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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H10ClNO3
Molecular Weight 215.634
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARISBAMATE

SMILES

NC(=O)OC[C@@H](O)C1=CC=CC=C1Cl

InChI

InChIKey=OLBWFRRUHYQABZ-MRVPVSSYSA-N
InChI=1S/C9H10ClNO3/c10-7-4-2-1-3-6(7)8(12)5-14-9(11)13/h1-4,8,12H,5H2,(H2,11,13)/t8-/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H10ClNO3
Molecular Weight 215.634
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Carisbamate is an experimental anticonvulsant drug that was under development by Johnson & Johnson Pharmaceutical Research and Development but never marketed. Acute and chronic nonclinical toxicological studies have not revealed any significant abnormalities other than dose-related CNS toxicity. Carisbamate displays high potency in a broad range of rodent seizure and epilepsy models at doses well below those that produce CNS toxicity. The exact mechanism of action is unknown but neuroprotective and antiseizure activity of Carisbamate likely results in part from decreased calcium accumulation through blockade of T-type Ca2+ channels. A phase II clinical trial in the treatment of partial seizures demonstrated that the compound has efficacy in the treatment of partial seizures and a good safety profile. In large multicenter phase III clinical trial for the treatment of partial seizures carisbamate at doses of 300, 800, and 1,600 mg/d was effective as adjunctive therapy for reducing the frequency of partial-onset seizures. The most common adverse events, encountered mainly at daily doses of 1000 mg or more, were CNS-related, including headache, dizziness, somnolence, and nausea. In another phase III clinical trial, carisbamate was not more efficacious in migraine prophylaxis than placebo, but carisbamate monotherapy was well tolerated at doses up to 600 mg per day. Johnson & Johnson received provisional approval by the FDA to market carisbamate under the brand name of Comfyde. However, on August 21, 2009, Johnson & Johnson reported that the FDA had failed to give marketing approval.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Carisbamate (RWJ-333369).
2007 Jan
An interaction study between the new antiepileptic and CNS drug carisbamate (RWJ-333369) and lamotrigine and valproic acid.
2007 Jul
Evaluation of carisbamate, a novel antiepileptic drug, in photosensitive patients: an exploratory, placebo-controlled study.
2007 May
Carisbamate, a new carbamate for the treatment of epilepsy.
2007 Oct
Gateways to clinical trials.
2007 Sep
Pharmacotherapy of essential tremor : an overview of existing and upcoming agents.
2008
Pharmacological management of epilepsy: recent advances and future prospects.
2008
Pregabalin for the management of partial epilepsy.
2008 Dec
Modifications of antiepileptic drugs for improved tolerability and efficacy.
2008 Feb 14
Gateways to clinical trials.
2008 Mar
Pharmacokinetics, safety, and tolerability of the new antiepileptic carisbamate in the elderly.
2008 Mar
Effects of carisbamate (RWJ-333369) in two models of genetically determined generalized epilepsy, the GAERS and the audiogenic Wistar AS.
2008 Mar
The novel antiepileptic drug carisbamate (RWJ 333369) is effective in inhibiting spontaneous recurrent seizure discharges and blocking sustained repetitive firing in cultured hippocampal neurons.
2008 May
One-pot conversion of trimethylsilyl ethers into urethanes using chlorosulfonyl isocyanate: application to the synthesis of a novel neuromodulator carisbamate.
2008 Nov
Randomized, controlled, dose-ranging trial of carisbamate for partial-onset seizures.
2008 Nov 11
A new potential AED, carisbamate, substantially reduces spontaneous motor seizures in rats with kainate-induced epilepsy.
2008 Oct
Carisbamate prevents the development and expression of spontaneous recurrent epileptiform discharges and is neuroprotective in cultured hippocampal neurons.
2008 Oct
Pharmacokinetics of carisbamate (RWJ-333369) in healthy Japanese and Western subjects.
2009 Aug
Carisbamate, a novel antiepileptic candidate compound, attenuates alcohol intake in alcohol-preferring rats.
2009 Aug
What is the promise of new antiepileptic drugs in status epilepticus? Focus on brivaracetam, carisbamate, lacosamide, NS-1209, and topiramate.
2009 Dec
Evaluation of carisbamate for the treatment of migraine in a randomized, double-blind trial.
2009 Feb
Carisbamate, a novel neuromodulator, inhibits voltage-gated sodium channels and action potential firing of rat hippocampal neurons.
2009 Jan
Progress report on new antiepileptic drugs: a summary of the Ninth Eilat Conference (EILAT IX).
2009 Jan
Investigation of the effects of the novel anticonvulsant compound carisbamate (RWJ-333369) on rat piriform cortical neurones in vitro.
2009 Mar
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.
2009 Mar-Apr
Gateways to clinical trials.
2009 Sep
Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs.
2010 Apr
Gateways to clinical trials.
2010 Apr
Carisbamate in essential tremor: brief report of a proof of concept study.
2010 Apr 15
"Epileptic encephalopathy" of infancy and childhood: electro-clinical pictures and recent understandings.
2010 Dec
Prevention or modification of epileptogenesis after brain insults: experimental approaches and translational research.
2010 Dec
Progress report on new antiepileptic drugs: a summary of the Tenth Eilat Conference (EILAT X).
2010 Dec
Gateways to clinical trials.
2010 Mar
Carisbamate as adjunctive treatment of partial onset seizures in adults in two randomized, placebo-controlled trials.
2010 Mar
Antiepileptic drug interactions - principles and clinical implications.
2010 Sep
Emerging drugs for partial onset seizures.
2010 Sep
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:25:00 GMT 2023
Edited
by admin
on Sat Dec 16 17:25:00 GMT 2023
Record UNII
P7725I9V3Z
Record Status Validated (UNII)
Record Version
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Name Type Language
CARISBAMATE
DASH   INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
YKP-509
Code English
CARISBAMATE [USAN]
Common Name English
(S)-2-O-CARBAMOYL-1-O-CHLOROPHENYL-ETHANOL
Common Name English
CARISBAMATE [MI]
Common Name English
carisbamate [INN]
Common Name English
JNJ-10234094
Code English
RWJ-333369-000
Code English
Carisbamate [WHO-DD]
Common Name English
(+)-(2S)-2-(2-CHLOROPHENYL)-2-HYDROXYETHYL CARBAMATE
Systematic Name English
1,2-ETHANEDIOL, 1-(2-CHLOROPHENYL)-, 2-CARBAMATE, (1S)-
Common Name English
RWJ-333369
Code English
(2S)-2-(2-Chlorophenyl)-2-hydroxyethyl carbamate
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
WHO-VATC QN03AX19
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
WHO-ATC N03AX19
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
FDA ORPHAN DRUG 362511
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
FDA ORPHAN DRUG 594117
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
Code System Code Type Description
FDA UNII
P7725I9V3Z
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
DRUG CENTRAL
4400
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
INN
8816
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
CAS
194085-75-1
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
SMS_ID
100000156560
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
DRUG BANK
DB12338
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
EVMPD
SUB130483
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID70426076
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
USAN
RR-75
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
MESH
C518914
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
MERCK INDEX
m3111
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY Merck Index
PUBCHEM
6918474
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
ChEMBL
CHEMBL2087003
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
WIKIPEDIA
CARISBAMATE
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
NCI_THESAURUS
C75161
Created by admin on Sat Dec 16 17:25:02 GMT 2023 , Edited by admin on Sat Dec 16 17:25:02 GMT 2023
PRIMARY
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EXCRETED UNCHANGED
URINE
EXCRETED UNCHANGED
TRACE AMOUNT
FECAL
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Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE

Tmax PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE