U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H10ClN3O3
Molecular Weight 315.711
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLONAZEPAM

SMILES

[O-][N+](=O)C1=CC=C2NC(=O)CN=C(C3=CC=CC=C3Cl)C2=C1

InChI

InChIKey=DGBIGWXXNGSACT-UHFFFAOYSA-N
InChI=1S/C15H10ClN3O3/c16-12-4-2-1-3-10(12)15-11-7-9(19(21)22)5-6-13(11)18-14(20)8-17-15/h1-7H,8H2,(H,18,20)

HIDE SMILES / InChI

Description

Clonazepam, a benzodiazepine, is used primarily as an anticonvulsant in the treatment of absence seizures, petit mal variant seizures (Lennox-Gastaut syndrome), akinetic and myoclonic seizures, and nocturnal myoclonus. Klonopin is the brand name for Clonazepam, an anxiolytic and anticonvulsant. The precise mechanism by which clonazepam exerts its antiseizure and antipanic effects is unknown, although it is believed to be related to its ability to enhance the activity of gamma aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. Allosteric interactions between central benzodiazepine receptors and gamma-aminobutyric acid (GABA) receptors potentiate the effects of GABA. As GABA is an inhibitory neurotransmitter, this results in increased inhibition of the ascending reticular activating system. Benzodiazepines, in this way, block the cortical and limbic arousal that occurs following stimulation of the reticular pathways.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Cerebellar Ataxia.
2000 May
Pharmacological options for the treatment of Tourette's disorder.
2001
[Clonazepam in the treatment of labile arterial hypertension in the elderly].
2001
Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis.
2001
Asymptomatic QTc prolongation associated with quetiapine fumarate overdose in a patient being treated with risperidone.
2001 Apr
Restless legs syndrome (RLS) and periodic limb movement disorder (PLMD): acute placebo-controlled sleep laboratory studies with clonazepam.
2001 Apr
Expression of the peripheral-type benzodiazepine receptor and apoptosis induction in hepatic stellate cells.
2001 Apr
Gamma irradiation effects on stability of poly(lactide-co-glycolide) microspheres containing clonazepam.
2001 Aug 10
Pharmacoepidemiologic investigation of a clonazepam-carbamazepine interaction by mixed effect modeling using routine clinical pharmacokinetic data in Japanese patients.
2001 Dec
Roles for mitochondrial and reverse mode Na+/Ca2+ exchange and the plasmalemma Ca2+ ATPase in post-tetanic potentiation at crayfish neuromuscular junctions.
2001 Dec 15
Determination of the antiepileptics vigabatrin and gabapentin in dosage forms and biological fluids using Hantzsch reaction.
2001 Feb
Results of intensive chemotherapy followed by hematopoietic stem-cell rescue in 22 patients with refractory or recurrent primary CNS lymphoma or intraocular lymphoma.
2001 Feb 1
Evaluation of native GABA(A) receptors containing an alpha 5 subunit.
2001 Feb 9
Acute effect of different antidepressants on glycemia in diabetic and non-diabetic rats.
2001 Jan
Benign segmental myoclonus: electrophysiological evidence of transient dysfunction in the brainstem.
2001 Jan
Effects of antiepileptic drugs on rat platelet aggregation: ex vivo and in vitro study.
2001 Jan
Early coadministration of clonazepam with sertraline for panic disorder.
2001 Jul
Antiepileptic drug utilization: a Danish prescription database analysis.
2001 Jul
A 28-year-old woman with panic disorder.
2001 Jul 25
Acquired pendular nystagmus with voluntary inhibition.
2001 Jun
Melatonin therapy for REM sleep behavior disorder.
2001 Jun
Peripheral-type benzodiazepine receptor ligands: mitochondrial permeability transition induction in rat cardiac tissue.
2001 Mar 15
Interaction of GYKI 52466, a selective non-competitive antagonist of AMPA/kainate receptors, with conventional antiepileptic drugs in amygdala-kindled seizures in rats.
2001 Mar-Apr
Selective, high-resolution fluorescence imaging of mitochondrial Ca2+ concentration.
2001 Nov
Determination of benzodiazepines in human hair by on-line high-performance liquid chromatography using a restricted access extraction column.
2001 Nov 15
Diazepam inhibits HIV-1 Tat-induced migration of human microglia.
2001 Oct
2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands.
2001 Oct
Effect of clonazepam treatment on antipsychotic drug-induced Meige syndrome and changes in plasma levels of GABA, HVA, and MHPG during treatment.
2001 Oct
Nutritional parameters modify muricidal behavior of male Wistar rats: preventive effects of amino acids and 4' Cl diazepam.
2001 Oct 26
Evaluation of in vitro percutaneous absorption of lorazepam and clonazepam from hydro-alcoholic gel formulations.
2001 Oct 9
[Efficacy of anticonvulsants on acute encephalitis with refractory, repetitive partial seizures (AERRPS)].
2001 Sep
Topiramate as a mood stabilizer.
2001 Sep
Hyperekplexia in neonates.
2001 Sep
Evaluation of polymeric nanoparticles composed of cholic acid and methoxy poly(ethylene glycol).
2001 Sep 11
Myoclonus during prolonged treatment with sertraline in an adolescent patient.
2001 Summer
Patents

