PF-03550096

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = N-[(1S)-1-(aminocarbonyl)-2,2-dimethylpropyl]-2,3-dihydro-3-(3-hydroxy-3-methylbutyl)-2-oxo-1H-benzimidazole-1-carboxamide

| image = PF-03550096.svg

| image_class = skin-invert-image

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 910376-39-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = E8S33VNW75

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| PubChem = 24857887

| smiles = O=C(N1C(N(CCC(C)(O)C)C2=C1C=CC=C2)=O)N[C@@H](C(C)(C)C)C(N)=O

| StdInChI = 1S/C19H28N4O4/c1-18(2,3)14(15(20)24)21-16(25)23-13-9-7-6-8-12(13)22(17(23)26)11-10-19(4,5)27/h6-9,14,27H,10-11H2,1-5H3,(H2,20,24)(H,21,25)/t14-/m1/s1

| StdInChIKey = GGNIFXBIJCNXCT-CQSZACIVSA-N

| ChemSpiderID = 21378519

| C=19 | H=28 | N=4 | O=4

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PF-03550096 is a drug that acts as a potent agonist for the CB₂ cannabinoid receptor, with good selectivity over CB₁ having K_i values of 7nM at CB₂ and 1500nM at CB₁. It was originally developed by Pfizer in 2008 as a medication for irritable bowel syndrome,{{cite patent | country = WO | number = 2008032164 | pubdate = 20 March 2008 | url = http://patentscope.wipo.int/search/en/detail.jsf?docId=WO2008032164 | inventor = Ando K, et al | assign1 = Pfizer Products Inc. | title = Benzimidazolone Derivatives }} but has only progressed to animal studies.{{cite journal | vauthors = Kikuchi A, Ohashi K, Sugie Y, Sugimoto H, Omura H | title = Pharmacological evaluation of a novel cannabinoid 2 (CB2) ligand, PF-03550096, in vitro and in vivo by using a rat model of visceral hypersensitivity | journal = Journal of Pharmacological Sciences | volume = 106 | issue = 2 | pages = 219–24 | date = February 2008 | pmid = 18270474 | doi = 10.1254/jphs.FP0071599 | doi-access = free }}