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 |
|---|---|---|---|
Target ID: CHEMBL2362995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28230232 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| "Epileptic encephalopathy" of infancy and childhood: electro-clinical pictures and recent understandings. | 2010-12 |
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| Prevention or modification of epileptogenesis after brain insults: experimental approaches and translational research. | 2010-12 |
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| Progress report on new antiepileptic drugs: a summary of the Tenth Eilat Conference (EILAT X). | 2010-12 |
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| Antiepileptic drug interactions - principles and clinical implications. | 2010-09 |
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| Emerging drugs for partial onset seizures. | 2010-09 |
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| Carisbamate in essential tremor: brief report of a proof of concept study. | 2010-04-15 |
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| Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs. | 2010-04 |
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| Gateways to clinical trials. | 2010-04 |
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| Gateways to clinical trials. | 2010-03 |
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| Carisbamate as adjunctive treatment of partial onset seizures in adults in two randomized, placebo-controlled trials. | 2010-03 |
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| What is the promise of new antiepileptic drugs in status epilepticus? Focus on brivaracetam, carisbamate, lacosamide, NS-1209, and topiramate. | 2009-12 |
|
| Gateways to clinical trials. | 2009-09 |
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| Pharmacokinetics of carisbamate (RWJ-333369) in healthy Japanese and Western subjects. | 2009-08 |
|
| Carisbamate, a novel antiepileptic candidate compound, attenuates alcohol intake in alcohol-preferring rats. | 2009-08 |
|
| Investigation of the effects of the novel anticonvulsant compound carisbamate (RWJ-333369) on rat piriform cortical neurones in vitro. | 2009-03 |
|
| Evaluation of carisbamate for the treatment of migraine in a randomized, double-blind trial. | 2009-02 |
|
| Carisbamate, a novel neuromodulator, inhibits voltage-gated sodium channels and action potential firing of rat hippocampal neurons. | 2009-01 |
|
| Progress report on new antiepileptic drugs: a summary of the Ninth Eilat Conference (EILAT IX). | 2009-01 |
|
| Pregabalin for the management of partial epilepsy. | 2008-12 |
|
| Randomized, controlled, dose-ranging trial of carisbamate for partial-onset seizures. | 2008-11-11 |
|
| One-pot conversion of trimethylsilyl ethers into urethanes using chlorosulfonyl isocyanate: application to the synthesis of a novel neuromodulator carisbamate. | 2008-11 |
|
| A new potential AED, carisbamate, substantially reduces spontaneous motor seizures in rats with kainate-induced epilepsy. | 2008-10 |
|
| Carisbamate prevents the development and expression of spontaneous recurrent epileptiform discharges and is neuroprotective in cultured hippocampal neurons. | 2008-10 |
|
| The novel antiepileptic drug carisbamate (RWJ 333369) is effective in inhibiting spontaneous recurrent seizure discharges and blocking sustained repetitive firing in cultured hippocampal neurons. | 2008-05 |
|
| Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions. | 2008-03-02 |
|
| Gateways to clinical trials. | 2008-03 |
|
| Pharmacokinetics, safety, and tolerability of the new antiepileptic carisbamate in the elderly. | 2008-03 |
|
| Effects of carisbamate (RWJ-333369) in two models of genetically determined generalized epilepsy, the GAERS and the audiogenic Wistar AS. | 2008-03 |
|
| Modifications of antiepileptic drugs for improved tolerability and efficacy. | 2008-02-14 |
|
| Pharmacotherapy of essential tremor : an overview of existing and upcoming agents. | 2008 |
|
| Pharmacological management of epilepsy: recent advances and future prospects. | 2008 |
|
| Carisbamate, a new carbamate for the treatment of epilepsy. | 2007-10 |
|
| Gateways to clinical trials. | 2007-09 |
|
| An interaction study between the new antiepileptic and CNS drug carisbamate (RWJ-333369) and lamotrigine and valproic acid. | 2007-07 |
|
| Evaluation of carisbamate, a novel antiepileptic drug, in photosensitive patients: an exploratory, placebo-controlled study. | 2007-05 |
|
| Carisbamate (RWJ-333369). | 2007-01 |
| Substance Class |
Chemical
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