Sample Use Guides

In Vivo Use Guide
Seizure Disorders: Adults: The initial dose for adults with seizure disorders should not exceed 1.5 mg/day divided into three doses. Dosage may be increased in increments of 0.5 to 1 mg every 3 days until seizures are adequately controlled or until side effects preclude any further increase. Maintenance dosage must be individualized for each patient depending upon response. Maximum recommended daily dose is 20 mg. Clonazepam is available as a tablet or an orally disintegrating tablet (wafer). The tablets should be administered with water by swallowing the tablet whole. The orally disintegrating tablet should be administered as follows: After opening the pouch, peel back the foil on the blister. Do not push tablet through foil. Immediately upon opening the blister, using dry hands, remove the tablet and place it in the mouth. Tablet disintegration occurs rapidly in saliva so it can be easily swallowed with or without water.
Route of Administration: Oral
In Vitro Use Guide
Clonazepam (100 nM) increased inhibitory postsynaptic current (IPSC) decay time constants in rat thalamic nuclei-the reticular nucleus (nRt) (from 44.3 to 77.9 ms, P < 0.01) but not in the ventrobasal (VB) complex..
Name Type Language
CLONAZEPAM
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
NSC-179913
Code English
CLONAZEPAM [JAN]
Common Name English
RIVOTRIL
Brand Name English
RO-5-4023
Code English
CLONAZEPAM [MART.]
Common Name English
RIVATRIL
Brand Name English
RO 5-4023
Code English
2H-1,4-BENZODIAZEPIN-2-ONE, 5-(2-CHLOROPHENYL)-1,3-DIHYDRO-7-NITRO-
Systematic Name English
CLONAZEPAM [ORANGE BOOK]
Common Name English
5-(O-CHLOROPHENYL)-1,3-DIHYDRO-7-NITRO-2H-1,4-BENZODIAZEPIN-2-ONE
Common Name English
CLONAZEPAM [MI]
Common Name English
KLONOPIN
Brand Name English
CLONAZEPAM [EP]
Common Name English
RO-54023
Code English
CLONAZEPAM [WHO-DD]
Common Name English
CLONAZEPAM [INN]
Common Name English
RAVOTRIL
Brand Name English
CLONAZEPAM [VANDF]
Common Name English
CLONAZEPAM [USP]
Common Name English
CLONAZEPAM CIV [USP-RS]
Common Name English
CLONAZEPAM [HSDB]
Common Name English
CLONAZEPAM CIV
USP-RS  
Common Name English
CLONAZEPAM [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175694
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
WHO-VATC QN03AE01
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
NCI_THESAURUS C264
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
FDA ORPHAN DRUG 243507
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
WHO-ATC N03AE01
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
NDF-RT N0000007542
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
NCI_THESAURUS C1012
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
DEA NO. 2737
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
LIVERTOX 224
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
FDA ORPHAN DRUG 82794
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
Code System Code Type Description
PUBCHEM
2802
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
WIKIPEDIA
CLONAZEPAM
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
RXCUI
2598
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB01068
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
CAS
1622-61-3
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
MESH
D002998
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
MERCK INDEX
M3649
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY Merck Index
LactMed
1622-61-3
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
ECHA (EC/EINECS)
216-596-2
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
EPA CompTox
1622-61-3
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
INN
2765
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
NCI_THESAURUS
C28935
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
EVMPD
SUB06728MIG
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
ChEMBL
CHEMBL452
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
HSDB
1622-61-3
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY
IUPHAR
6963
Created by admin on Tue Oct 22 00:34:51 UTC 2019 , Edited by admin on Tue Oct 22 00:34:51 UTC 2019
PRIMARY