CP-122288

{{Short description|Chemical compound}}

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{{Drugbox

| IUPAC_name = N-methyl-1-[3-([(2R)-1-methylpyrrolidin-2-yl]methyl)-1H-indol-5-yl]methanesulfonamide

| image = CP-122,288 Structure.svg

| width = 220

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| IUPHAR_ligand = 110

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

| CAS_number = 143321-74-8

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

| UNII = 59E9WCT6EM

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| PubChem = 132552

| ChemSpiderID = 117032

| C=16 | H=23 | N=3 | O=2 | S=1

| smiles = CNS(=O)(=O)Cc1ccc2c(c1)c(c[nH]2)C[C@H]3CCCN3C

| StdInChI = 1S/C16H23N3O2S/c1-17-22(20,21)11-12-5-6-16-15(8-12)13(10-18-16)9-14-4-3-7-19(14)2/h5-6,8,10,14,17-18H,3-4,7,9,11H2,1-2H3/t14-/m1/s1

| StdInChIKey = BWQZTHPHLITOOZ-CQSZACIVSA-N

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CP-122,288 is a drug which acts as a potent and selective agonist for the 5-HT_1B, 5-HT_1D and 5-HT_1F serotonin receptor subtypes. It is a derivative of the migraine medication sumatriptan, but while CP-122,288 is 40,000 times more potent than sumatriptan as an inhibitor of neurogenic inflammation and plasma protein extravasation, it is only twice as potent as a constrictor of blood vessels. In human trials, CP-122,288 was not found to be effective as a treatment for migraine, but its selectivity for neurogenic anti-inflammatory action over vasoconstriction has made it useful for research into the underlying causes of migraine.{{cite journal | vauthors = Lee WS, Moskowitz MA | title = Conformationally restricted sumatriptan analogues, CP-122,288 and CP-122,638 exhibit enhanced potency against neurogenic inflammation in dura mater | journal = Brain Research | volume = 626 | issue = 1–2 | pages = 303–5 | date = October 1993 | pmid = 8281439 | doi = 10.1016/0006-8993(93)90591-a | s2cid = 9350217 }}{{cite journal | vauthors = Beattie DT, Connor HE | title = The pre- and postjunctional activity of CP-122,288, a conformationally restricted analogue of sumatriptan | journal = European Journal of Pharmacology | volume = 276 | issue = 3 | pages = 271–6 | date = April 1995 | pmid = 7601213 | doi = 10.1016/0014-2999(95)00080-5 }}{{cite journal | vauthors = Waeber C, Moskowitz MA | title = [3H]sumatriptan labels both 5-HT1D and 5-HT1F receptor binding sites in the guinea pig brain: an autoradiographic study | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 352 | issue = 3 | pages = 263–75 | date = September 1995 | pmid = 8584041 | doi = 10.1007/bf00168556 | s2cid = 8828017 }}{{cite journal | vauthors = Gupta P, Brown D, Butler P, Ellis P, Grayson KL, Land GC, Macor JE, Robson SF, Wythes MJ, Shepperson NB | display-authors = 6 | title = The in vivo pharmacological profile of a 5-HT1 receptor agonist, CP-122,288, a selective inhibitor of neurogenic inflammation | journal = British Journal of Pharmacology | volume = 116 | issue = 5 | pages = 2385–90 | date = November 1995 | pmid = 8581273 | doi = 10.1111/j.1476-5381.1995.tb15084.x | pmc = 1909056 }}{{cite journal | vauthors = Roon KI, Olesen J, Diener HC, Ellis P, Hettiarachchi J, Poole PH, Christianssen I, Kleinermans D, Kok JG, Ferrari MD | title = No acute antimigraine efficacy of CP-122,288, a highly potent inhibitor of neurogenic inflammation: results of two randomized, double-blind, placebo-controlled clinical trials | journal = Annals of Neurology | volume = 47 | issue = 2 | pages = 238–41 | date = February 2000 | pmid = 10665496 | doi = 10.1002/1531-8249(200002)47:2<238::AID-ANA15>3.0.CO;2-L | s2cid = 41069269 }}