Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H13ClN2O2 |
Molecular Weight | 300.7402 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1c2ccc(cc2N(c3ccccc3)C(=O)CC1=O)Cl
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
Molecular Formula | C16H13ClN2O2 |
Molecular Weight | 300.7402 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator'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
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.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/35198
Curator's Comment:: Discovery of Clobazam at the Maestretti Research Laboratories was first published in 1969. Maestretti Research Laboratories became part of Sanofi.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22145708 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | ONFI Approved UseIndicated for the adjunctive treatment of seizures associated with Lennox-Gastaut syndrome (LGS) in patients 2 years of age or older. Launch Date1.31915514E12 |
Cmax
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
36 h |
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Disc. AE: Somnolence, Depressed mood... Other AEs: Delirium... AEs leading to discontinuation/dose reduction: Somnolence (1 patient) Other AEs: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) Delirium (2 patients) Sources: Page: p. 69-70 |
10 mg 2 times / day steady, oral Dose: 10 mg, 2 times / day Route: oral Route: steady Dose: 10 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Disc. AE: Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Sources: Page: p. 69 |
15 mg 2 times / day steady, oral Dose: 15 mg, 2 times / day Route: oral Route: steady Dose: 15 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Disc. AE: Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Sources: Page: p. 69 |
20 mg 2 times / day steady, oral Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Sources: Page: p. 70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 70 |
Disc. AE: Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (2 patients) Sources: Page: p. 70 |
60 mg 2 times / day steady, oral Dose: 60 mg, 2 times / day Route: oral Route: steady Dose: 60 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Disc. AE: Somnolence... AEs leading to discontinuation/dose reduction: Somnolence (1 patient) Sources: Page: p. 69 |
70 mg 2 times / day steady, oral Dose: 70 mg, 2 times / day Route: oral Route: steady Dose: 70 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Disc. AE: Dizziness, Somnolence... AEs leading to discontinuation/dose reduction: Dizziness (1 patient) Sources: Page: p. 69Somnolence (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Depressed mood | 1 patient Disc. AE |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Dizziness | 1 patient Disc. AE |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Dysarthria | 1 patient Disc. AE |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Erectile dysfunction | 1 patient Disc. AE |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Insomnia | 1 patient Disc. AE |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Libido decreased | 1 patient Disc. AE |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Somnolence | 1 patient Disc. AE |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Unsteady gait | 1 patient Disc. AE |
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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Delirium | 2 patients | 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: Page: p. 69-70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 69-70 |
Transaminases increased | 1 patient Disc. AE |
10 mg 2 times / day steady, oral Dose: 10 mg, 2 times / day Route: oral Route: steady Dose: 10 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Transaminases increased | 1 patient Disc. AE |
15 mg 2 times / day steady, oral Dose: 15 mg, 2 times / day Route: oral Route: steady Dose: 15 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Transaminases increased | 2 patients Disc. AE |
20 mg 2 times / day steady, oral Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Sources: Page: p. 70 |
healthy n = 70 Health Status: healthy Population Size: 70 Sources: Page: p. 70 |
Somnolence | 1 patient Disc. AE |
60 mg 2 times / day steady, oral Dose: 60 mg, 2 times / day Route: oral Route: steady Dose: 60 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Dizziness | 1 patient Disc. AE |
70 mg 2 times / day steady, oral Dose: 70 mg, 2 times / day Route: oral Route: steady Dose: 70 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Somnolence | 1 patient Disc. AE |
