ChemicalBook Product Catalog API Nervous system drugs Antiepileptic and anticonvulsant 2-(2-Chlorophenyl)-2-hydroxyethyl carbamate

2-(2-Chlorophenyl)-2-hydroxyethyl carbamate

Product Name2-(2-Chlorophenyl)-2-hydroxyethyl carbamate
CAS194085-75-1
MFC813CH8D2Cl15NO3
MW215.63
EINECS
MOL File194085-75-1.mol

Chemical Properties

Melting point	131-132°C
storage temp.	Refrigerator
solubility	DMSO (Slightly), Methanol (Slightly)
form	Solid
color	White to Off-White
optical activity	[α]/D +77 to +87°, c =0.2 in chloroform-d
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
InChIKey	OLBWFRRUHYQABZ-MRVPVSSYSA-N
SMILES	ClC1=C([C@H](O)COC(N)=O)C=CC=C1

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Carisbamate is an antiepileptic agent., In vivo, administration of carisbamate (10-60 mg/kg) dose-dependently reduces spike and wave discharges in the frontoparietal cortex in a rat model of absence seizures. Carisbamate (10 mg/kg) increases latency to the first running episode in the Wistar audiogenic sensitive rat model of convulsive seizures. It also reduces motor seizure frequency in a rat model of spontaneous seizures in a dose-dependent manner. Carisbamate blocks Na_v1.2 channels (IC₅₀ = 68 μM for rat channels) and inhibits repetitive firing of action potentials in rat hippocampal neurons in a dose-dependent manner. It also reduces T-type Ca²⁺ currents in HEK cells transfected with human recombinant Ca_v3.1 channels at a concentration of 300 μM.

Uses

Labelled Carisbamate; it is being developed for adjuvant treatment of partial onset epilepsy. Carisbamate produces anticonvulsant effects in primary generalized, complex partial and absence-type seizu re models, and exhibits neuroprotective and antiepileptogenic properties in rodent epilepsy models.

Uses

Carisbamate is being developed for adjuvant treatment of partial onset epilepsy. Carisbamate produces anticonvulsant effects in primary generalized, complex partial and absence-type seizure models, and exhibits neuroprotective and antiepileptogenic properties in rodent epilepsy models.

Definition

ChEBI: Carisbamate is an organochlorine compound.

in vivo

Carisbamate (10, 30, 60 mg/kg; i.p.; single) dose dependently reduces the expression of spike-and-wave discharges (SWD) in absence seizures rat model^[2].
Carisbamate (20, 30 mg/kg; i.p.; single) shows no wild running episode or tonic seizure occurres in any of the rats tested^[2].

Animal Model:	Male genetic absence epilepsy rat (absence seizures model)^[2].
Dosage:	10, 30, 60 mg/kg
Administration:	Intraperitoneal injection; single.
Result:	Completely inhibited SWD when at 60 mg/kg after 120 min, and restored the duration of SWD to the control level when at 30 mg/kg after 100 min.

Animal Model:	Male Wistar audiogenic sensitive rat (convulsive seizures model)^[2].
Dosage:	10, 20, 30 mg/kg
Administration:	Intraperitoneal injection; single.
Result:	Showed no wild running episode or tonic seizure occurred in any of the rats tested when at 20 and 30 mg/kg. Increased by 327% the latency to the tonic seizure that still occurred in the six of eight rats studied when at 10 mg/kg.

References

[1] JENNIFER FRANOIS Astrid N Any Boehrer. Effects of Carisbamate (RWJ-333369) in Two Models of Genetically Determined Generalized Epilepsy, the GAERS and the Audiogenic Wistar AS[J]. Epilepsia, 2007, 49 3: 393-399. DOI: 10.1111/j.1528-1167.2007.01278.x
[2] HEIDI L. GRABENSTATTER F. E D. A new potential AED, carisbamate, substantially reduces spontaneous motor seizures in rats with kainate-induced epilepsy[J]. Epilepsia, 2008, 49 10: 1787-1794. DOI: 10.1111/j.1528-1167.2008.01657.x
[3] YI LIU . Carisbamate, a novel neuromodulator, inhibits voltage-gated sodium channels and action potential firing of rat hippocampal neurons[J]. Epilepsy Research, 2009, 83 1: Pages 66-72. DOI: 10.1016/j.eplepsyres.2008.09.006
[4] DO YOUNG KIM. Carisbamate blockade of T-type voltage-gated calcium channels[J]. Epilepsia, 2017, 58 4: 617-626. DOI: 10.1111/epi.13710

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