Ibipinabant

Ibipinabant (SLV319, BMS-646,256) is a drug used in scientific research which acts as a potent and highly selective CB1 antagonist.[1] It has potent anorectic effects in animals,[2] and was researched for the treatment of obesity, although CB1 antagonists as a class have now fallen out of favour as potential anorectics following the problems seen with rimonabant, and so ibipinabant is now only used for laboratory research, especially structure-activity relationship studies into novel CB1 antagonists.[3][4][5] SLV330, which is a structural analogue of Ibipinabant, was reported active in animal models related to the regulation of memory, cognition, as well as in addictive behavior.[6][7] An atom-efficient synthesis of ibipinabant has been reported.[8]

Ibipinabant
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 4S-(−)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.158.931
Chemical and physical data
FormulaC24H22Cl2N4O2S
Molar mass501.427 g·mol−1
3D model (JSmol)
SMILES
  • c2cc(Cl)ccc2C1=NN(C(NC)=NCS(=O)(=O)c3ccc(Cl)cc3)CC1c4ccccc4
InChI
  • InChI=1S/C24H22Cl2N4O2S/c1-27-24(28-16-33(31,32)21-13-11-20(26)12-14-21)30-15-22(17-5-3-2-4-6-17)23(29-30)18-7-9-19(25)10-8-18/h2-14,22H,15-16H2,1H3,(H,27,28)/t22-/m1/s1 N
  • Key:BSFKAVCGRDMWTK-JOCHJYFZSA-N N
 NY (what is this?)  (verify)

See also

References
  1. Lange JH, Coolen HK, van Stuivenberg HH, Dijksman JA, Herremans AH, Ronken E, et al. (January 2004). "Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists". Journal of Medicinal Chemistry. 47 (3): 627–43. doi:10.1021/jm031019q. PMID 14736243.
  2. Need AB, Davis RJ, Alexander-Chacko JT, Eastwood B, Chernet E, Phebus LA, et al. (January 2006). "The relationship of in vivo central CB1 receptor occupancy to changes in cortical monoamine release and feeding elicited by CB1 receptor antagonists in rats". Psychopharmacology. 184 (1): 26–35. doi:10.1007/s00213-005-0234-x. PMID 16328376. S2CID 23402768.
  3. Lange JH, van Stuivenberg HH, Veerman W, Wals HC, Stork B, Coolen HK, et al. (November 2005). "Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity". Bioorganic & Medicinal Chemistry Letters. 15 (21): 4794–8. doi:10.1016/j.bmcl.2005.07.054. PMID 16140010.
  4. Srivastava BK, Joharapurkar A, Raval S, Patel JZ, Soni R, Raval P, et al. (November 2007). "Diaryl dihydropyrazole-3-carboxamides with significant in vivo antiobesity activity related to CB1 receptor antagonism: synthesis, biological evaluation, and molecular modeling in the homology model". Journal of Medicinal Chemistry. 50 (24): 5951–66. doi:10.1021/jm061490u. PMID 17979261.
  5. Srivastava BK, Soni R, Joharapurkar A, Sairam KV, Patel JZ, Goswami A, et al. (February 2008). "Bioisosteric replacement of dihydropyrazole of 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-caboxamidine (SLV-319) a potent CB1 receptor antagonist by imidazole and oxazole". Bioorganic & Medicinal Chemistry Letters. 18 (3): 963–8. doi:10.1016/j.bmcl.2007.12.036. PMID 18207393.
  6. de Bruin, NMWJ; Prickaerts, J; Lange, JHM; Akkerman, S; Andriambeloson, E; de Haan, M; Wijnen, J; van Drimmelen, M; Hissink, E; Heijink, L; Kruse, CG (2010). "SLV330, a cannabinoid CB1 receptor antagonist, ameliorates deficits in the T-maze, object recognition and Social Recognition Tasks in rodents". Neurobiology of Learning and Memory. 93 (4): 522–531. doi:10.1016/j.nlm.2010.01.010. PMID 20132903. S2CID 207261719.
  7. de Bruin, NMWJ; Lange, JHM; Kruse, CG; Herremans, AH; Schoffelmeer, ANM; van Drimmelen, M; De Vries, TJ (2011). "SLV330, a cannabinoid CB1 receptor antagonist, attenuates ethanol and nicotine seeking and improves inhibitory response control in rats". Behavioural Brain Research. 217 (2): 408–415. doi:10.1016/j.bbr.2010.11.013. PMID 21074574. S2CID 205882042.
  8. Lange, JHM; Sanders, HJ; van Rheenen, J (2011). "An expedient atom-efficient synthesis of the cannabinoid CB1 receptor inverse agonist ibipinabant". Tetrahedron Letters. 52 (12): 1303–1305. doi:10.1016/j.tetlet.2011.01.068. ISSN 0040-4039.
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