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MedKoo Cat#: 530214 | Name: Surinabant

Description:

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

Surinabant, also known as SR-147778, is a cannabinoid CB1 antagonist potentially for the treatment of obesity and alcoholism.

Chemical Structure

Surinabant
Surinabant
CAS#288104-79-0

Theoretical Analysis

MedKoo Cat#: 530214

Name: Surinabant

CAS#: 288104-79-0

Chemical Formula: C23H23BrCl2N4O

Exact Mass: 520.0432

Molecular Weight: 522.27

Elemental Analysis: C, 52.89; H, 4.44; Br, 15.30; Cl, 13.58; N, 10.73; O, 3.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
SR-147778; SR147778; SR 147778
IUPAC/Chemical Name
5-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide
InChi Key
HMXDWDSNPRNUKI-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H23BrCl2N4O/c1-2-18-21(23(31)28-29-12-4-3-5-13-29)27-30(20-11-10-17(25)14-19(20)26)22(18)15-6-8-16(24)9-7-15/h6-11,14H,2-5,12-13H2,1H3,(H,28,31)
SMILES Code
O=C(C1=NN(C2=CC=C(Cl)C=C2Cl)C(C3=CC=C(Br)C=C3)=C1CC)NN4CCCCC4
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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 522.27 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.

Recalculate based on batch purity %
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
1: Klumpers LE, Roy C, Ferron G, Turpault S, Poitiers F, Pinquier JL, van Hasselt JG, Zuurman L, Erwich FA, van Gerven JM. Surinabant, a selective cannabinoid receptor type 1 antagonist, inhibits Δ9-tetrahydrocannabinol-induced central nervous system and heart rate effects in humans. Br J Clin Pharmacol. 2013 Jul;76(1):65-77. doi: 10.1111/bcp.12071. PubMed PMID: 23278647; PubMed Central PMCID: PMC3703229. 2: Tonstad S, Aubin HJ. Efficacy of a dose range of surinabant, a cannabinoid receptor blocker, for smoking cessation: a randomized controlled clinical trial. J Psychopharmacol. 2012 Jul;26(7):1003-9. doi: 10.1177/0269881111431623. PubMed PMID: 22219220. 3: Lamota L, Bermudez-Silva FJ, Marco EM, Llorente R, Gallego A, Rodríguez de Fonseca F, Viveros MP. Effects of adolescent nicotine and SR 147778 (Surinabant) administration on food intake, somatic growth and metabolic parameters in rats. Neuropharmacology. 2008 Jan;54(1):194-205. PubMed PMID: 17720206. 4: Jones EK, Kirkham TC. Noladin ether, a putative endocannabinoid, enhances motivation to eat after acute systemic administration in rats. Br J Pharmacol. 2012 Jul;166(6):1815-21. doi: 10.1111/j.1476-5381.2012.01888.x. PubMed PMID: 22309979; PubMed Central PMCID: PMC3402806. 5: Elrashidi MY, Ebbert JO. Emerging drugs for the treatment of tobacco dependence: 2014 update. Expert Opin Emerg Drugs. 2014 Jun;19(2):243-60. doi: 10.1517/14728214.2014.899580. Review. PubMed PMID: 24654737. 6: Parylak SL, Cottone P, Sabino V, Rice KC, Zorrilla EP. Effects of CB1 and CRF1 receptor antagonists on binge-like eating in rats with limited access to a sweet fat diet: lack of withdrawal-like responses. Physiol Behav. 2012 Sep 10;107(2):231-42. doi: 10.1016/j.physbeh.2012.06.017. PubMed PMID: 22776620; PubMed Central PMCID: PMC3825516. 7: Pamplona FA, Takahashi RN. WIN 55212-2 impairs contextual fear conditioning through the activation of CB1 cannabinoid receptors. Neurosci Lett. 2006 Apr 10-17;397(1-2):88-92. PubMed PMID: 16406322. 8: Pamplona FA, Prediger RD, Pandolfo P, Takahashi RN. The cannabinoid receptor agonist WIN 55,212-2 facilitates the extinction of contextual fear memory and spatial memory in rats. Psychopharmacology (Berl). 2006 Nov;188(4):641-9. PubMed PMID: 16947018. 9: Lallemand F, De Witte P. SR147778, a CB1 cannabinoid receptor antagonist, suppresses ethanol preference in chronically alcoholized Wistar rats. Alcohol. 2006 Jul;39(3):125-34. PubMed PMID: 17127132. 10: Doggrell SA. Will the new CB1 cannabinoid receptor antagonist SR-147778 have advantages over rimonabant? Expert Opin Investig Drugs. 2005 Mar;14(3):339-42. Review. PubMed PMID: 15833065. 11: Janero DR, Makriyannis A. Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis. Expert Opin Emerg Drugs. 2009 Mar;14(1):43-65. doi: 10.1517/14728210902736568 . Review. PubMed PMID: 19249987. 12: Rinaldi-Carmona M, Barth F, Congy C, Martinez S, Oustric D, Pério A, Poncelet M, Maruani J, Arnone M, Finance O, Soubrié P, Le Fur G. SR147778 [5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(1-piperidinyl)-1H-pyrazole-3 -carboxamide], a new potent and selective antagonist of the CB1 cannabinoid receptor: biochemical and pharmacological characterization. J Pharmacol Exp Ther. 2004 Sep;310(3):905-14. PubMed PMID: 15131245. 13: Viveros MP, de Fonseca FR, Bermudez-Silva FJ, McPartland JM. Critical role of the endocannabinoid system in the regulation of food intake and energy metabolism, with phylogenetic, developmental, and pathophysiological implications. Endocr Metab Immune Disord Drug Targets. 2008 Sep;8(3):220-30. Review. PubMed PMID: 18782018. 14: Gessa GL, Serra S, Vacca G, Carai MA, Colombo G. Suppressing effect of the cannabinoid CB1 receptor antagonist, SR147778, on alcohol intake and motivational properties of alcohol in alcohol-preferring sP rats. Alcohol Alcohol. 2005 Jan-Feb;40(1):46-53. PubMed PMID: 15582988.

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