eMolecules	536528	https://www.emolecules.com/cgi-bin/more?vid=536528
ZINC	ZINC000000001175	http://zinc15.docking.org/substances/ZINC000000001175

PubMed

Title	Date	PubMed
The detection of sedatives in hair and nail samples using tandem LC-MS-MS.	2007-02-14	16707239
Clobazam.	2007-01	17199029
Stiripentol.	2007-01	17199026
[Epilepsy: which therapy in acute care?].	2006-12-08	17136662
Effects of some antiepileptics on septal-kindled seizures in rats.	2006-12	16938433
Oxidative stress in children receiving valproic acid.	2006-11	17095346
Quantification of benzodiazepines in whole blood and serum.	2006-11	16220317
Treatment in the pediatric emergency department is evidence based: a retrospective analysis.	2006-10-06	17022829
Effectiveness of clobazam as add-on therapy in children with refractory focal epilepsy.	2006-09	17057871
Landau-Kleffner syndrome is not an eponymic badge of ignorance.	2006-08	16806832
Eye rolling as a manifestation of clobazam toxicity in a child with epilepsy.	2006-07	16780634
Safety and efficacy of clobazam versus phenytoin-sodium in the antiepileptic drug treatment of solitary cysticercus granulomas.	2006-06	16804259
Benign angiopathy of the central nervous system associated with phenytoin intoxication.	2006-06	16376047
Clobazam as add-on therapy in children with epileptic encephalopathy.	2006-05	16736732
Stiripentol, a putative antiepileptic drug, enhances the duration of opening of GABA-A receptor channels.	2006-04	16650136
In vitro and in vivo inhibitory effect of stiripentol on clobazam metabolism.	2006-04	16415114
Abusive prescription of psychostimulants: a study of two cases.	2006-03	16566781
Anticonvulsant hypersensitivity syndrome to lamotrigine confirmed by lymphocyte stimulation in vitro.	2006-02	16505575
Pharmacological properties of GABAA receptors containing gamma1 subunits.	2006-02	16272224
Levetiracetam in idiopathic generalised epilepsy and porphyria cutanea tarda.	2006	17163270
[Epilepsy with electrical status epilepticus during slow sleep: diagnostic criteria and approaches to therapy].	2006	16737153
Molecular regulation of glutamate and GABA transporter proteins by clobazam during epileptogenesis in Fe(+++)-induced epileptic rats.	2005-12-14	16274841
Screening method for benzodiazepines and hypnotics in hair at pg/mg level by liquid chromatography-mass spectrometry/mass spectrometry.	2005-10-15	16154525
Simultaneous determination of clobazam and its major metabolite in human plasma by a rapid HPLC method.	2005-09-05	16005690
[Subacute encephalitis with anti-glutamate receptor antibodies presented with epilepsia partialis continua].	2005-08	16180713
Stiripentol.	2005-07	16022579
Screening and confirmatory method for benzodiazepines and hypnotics in oral fluid by LC-MS/MS.	2005-06-10	15944062
Neuroembryopathic effect of clobazam in rat: a histological study.	2005-06	16295712
A common variable immunodeficient patient who developed acute disseminated encephalomyelitis followed by the Lennox-Gastaut syndrome.	2005-06	15943601
Motor impairment on awakening in a patient with an EEG pattern of "unilateral, continuous spikes and waves during slow sleep".	2005-06	15929915
Evaluation of health status in epilepsy using the EQ-5D questionnaire: a prospective, observational, 6-month study of adjunctive therapy with anti-epileptic drugs.	2005-05	15969872
Visually self-induced seizures sensitive to round objects.	2005-05	15857450
Stiripentol: new preparation. Severe myoclonic epilepsy of infancy: promising.	2005-04	15875342
A case of toxic epidermal necrolysis with lesions mostly on sun-exposed skin.	2005-04	15752129
Clobazam as add-on therapy for temporal lobe epilepsy and hippocampal sclerosis.	2005-02	15825553
Effect of antiepileptic drug polytherapy on crystalluria.	2005-02	15664771
[Antiepileptic drugs in the treatment of autistic regression syndromes].	2005-01-15	15736083
Intermittent clobazam therapy in febrile seizures.	2005-01	15684445
Treatment of electrical status epilepticus during slow-wave sleep with high-dose corticosteroid.	2005-01	15607609
Management of Landau-Kleffner syndrome.	2005	16356025
Properties of antiepileptic drugs in the treatment of idiopathic generalized epilepsies.	2005	16302888
Photosensitivity in idiopathic generalized epilepsies.	2005	16302877
Levetiracetam in the treatment of infantile spasms.	2005	15701562
A major influence of CYP2C19 genotype on the steady-state concentration of N-desmethylclobazam.	2004-12	15533655
In vitro characterization of clobazam metabolism by recombinant cytochrome P450 enzymes: importance of CYP2C19.	2004-11	15483195
Affinity of various benzodiazepine site ligands in mice with a point mutation in the GABA(A) receptor gamma2 subunit.	2004-10-15	15451405
Development of a whole body physiologically based model to characterise the pharmacokinetics of benzodiazepines. 1: Estimation of rat tissue-plasma partition ratios.	2004-08	15563004
Screening, library-assisted identification and validated quantification of 23 benzodiazepines, flumazenil, zaleplone, zolpidem and zopiclone in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.	2004-08	15329838
Clobazam as a new antiepileptic drug and clorazepate dipotassium as an alternative antiepileptic drug in Japan.	2004	15610190
Therapeutic drug monitoring of old and newer anti-epileptic drugs.	2004	15576287

