CP-122,288

CP-122,288
Identifiers
	IUPAC name N-methyl-1-[3-([(2R)-1-methylpyrrolidin-2-yl]methyl)-1H-indol-5-yl]methanesulfonamide;
CAS Number	143321-74-8;
PubChem CID	132552;
IUPHAR/BPS	110;
ChemSpider	117032;
CompTox Dashboard (EPA)	DTXSID00931820 ;
Chemical and physical data
Formula	C16H23N3O2S
Molar mass	321.437 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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;

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.^[1]^[2]^[3]^[4]^[5]

References

^ Lee WS, Moskowitz MA. Conformationally restricted sumatriptan analogues, CP-122,288 and CP-122,638 exhibit enhanced potency against neurogenic inflammation in dura mater. Brain Res. 1993 Oct 29;626(1-2):303-5. PMID 8281439
^ Beattie DT, Connor HE. The pre- and postjunctional activity of CP-122,288, a conformationally restricted analogue of sumatriptan. Eur J Pharmacol. 1995 Apr 4;276(3):271-6. PMID 7601213
^ Waeber C, Moskowitz MA. [3H]sumatriptan labels both 5-HT1D and 5-HT1F receptor binding sites in the guinea pig brain: an autoradiographic study. Naunyn Schmiedebergs Arch Pharmacol. 1995 Sep;352(3):263-75. PMID 8584041
^ Gupta P, Brown D, Butler P, Ellis P, Grayson KL, Land GC, Macor JE, Robson SF, Wythes MJ, Shepperson NB. The in vivo pharmacological profile of a 5-HT1 receptor agonist, CP-122,288, a selective inhibitor of neurogenic inflammation. Br J Pharmacol. 1995 Nov;116(5):2385-90. PMID 8581273
^ Roon KI, Olesen J, Diener HC, Ellis P, Hettiarachchi J, Poole PH, Christianssen I, Kleinermans D, Kok JG, Ferrari MD. 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. Ann Neurol. 2000 Feb;47(2):238-41. PMID 10665496

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[1] Lee WS, Moskowitz MA. Conformationally restricted sumatriptan analogues, CP-122,288 and CP-122,638 exhibit enhanced potency against neurogenic inflammation in dura mater. Brain Res. 1993 Oct 29;626(1-2):303-5. PMID 8281439

[2] Beattie DT, Connor HE. The pre- and postjunctional activity of CP-122,288, a conformationally restricted analogue of sumatriptan. Eur J Pharmacol. 1995 Apr 4;276(3):271-6. PMID 7601213

[3] Waeber C, Moskowitz MA. [3H]sumatriptan labels both 5-HT1D and 5-HT1F receptor binding sites in the guinea pig brain: an autoradiographic study. Naunyn Schmiedebergs Arch Pharmacol. 1995 Sep;352(3):263-75. PMID 8584041

[4] Gupta P, Brown D, Butler P, Ellis P, Grayson KL, Land GC, Macor JE, Robson SF, Wythes MJ, Shepperson NB. The in vivo pharmacological profile of a 5-HT1 receptor agonist, CP-122,288, a selective inhibitor of neurogenic inflammation. Br J Pharmacol. 1995 Nov;116(5):2385-90. PMID 8581273

[5] Roon KI, Olesen J, Diener HC, Ellis P, Hettiarachchi J, Poole PH, Christianssen I, Kleinermans D, Kok JG, Ferrari MD. 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. Ann Neurol. 2000 Feb;47(2):238-41. PMID 10665496

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See also

References