Ibipinabant

Ibipinabant
	File:SLV319 CB1 derivative.png
Systematic (IUPAC) name
	4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine
Identifiers
CAS Number	464213-10-3
ATC code	none
PubChem	CID 9826744
Chemical data
Formula	C24H22Cl2N4O2S
Molar mass	501.427[[Script error: No such module "String".]]
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Ibipinabant (SLV-319, 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]

References

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↑ Lange JH, Coolen HK, van Stuivenberg HH, Dijksman JA, Herremans AH, Ronken E, Keizer HG, Tipker K, McCreary AC, Veerman W, Wals HC, Stork B, Verveer PC, den Hartog AP, de Jong NM, Adolfs TJ, Hoogendoorn J, Kruse CG. 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. 2004 Jan 29;47(3):627-43. PMID 14736243
↑ Need AB, Davis RJ, Alexander-Chacko JT, Eastwood B, Chernet E, Phebus LA, Sindelar DK, Nomikos GG. 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 (Berlin). 2006 Jan;184(1):26-35. PMID 16328376
↑ Lange JH, van Stuivenberg HH, Veerman W, Wals HC, Stork B, Coolen HK, McCreary AC, Adolfs TJ, Kruse CG. Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity. Bioorganic and Medicinal Chemistry Letters. 2005 Nov 1;15(21):4794-8. PMID 16140010
↑ Srivastava BK, Joharapurkar A, Raval S, Patel JZ, Soni R, Raval P, Gite A, Goswami A, Sadhwani N, Gandhi N, Patel H, Mishra B, Solanki M, Pandey B, Jain MR, Patel PR. 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. 2007 Nov 29;50(24):5951-66. PMID 17979261
↑ Srivastava BK, Soni R, Joharapurkar A, Sairam KV, Patel JZ, Goswami A, Shedage SA, Kar SS, Salunke RP, Gugale SB, Dhawas A, Kadam P, Mishra B, Sadhwani N, Unadkat VB, Mitra P, Jain MR, Patel PR. 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 and Medicinal Chemistry Letters. 2008 Feb 1;18(3):963-8. PMID 18207393

[1] Lange JH, Coolen HK, van Stuivenberg HH, Dijksman JA, Herremans AH, Ronken E, Keizer HG, Tipker K, McCreary AC, Veerman W, Wals HC, Stork B, Verveer PC, den Hartog AP, de Jong NM, Adolfs TJ, Hoogendoorn J, Kruse CG. 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. 2004 Jan 29;47(3):627-43. PMID 14736243

[2] Need AB, Davis RJ, Alexander-Chacko JT, Eastwood B, Chernet E, Phebus LA, Sindelar DK, Nomikos GG. 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 (Berlin). 2006 Jan;184(1):26-35. PMID 16328376

[3] Lange JH, van Stuivenberg HH, Veerman W, Wals HC, Stork B, Coolen HK, McCreary AC, Adolfs TJ, Kruse CG. Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity. Bioorganic and Medicinal Chemistry Letters. 2005 Nov 1;15(21):4794-8. PMID 16140010

[4] Srivastava BK, Joharapurkar A, Raval S, Patel JZ, Soni R, Raval P, Gite A, Goswami A, Sadhwani N, Gandhi N, Patel H, Mishra B, Solanki M, Pandey B, Jain MR, Patel PR. 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. 2007 Nov 29;50(24):5951-66. PMID 17979261

[5] Srivastava BK, Soni R, Joharapurkar A, Sairam KV, Patel JZ, Goswami A, Shedage SA, Kar SS, Salunke RP, Gugale SB, Dhawas A, Kadam P, Mishra B, Sadhwani N, Unadkat VB, Mitra P, Jain MR, Patel PR. 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 and Medicinal Chemistry Letters. 2008 Feb 1;18(3):963-8. PMID 18207393

[1]

[2]

[3]

[4]

[5]

Ibipinabant

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References

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