Patents

Sample Use Guides

In Vivo Use Guide

Patients ≤30 kg body weight: Initiate at 5 mg daily and titrate as tolerated up to 20 mg daily. Patients > 30 kg body weight: Initiate at 10 mg daily and titrate as tolerated up to 40 mg daily. For doses above 5 mg/day administer in two divided doses. Dosage adjustment needed in following groups: Geriatric patients. Known CYP2C19 poor metabolizers. Mild or moderate hepatic impairment; no information for severe hepatic impairment.

Route of Administration: Oral

In Vitro Use Guide

Recurrent ictal-like seizures (ILEs, four per hour) were generated in intact corticohippocampal formations (CHFs) of P7-8 rats, and extracellular recordings were performed in the hippocampus and neocortex. Clobazam was applied at clinically relevant concentrations (at least two), during 30 min after the third ILE. Clobazam prevented the occurrence of seizures in recurrent ictal-like seizures.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:47 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:47 GMT 2025`
Record UNII	2MRO291B4U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MYSTAN

Preferred Name

English

CLOBAZAM

Official Name

English

CLOBAZAM [MI]

Common Name

English

CLOBAZAM [JAN]

Common Name

English

URBADAN

Brand Name

English

1H-1,5-BENZODIAZEPINE-2,4(3H,5H)-DIONE, 7-CHLORO-1-METHYL-5-PHENYL-

Systematic Name

English

CLOBAZAM [ORANGE BOOK]

Common Name

English

CLOBAZAM [VANDF]

Common Name

English

FRISIUM

Brand Name

English

URBANYL

Brand Name

English

ONFI

Brand Name

English

LM 2717

Code

English

LM-2717

Code

English

COLBAZAM [VANDF]

Common Name

English

NSC-336279

Code

English

HR-376

Code

English

H 4723

Code

English

HR 376

Code

English

CLOBAZAM [EP MONOGRAPH]

Common Name

English

CLOBAZAM [MART.]

Common Name

English

7-Chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione

Common Name

English

SYMPAZAN

Brand Name

English

H-4723

Code

English

clobazam [INN]

Common Name

English

CLOBAZAM [USAN]

Common Name

English

Clobazam [WHO-DD]

Common Name

English

Classification Tree Code System Code

DEA NO.

2751