Page last updated: 2024-10-14

rwj-333369

Description

S-2-O-carbamoyl-1-o-chlorophenyl-ethanol: neuromodulator/Antiepileptic Agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6918474
CHEMBL ID2087003
CHEBI ID135966
SCHEMBL ID729003
MeSH IDM0508880

Synonyms (39)

Synonym
jnj-10234094
ykp-509
comfyde
rwj-333369
carisbamate
D06573
carisbamate (usan)
194085-75-1
CHEBI:135966
[(2s)-2-(2-chlorophenyl)-2-hydroxyethyl] carbamate
rwj 333369
s-2-o-carbamoyl-1-o-chlorophenyl-ethanol
(+)-(2s)-2-(2-chlorophenyl)-2-hydroxyethyl carbamate
unii-p7725i9v3z
carisbamate [usan:inn]
1,2-ethanediol, 1-(2-chlorophenyl)-, 2-carbamate, (1s)-
p7725i9v3z ,
1,2-ethanediol,1-(2-chlorophenyl)-, 2-carbamate, (1s)-
rwj-333369-000
CHEMBL2087003
SCHEMBL729003
(2s)-2-(2-chlorophenyl)-2-hydroxyethyl carbamate
carisbamate [who-dd]
carisbamate [mi]
carisbamate [usan]
(s)-2-o-carbamoyl-1-o-chlorophenyl-ethanol
carisbamate [inn]
(s)-2-carbamoyloxy-1-o-chlorophenylethanol
OLBWFRRUHYQABZ-MRVPVSSYSA-N
(s)-carisbamate
DTXSID70426076
DB12338
EX-A7280
rwj 333369; ykp 509
(s)-2-(2-chlorophenyl)-2-hydroxyethyl carbamate
EN300-8659675
CS-0003652
HY-14948
AKOS040751033

Toxicity

ExcerptReference
" The drug was generally safe and well tolerated."( Pharmacokinetics, safety, and tolerability of the new antiepileptic carisbamate in the elderly.
Levy, R; Novak, G; Ragueneau-Majlessi, I; Solanki, B; Yao, C; Zannikos, P, 2008
)
" Dizziness was the most common treatment-emergent adverse event, with a higher incidence (≥ 5% difference) in the combined carisbamate group (31%) than placebo (9%); the incidence was higher with carisbamate 1,200 mg (32%, n = 58) than with carisbamate 800 mg (30%, n = 53)."( A randomized, double-blind, placebo-controlled study of the efficacy, safety, and tolerability of adjunctive carisbamate treatment in patients with partial-onset seizures.
Ben-Menachem, E; Eerdekens, M; Halford, JJ; Kwan, P; Ness, S; Novak, G; Schmitt, J, 2011
)
" Dizziness was the only treatment-emergent adverse event occurring at ≥10% difference in carisbamate groups versus placebo (study 1: 12% vs."( Efficacy and safety of carisbamate in patients with diabetic neuropathy or postherpetic neuralgia: results from 3 randomized, double-blind placebo-controlled trials.
Brashear, HR; DiBernardo, A; Ford, LM; Shi, Y; Smith, T; Todd, MJ, 2014
)

Pharmacokinetics

ExcerptReference
" Plasma samples were collected for a pharmacokinetic analysis on days 1, 8, and 13."( Pharmacokinetics of carisbamate (RWJ-333369) in healthy Japanese and Western subjects.
Bialer, M; Franc, MA; Novak, G; Solanki, B; Verhaeghe, T; Yao, C; Zannikos, P, 2009
)
"Following a single dose, carisbamate Cmax and area under the curve (AUC) geometric mean ratios were 16."( Pharmacokinetics of carisbamate (RWJ-333369) in healthy Japanese and Western subjects.
Bialer, M; Franc, MA; Novak, G; Solanki, B; Verhaeghe, T; Yao, C; Zannikos, P, 2009
)
" Mean half-life (t(1/2)) values were prolonged in the moderate impairment group (21 hours) relative to the normal group (11 hours)."( Effect of mild and moderate hepatic impairment on the pharmacokinetics and safety of carisbamate.
Brashear, HR; Greenspan, A; Moore, K; Solanki, B; Verhaeghe, T; Zannikos, P, 2012
)
" Carisbamate at 600 mg (but not 200 mg) twice-daily prolonged the elimination half-life of (S)- and (R)-warfarin by ~10 hours (25% and 32% increase, respectively)."( Effect of carisbamate on the pharmacokinetics and pharmacodynamics of warfarin in healthy participants.
Ariyawansa, J; Brashear, HR; DiBernardo, A; Gonzalez, M; Zannikos, P, 2012
)

