(R)-Carisbamate | 194085-74-0 | Carisbamate isomer

MedKoo Cat#: 330218 | Name: (R)-Carisbamate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

(R)-Carisbamate is the R-isomer of Carisbamate. Carisbamate (YKP 509, proposed trade name Comfyde) is an experimental anticonvulsant drug that was under development by Johnson & Johnson Pharmaceutical Research and Development but never marketed.

Chemical Structure

(R)-Carisbamate

CAS#194085-74-0 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 330218

Name: (R)-Carisbamate

CAS#: 194085-74-0 (R-isomer)

Chemical Formula: C9H10ClNO3

Exact Mass: 215.0349

Molecular Weight: 215.63

Elemental Analysis: C, 50.13; H, 4.67; Cl, 16.44; N, 6.50; O, 22.26

Price and Availability

Size	Price	Availability
10mg	USD 190.00	Ready to ship
25mg	USD 350.00	Ready to ship
50mg	USD 550.00	Ready to ship
100mg	USD 950.00	Ready to ship
200mg	USD 1,650.00	Ready to ship
500mg	USD 2,650.00	Ready to ship

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Related CAS #

194085-75-1 (S-isomer) 194085-74-0 (R-isomer)

Synonym

(R)-Carisbamate; (R)-YKP-509; (R)-YKP509; (R)-YKP 509;

IUPAC/Chemical Name

(1R)-1-(2-Chlorophenyl)-1,2-ethanediol 2-Carbamate

InChi Key

OLBWFRRUHYQABZ-QMMMGPOBSA-N

InChi Code

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-/m0/s1

SMILES Code

O[C@H](C1=CC=CC=C1Cl)COC(N)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C21R12B15

QC Data

View QC data: current batch, Lot#C21R12B15

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Carisbamate is a novel neurotherapeutic drug.

In vitro activity:

TBD

In vivo activity:

The efficacy of carisbamate was tested to suppress spasms in the multiple-hit rat model of SIS. Sprague-Dawley rats received right intracerebral infusions of doxorubicin and lipopolysaccharide at postnatal day 3 (PN3) and intraperitoneal p-chlorophenylalanine at PN5. A single intraperitoneal injection of carisbamate was administered at PN4. Carisbamate acutely reduced both behavioral spasms (CRS-30 and CRS-60 groups only) and electroclinical spasms during the first 2-3 postinjection hours, without detectable toxicity or mortality. The findings provide preclinical evidence that carisbamate displays acute anticonvulsive effect on spasms through a sodium channel-independent mechanism. Because spasms in the multiple-hit rat model are refractory to ACTH and transiently sensitive to vigabatrin, carisbamate may constitute a candidate new therapy for SIS, including the ACTH-refractory spasms. Reference: Epilepsia. 2011 Sep;52(9):1678-84. https://pubmed.ncbi.nlm.nih.gov/21770922/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 215.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Ono T, Moshé SL, Galanopoulou AS. Carisbamate acutely suppresses spasms in a rat model of symptomatic infantile spasms. Epilepsia. 2011 Sep;52(9):1678-84. doi: 10.1111/j.1528-1167.2011.03173.x. Epub 2011 Jul 19. PMID: 21770922; PMCID: PMC3169712.

In vitro protocol:

In vivo protocol:

TBD

1: Bhamidipati RK, Mullangi R, Srinivas NR. Interspecies scaling of urinary excretory amounts of nine drugs belonging to different therapeutic areas with diverse chemical structures - accurate prediction of the human urinary excretory amounts. Xenobiotica. 2017 Feb;47(2):112-118. doi: 10.3109/00498254.2016.1166290. Epub 2016 Apr 19. PubMed PMID: 27093131. 2: Galanopoulou AS. Basic mechanisms of catastrophic epilepsy -- overview from animal models. Brain Dev. 2013 Sep;35(8):748-56. doi: 10.1016/j.braindev.2012.12.005. Epub 2013 Jan 11. Review. PubMed PMID: 23312951; PubMed Central PMCID: PMC3644363. 3: Rezvani AH, Lawrence AJ, Arolfo MP, Levin ED, Overstreet DH. Novel medication targets for the treatment of alcoholism: preclinical studies. Recent Pat CNS Drug Discov. 2012 Aug;7(2):151-62. Review. PubMed PMID: 22574676. 4: Gonzalez M, Zannikos P, DiBernardo A, Brashear HR, Ariyawansa J. Effect of carisbamate on the pharmacokinetics and pharmacodynamics of warfarin in healthy participants. J Clin Pharmacol. 2012 Sep;52(9):1420-9. doi: 10.1177/0091270011415412. Epub 2011 Oct 19. PubMed PMID: 22011511. 5: Ono T, Moshé SL, Galanopoulou AS. Carisbamate acutely suppresses spasms in a rat model of symptomatic infantile spasms. Epilepsia. 2011 Sep;52(9):1678-84. doi: 10.1111/j.1528-1167.2011.03173.x. Epub 2011 Jul 19. PubMed PMID: 21770922; PubMed Central PMCID: PMC3169712. 6: Bialer M, Johannessen SI, Levy RH, Perucca E, Tomson T, White HS. Progress report on new antiepileptic drugs: a summary of the Tenth Eilat Conference (EILAT X). Epilepsy Res. 2010 Dec;92(2-3):89-124. doi: 10.1016/j.eplepsyres.2010.09.001. Review. PubMed PMID: 20970964. 7: Bialer M, Johannessen SI, Levy RH, Perucca E, Tomson T, White HS. Progress report on new antiepileptic drugs: a summary of the Ninth Eilat Conference (EILAT IX). Epilepsy Res. 2009 Jan;83(1):1-43. doi: 10.1016/j.eplepsyres.2008.09.005. Epub 2008 Nov 12. PubMed PMID: 19008076. 8: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Sep;29(7):467-509. PubMed PMID: 17982511. 9: Mannens GS, Hendrickx J, Janssen CG, Chien S, Van Hoof B, Verhaeghe T, Kao M, Kelley MF, Goris I, Bockx M, Verreet B, Bialer M, Meuldermans W. The absorption, metabolism, and excretion of the novel neuromodulator RWJ-333369 (1,2-ethanediol, [1-2-chlorophenyl]-, 2-carbamate, [S]-) in humans. Drug Metab Dispos. 2007 Apr;35(4):554-65. Epub 2006 Aug 25. PubMed PMID: 16936066.