CP-122,288

CP-122,288 is a drug which acts as a potent and selective agonist for the 5-HT1B, 5-HT1D and 5-HT1F 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.[1][2][3][4][5]

CP-122,288
Identifiers
IUPAC name
  • N-methyl-1-[3-([(2R)-1-methylpyrrolidin-2-yl]methyl)-1H-indol-5-yl]methanesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H23N3O2S
Molar mass321.44 g·mol−1
3D model (JSmol)
SMILES
  • CNS(=O)(=O)Cc1ccc2c(c1)c(c[nH]2)C[C@H]3CCCN3C
InChI
  • InChI=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
  • Key:BWQZTHPHLITOOZ-CQSZACIVSA-N

See also

References
  1. Lee WS, Moskowitz MA (October 1993). "Conformationally restricted sumatriptan analogues, CP-122,288 and CP-122,638 exhibit enhanced potency against neurogenic inflammation in dura mater". Brain Research. 626 (1–2): 303–5. doi:10.1016/0006-8993(93)90591-a. PMID 8281439. S2CID 9350217.
  2. Beattie DT, Connor HE (April 1995). "The pre- and postjunctional activity of CP-122,288, a conformationally restricted analogue of sumatriptan". European Journal of Pharmacology. 276 (3): 271–6. doi:10.1016/0014-2999(95)00080-5. PMID 7601213.
  3. Waeber C, Moskowitz MA (September 1995). "[3H]sumatriptan labels both 5-HT1D and 5-HT1F receptor binding sites in the guinea pig brain: an autoradiographic study". Naunyn-Schmiedeberg's Archives of Pharmacology. 352 (3): 263–75. doi:10.1007/bf00168556. PMID 8584041. S2CID 8828017.
  4. Gupta P, Brown D, Butler P, Ellis P, Grayson KL, Land GC, et al. (November 1995). "The in vivo pharmacological profile of a 5-HT1 receptor agonist, CP-122,288, a selective inhibitor of neurogenic inflammation". British Journal of Pharmacology. 116 (5): 2385–90. doi:10.1111/j.1476-5381.1995.tb15084.x. PMC 1909056. PMID 8581273.
  5. Roon KI, Olesen J, Diener HC, Ellis P, Hettiarachchi J, Poole PH, Christianssen I, Kleinermans D, Kok JG, Ferrari MD (February 2000). "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". Annals of Neurology. 47 (2): 238–41. doi:10.1002/1531-8249(200002)47:2<238::AID-ANA15>3.0.CO;2-L. PMID 10665496.


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