70 mg 2 times / day steady, oral Dose: 70 mg, 2 times / day Route: oral Route: steady Dose: 70 mg, 2 times / day Sources: Page: p. 69 |
healthy n = 24 Health Status: healthy Population Size: 24 Sources: Page: p. 69 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 16.0 |
no | |||
Page: 16.0 |
no | |||
Page: 16.0 |
no | |||
Page: 16.0 |
no | |||
Page: 16.0 |
no | |||
Page: 17.0 |
no | |||
Page: 16.0 |
no | |||
Page: 16.0 |
no | |||
Page: 16.0 |
no | |||
Page: 16.0 |
no | |||
Page: 16.0 |
no | yes (co-administration study) Comment: clobazam increased dextromethorphan cmax 90%, auc 59% Page: 16.0 |
||
Page: 17.0 |
weak | |||
Page: 9.0 |
weak | yes (co-administration study) Comment: clobazam decreased midazolam auc 27%, cmax 24% Page: 9.0 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 15.0 |
major | yes (co-administration study) Comment: ketoconazole increased clobazam auc 54%, no effect on cmax Page: 15.0 |
||
Page: 15.0 |
minor | |||
Page: 15.0 |
minor | yes (co-administration study) Comment: omeprazole increased clobazam auc 30-36%, no effect on cmax Page: 15.0 |
||
Page: 96.0 |
no | |||
Page: 17.0 |
yes | yes (co-administration study) Comment: verapamil reduced clobazam transport >96% Page: 17.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 20.0 |
PubMed
Title | Date | PubMed |
---|---|---|
[Psychomotor slowness of a mentally retarded woman]. | 2001 |
|
Management strategies for refractory localization-related seizures. | 2001 |
|
Epileptic encephalopathy. | 2001 |
|
[A pharmacological profile of clobazam (Mystan), a new antiepileptic drug]. | 2001 Aug |
|
[Rolandic discharges in childhood epilepsy: magnetoencephalographic diagnosis]. | 2001 Aug 16-31 |
|
Induction of hypersensitivity to a previously tolerated antiepileptic drug by a second antiepileptic drug. | 2001 Mar |
|
[Epileptic crisis after antimalaria chemoprophylaxis with chloroquine]. | 2001 Nov 24 |
|
Infantile spasms: diagnosis and assessment of treatment response by video-EEG. | 2001 Oct |
|
Atypical evolution in childhood epilepsy with occipital paroxysms (Panayiotopoulos type). | 2001 Sep |
|
Psychosomatic reactions to a stressful environment and an attempt at pharmacological modification. | 2001 Sep-Oct |
|
Long-term neuropsychological follow-up and nosological considerations in five patients with continuous spikes and waves during slow sleep. | 2002 Dec |
|
Treatment of trigeminal neuralgia: letter to editor. | 2002 Jun |
|
Anti-epileptic drugs. | 2002 May |
|
Clobazam shows a different antiepileptic action profile from clonazepam and zonisamide in Ihara epileptic rats. | 2002 May |
|
[Long-term efficacy and tolerance of stiripentaol in severe myoclonic epilepsy of infancy (Dravet's syndrome)]. | 2002 Nov |
|
Vagus nerve stimulation in a case of epilepsy with CSWSS: respiratory side effects during sleep. | 2002 Oct |
|
A casuistic rationale for the treatment of spastic and myocloni in a childhood neurodegenerative disease: neuronal ceroid lipofuscinosis of the type Jansky-Bielschowsky. | 2002 Oct-Dec |
|
A case of nonconvulsive status epilepticus associated with focal cortical dysplasia. | 2003 Apr |
|
Phenytoin toxicity due to fluoropyrimidines (5FU/capecitabine): three case reports. | 2003 Aug 18 |
|
Mechanism of clobazam-induced thyroidal oncogenesis in male rats. | 2003 Dec 10 |
|
Use of clobazam for the treatment of refractory complex partial seizures. | 2003 Jul |
|
Clobazam monotherapy in drug naïve adult patients with epilepsy. | 2003 Jun |
|
[A case of intractable epilepsy showing frequent gelastic seizures by administration of clobazam]. | 2003 Sep |
|
Clobazam as a new antiepileptic drug and clorazepate dipotassium as an alternative antiepileptic drug in Japan. | 2004 |
|
Hypersensitivity to topiramate sprinkle capsules does not preclude the use of topiramate tablets. | 2004 |
|
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 Aug |
|
A major influence of CYP2C19 genotype on the steady-state concentration of N-desmethylclobazam. | 2004 Dec |
|
Unusual side-effects due to clobazam: a case report with genetic study of CYP2C19. | 2004 Jan |
|
Miconazole and clobazam; a useful interaction in Dravet's syndrome? | 2004 Jan |
|
[Idiopathic epilepsies: some therapeutic aspects]. | 2004 Jan 16-31 |
|
Sporadic major hyperekplexia in neonates and infants: clinical manifestations and outcome. | 2004 Jul |
|
Forensic intoxication with clobazam: HPLC/DAD/MSD analysis. | 2004 Jul 16 |
