Ibipinabant

Ibipinabant (SLV319, BMS-646,256) was designed by Jos Lange at Solvay Pharmaceuticals in 2000. Nowadays, it is an in vivo active pharmacological tool 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]

ATC code

none

CAS Number

464213-10-3^Y

PubChem CID

9826744

ChemSpider

24765166^N

Quick facts Clinical data, ATC code ...

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	464213-10-3^Y
PubChem CID	9826744
ChemSpider	24765166^N
UNII	O5CSC6WH1T
KEGG	D09349^Y
ChEMBL	ChEMBL158784^N
CompTox Dashboard (EPA)	DTXSID70963572
ECHA InfoCard	100.158.931
Chemical and physical data
Formula	C₂₄H₂₂Cl₂N₄O₂S
Molar mass	501.43 g·mol⁻¹
3D model (JSmol)	Interactive image
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)

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): 627–643. 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): 4794–4798. 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): 5951–5966. 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): 963–968. doi:10.1016/j.bmcl.2007.12.036. PMID 18207393.
[6]
de Bruin NM, Prickaerts J, Lange JH, Akkerman S, Andriambeloson E, de Haan M, et al. (May 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 NM, Lange JH, Kruse CG, Herremans AH, Schoffelmeer AN, van Drimmelen M, De Vries TJ (March 2011). "SLV330, a cannabinoid CB(1) 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 JH, 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.

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