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
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
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2362995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28230232 |
PubMed
Title | Date | PubMed |
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Carisbamate (RWJ-333369). | 2007 Jan |
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An interaction study between the new antiepileptic and CNS drug carisbamate (RWJ-333369) and lamotrigine and valproic acid. | 2007 Jul |
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Evaluation of carisbamate, a novel antiepileptic drug, in photosensitive patients: an exploratory, placebo-controlled study. | 2007 May |
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Carisbamate, a new carbamate for the treatment of epilepsy. | 2007 Oct |
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Gateways to clinical trials. | 2007 Sep |
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Pharmacotherapy of essential tremor : an overview of existing and upcoming agents. | 2008 |
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Pharmacological management of epilepsy: recent advances and future prospects. | 2008 |
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Pregabalin for the management of partial epilepsy. | 2008 Dec |
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Modifications of antiepileptic drugs for improved tolerability and efficacy. | 2008 Feb 14 |
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Gateways to clinical trials. | 2008 Mar |
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Pharmacokinetics, safety, and tolerability of the new antiepileptic carisbamate in the elderly. | 2008 Mar |
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Effects of carisbamate (RWJ-333369) in two models of genetically determined generalized epilepsy, the GAERS and the audiogenic Wistar AS. | 2008 Mar |
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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 |
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One-pot conversion of trimethylsilyl ethers into urethanes using chlorosulfonyl isocyanate: application to the synthesis of a novel neuromodulator carisbamate. | 2008 Nov |
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Randomized, controlled, dose-ranging trial of carisbamate for partial-onset seizures. | 2008 Nov 11 |
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A new potential AED, carisbamate, substantially reduces spontaneous motor seizures in rats with kainate-induced epilepsy. | 2008 Oct |
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Carisbamate prevents the development and expression of spontaneous recurrent epileptiform discharges and is neuroprotective in cultured hippocampal neurons. | 2008 Oct |
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Pharmacokinetics of carisbamate (RWJ-333369) in healthy Japanese and Western subjects. | 2009 Aug |
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Carisbamate, a novel antiepileptic candidate compound, attenuates alcohol intake in alcohol-preferring rats. | 2009 Aug |
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What is the promise of new antiepileptic drugs in status epilepticus? Focus on brivaracetam, carisbamate, lacosamide, NS-1209, and topiramate. | 2009 Dec |
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Evaluation of carisbamate for the treatment of migraine in a randomized, double-blind trial. | 2009 Feb |
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Carisbamate, a novel neuromodulator, inhibits voltage-gated sodium channels and action potential firing of rat hippocampal neurons. | 2009 Jan |
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Progress report on new antiepileptic drugs: a summary of the Ninth Eilat Conference (EILAT IX). | 2009 Jan |
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Investigation of the effects of the novel anticonvulsant compound carisbamate (RWJ-333369) on rat piriform cortical neurones in vitro. | 2009 Mar |
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Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions. | 2009 Mar-Apr |
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Gateways to clinical trials. | 2009 Sep |
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Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs. | 2010 Apr |
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Gateways to clinical trials. | 2010 Apr |
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Carisbamate in essential tremor: brief report of a proof of concept study. | 2010 Apr 15 |
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"Epileptic encephalopathy" of infancy and childhood: electro-clinical pictures and recent understandings. | 2010 Dec |
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Prevention or modification of epileptogenesis after brain insults: experimental approaches and translational research. | 2010 Dec |
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Progress report on new antiepileptic drugs: a summary of the Tenth Eilat Conference (EILAT X). | 2010 Dec |
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Gateways to clinical trials. | 2010 Mar |
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Carisbamate as adjunctive treatment of partial onset seizures in adults in two randomized, placebo-controlled trials. | 2010 Mar |
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Antiepileptic drug interactions - principles and clinical implications. | 2010 Sep |
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Emerging drugs for partial onset seizures. | 2010 Sep |
Substance Class |
Chemical
Created
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P7725I9V3Z
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362511
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594117
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CARISBAMATE
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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