ibipinabant

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 407395176

| IUPAC_name = 4S-(−)-3-(4-chlorophenyl)-N-methyl-N{{'}}-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine

| image = Ibipinabant.svg

| width = 250

| tradename =

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| routes_of_administration =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 464213-10-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 9826744

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = O5CSC6WH1T

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D09349

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 158784

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 24765166

| chemical_formula =

| C=24 | H=22 | Cl=2 | N=4 | O=2 | S=1

| smiles = c2cc(Cl)ccc2C1=NN(C(NC)=NCS(=O)(=O)c3ccc(Cl)cc3)CC1c4ccccc4

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = BSFKAVCGRDMWTK-JOCHJYFZSA-N

}}

Ibipinabant (SLV319, BMS-646,256) is a drug used in scientific research which acts as a potent and highly selective CB₁ antagonist.{{cite journal | vauthors = 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 | display-authors = 6 | title = Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists | journal = Journal of Medicinal Chemistry | volume = 47 | issue = 3 | pages = 627–643 | date = January 2004 | pmid = 14736243 | doi = 10.1021/jm031019q }} It has potent anorectic effects in animals,{{cite journal | vauthors = Need AB, Davis RJ, Alexander-Chacko JT, Eastwood B, Chernet E, Phebus LA, Sindelar DK, Nomikos GG | display-authors = 6 | title = The relationship of in vivo central CB1 receptor occupancy to changes in cortical monoamine release and feeding elicited by CB1 receptor antagonists in rats | journal = Psychopharmacology | volume = 184 | issue = 1 | pages = 26–35 | date = January 2006 | pmid = 16328376 | doi = 10.1007/s00213-005-0234-x | s2cid = 23402768 }} 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.{{cite journal | vauthors = Lange JH, van Stuivenberg HH, Veerman W, Wals HC, Stork B, Coolen HK, McCreary AC, Adolfs TJ, Kruse CG | display-authors = 6 | title = Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity | journal = Bioorganic & Medicinal Chemistry Letters | volume = 15 | issue = 21 | pages = 4794–4798 | date = November 2005 | pmid = 16140010 | doi = 10.1016/j.bmcl.2005.07.054 }}{{cite journal | vauthors = 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 | display-authors = 6 | title = 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 = Journal of Medicinal Chemistry | volume = 50 | issue = 24 | pages = 5951–5966 | date = November 2007 | pmid = 17979261 | doi = 10.1021/jm061490u }}{{cite journal | vauthors = 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 | display-authors = 6 | title = 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 | journal = Bioorganic & Medicinal Chemistry Letters | volume = 18 | issue = 3 | pages = 963–968 | date = February 2008 | pmid = 18207393 | doi = 10.1016/j.bmcl.2007.12.036 }} 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.{{cite journal | vauthors = de Bruin NM, Prickaerts J, Lange JH, Akkerman S, Andriambeloson E, de Haan M, Wijnen J, van Drimmelen M, Hissink E, Heijink L, Kruse CG | display-authors = 6 | title = SLV330, a cannabinoid CB1 receptor antagonist, ameliorates deficits in the T-maze, object recognition and Social Recognition Tasks in rodents | journal = Neurobiology of Learning and Memory | volume = 93 | issue = 4 | pages = 522–531 | date = May 2010 | pmid = 20132903 | doi = 10.1016/j.nlm.2010.01.010 | s2cid = 207261719 }}{{cite journal | vauthors = de Bruin NM, Lange JH, Kruse CG, Herremans AH, Schoffelmeer AN, van Drimmelen M, De Vries TJ | title = SLV330, a cannabinoid CB(1) receptor antagonist, attenuates ethanol and nicotine seeking and improves inhibitory response control in rats | journal = Behavioural Brain Research | volume = 217 | issue = 2 | pages = 408–415 | date = March 2011 | pmid = 21074574 | doi = 10.1016/j.bbr.2010.11.013 | s2cid = 205882042 }} An atom-efficient synthesis of ibipinabant has been reported.{{Cite journal| vauthors = Lange JH, Sanders HJ, van Rheenen J |date=2011|title=An expedient atom-efficient synthesis of the cannabinoid CB1 receptor inverse agonist ibipinabant |journal=Tetrahedron Letters |volume=52 |issue=12 |pages=1303–1305 |doi=10.1016/j.tetlet.2011.01.068 }}