|
In vitro characterization of clobazam metabolism by recombinant cytochrome P450 enzymes: importance of CYP2C19. | 2004 Nov |
|
Affinity of various benzodiazepine site ligands in mice with a point mutation in the GABA(A) receptor gamma2 subunit. | 2004 Oct 15 |
|
The difficulty in diagnosing non-convulsive status epilepticus during routine medical practice. | 2004 Sep |
|
Photosensitivity in idiopathic generalized epilepsies. | 2005 |
|
Levetiracetam in the treatment of infantile spasms. | 2005 |
|
A case of toxic epidermal necrolysis with lesions mostly on sun-exposed skin. | 2005 Apr |
|
[Subacute encephalitis with anti-glutamate receptor antibodies presented with epilepsia partialis continua]. | 2005 Aug |
|
Intermittent clobazam therapy in febrile seizures. | 2005 Jan |
|
[Antiepileptic drugs in the treatment of autistic regression syndromes]. | 2005 Jan 15 |
|
Neuroembryopathic effect of clobazam in rat: a histological study. | 2005 Jun |
|
A common variable immunodeficient patient who developed acute disseminated encephalomyelitis followed by the Lennox-Gastaut syndrome. | 2005 Jun |
|
Levetiracetam in idiopathic generalised epilepsy and porphyria cutanea tarda. | 2006 |
|
[Epilepsy: which therapy in acute care?]. | 2006 Dec 8 |
|
Benign angiopathy of the central nervous system associated with phenytoin intoxication. | 2006 Jun |
|
Treatment in the pediatric emergency department is evidence based: a retrospective analysis. | 2006 Oct 6 |
|
Effectiveness of clobazam as add-on therapy in children with refractory focal epilepsy. | 2006 Sep |
|
Clobazam. | 2007 Jan |
|
Stiripentol. | 2007 Jan |
Sample Use Guides
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/14636342
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
Edited
Fri Jun 25 21:15:48 UTC 2021
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on
Fri Jun 25 21:15:48 UTC 2021
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Record UNII |
2MRO291B4U
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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DEA NO. |
2751
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FDA ORPHAN DRUG |
248307
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LIVERTOX |
218
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WHO-ATC |
N05BA09
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NCI_THESAURUS |
C28197
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WHO-VATC |
QN05BA09
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NDF-RT |
N0000175694
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Code System | Code | Type | Description | ||
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22316-47-8
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CLOBAZAM
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C012255
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22316-47-8
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2789
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3055
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DB00349
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SUB06673MIG
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CHEMBL70418
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8343
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2MRO291B4U
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C81615
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244-908-7
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Clobazam
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21241
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M3626
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N0000182137
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PRIMARY | Cytochrome P450 2D6 Inhibitors [MoA] | ||
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7149
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682
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METABOLIC ENZYME -> INDUCER | |||
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
FECAL
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EXCRETED UNCHANGED |
Clobazam is cleared mainly by metabolism with subsequent renal elimination of metabolites. In a mass balance study, 82% of the dose administered was recovered in the urine and 11% in the feces. Clobazam represents ~2 % of the dose recovered in urine.
URINE
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MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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