Dosage Studied

ExcerptReference
" Excretion of radioactivity was rapid and nearly complete at 96 h after dosing in all species."( Metabolism and excretion of RWJ-333369 [1,2-ethanediol, 1-(2-chlorophenyl)-, 2-carbamate, (S)-] in mice, rats, rabbits, and dogs.
Annaert, P; Bockx, M; Goris, I; Hendrickx, J; Janssen, CG; Kao, M; Kelley, MF; Mamidi, RN; Mannens, G; Meuldermans, W, 2007
)
"To characterize possible pharmacokinetic interactions between the new antiepileptic drug carisbamate (RWJ-333369) and valproic acid (VPA) or lamotrigine (LTG) following multiple dosing in healthy subjects."( An interaction study between the new antiepileptic and CNS drug carisbamate (RWJ-333369) and lamotrigine and valproic acid.
Bialer, M; Chien, S; Doose, DR; Mertens, A; Novak, G; Solanki, B; Verhaeghe, T; Yao, C, 2007
)
"This study explored the dose-response relationship of carisbamate administered at doses of 100 mg per day, 300 mg per day, or 600 mg per day, in the prevention of migraine."( Evaluation of carisbamate for the treatment of migraine in a randomized, double-blind trial.
Cady, RK; Diener, HC; Haas, M; Hu, P; Mathew, N; Novak, GP, 2009
)
" Subjects received a single oral dose of 250 mg carisbamate on day 1 followed by a 3-day washout period; twice-daily dosing of 250 mg carisbamate on days 5-8; subsequently, 500 mg on days 9-12 and a single dose of 500 mg on day 13."( Pharmacokinetics of carisbamate (RWJ-333369) in healthy Japanese and Western subjects.
Bialer, M; Franc, MA; Novak, G; Solanki, B; Verhaeghe, T; Yao, C; Zannikos, P, 2009
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID684345Anticonvulsant activity in po dosed Sprague-Dawley albino rat assessed as protection against subcutaneous metrazol-induced seizures2012Journal of medicinal chemistry, Mar-22, Volume: 55, Issue:6
Syntheses and evaluation of anticonvulsant activity of novel branched alkyl carbamates.
AID684127Neurotoxicity in po dosed Sprague-Dawley albino rat assessed as minimal motor impairment by rotarod test2012Journal of medicinal chemistry, Mar-22, Volume: 55, Issue:6
Syntheses and evaluation of anticonvulsant activity of novel branched alkyl carbamates.
AID684339Anticonvulsant activity in po dosed Sprague-Dawley albino rat assessed as protection against maximal electroshock-induced seizures2012Journal of medicinal chemistry, Mar-22, Volume: 55, Issue:6
Syntheses and evaluation of anticonvulsant activity of novel branched alkyl carbamates.
AID684348Protective index, ratio of TD50 for po dosed Sprague-Dawley albino rat by rotarod test to ED50 for po dosed Sprague-Dawley albino rat by subcutaneous metrazol seizures test2012Journal of medicinal chemistry, Mar-22, Volume: 55, Issue:6
Syntheses and evaluation of anticonvulsant activity of novel branched alkyl carbamates.
AID684342Protective index, ratio of TD50 for po dosed Sprague-Dawley albino rat by rotarod test to ED50 for po dosed Sprague-Dawley albino rat by maximal electroshock seizures test2012Journal of medicinal chemistry, Mar-22, Volume: 55, Issue:6
Syntheses and evaluation of anticonvulsant activity of novel branched alkyl carbamates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (42)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's21 (50.00)29.6817
2010's19 (45.24)24.3611
2020's2 (4.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (27.27%)5.53%
Reviews6 (13.64%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (59.09%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]