Dapitant

Structural formula
General
Non-proprietary name	Dapitant
other names	Erispant; RPR 100893; (2 S ) -1 - [(3a S , 4 S , 7a S ) -4-hydroxy-4- (2-methoxyphenyl) -7,7-diphenyl-1,3,3a, 5,6,7a-hexahydroisoindole -2-yl] -2- (2-methoxyphenyl) propan-1-one ( IUPAC );
Molecular formula	C 37 H 39 NO 4
External identifiers / databases
PubChem	132961
ChemSpider	117339
Wikidata	Q1165545
Drug information
Drug class	analgesic
Mechanism of action	NK 1 - antagonist
properties
Molar mass	561.718 g · mol -1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dapitant is a chemical compound that as a potential drug for the treatment of migraine - pain has been developed. After no effectiveness in the acute treatment of migraines could be observed in a clinical study , its further clinical development by the pharmaceutical company Aventis was discontinued. Pharmacologically Dapitant is a neurokinin - antagonist .

Mechanism of action (pharmacodynamics)

As an antagonist, dapitant inhibits the neurokinin NK ₁ receptor . It displaces the body's own ligand substance P from its binding site on the receptor and thereby prevents the effects mediated by substance P. In animal experiments Dapitant acting anti-inflammatory and analgesic . In an animal model of migraines, it also inhibits the release of inflammatory peptides typical of the disease . However, therapeutic efficacy could not be confirmed in clinical studies.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b Diener HC: RPR100893, a substance-P antagonist, is not effective in the treatment of migraine attacks . In: Cephalalgia . 23, No. 3, April 2003, pp. 183-185. PMID 12662184 .
↑ Campbell EA, Gentry C, Patel S, et al. : Oral anti-hyperalgesic and anti-inflammatory activity of NK (1) receptor antagonists in models of inflammatory hyperalgesia of the guinea-pig . In: Pain . 87, No. 3, September 2000, pp. 253-263. PMID 10963905 .
↑ Lee WS, Moussaoui SM, Moskowitz MA: Blockade by oral or parenteral RPR 100893 (a non-peptide NK1 receptor antagonist) of neurogenic plasma protein extravasation within guinea-pig dura mater and conjunctiva . In: Br. J. Pharmacol. . 112, No. 3, July 1994, pp. 920-924. PMID 7921621 . PMC 1910223 (free full text).

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Diener_HC_et_al._(2003)-2] Diener HC: RPR100893, a substance-P antagonist, is not effective in the treatment of migraine attacks . In: Cephalalgia . 23, No. 3, April 2003, pp. 183-185. PMID 12662184 .

[Campbell_EA_et_al._(2000)-3] Campbell EA, Gentry C, Patel S, et al. : Oral anti-hyperalgesic and anti-inflammatory activity of NK (1) receptor antagonists in models of inflammatory hyperalgesia of the guinea-pig . In: Pain . 87, No. 3, September 2000, pp. 253-263. PMID 10963905 .

[Lee_WS_et_al._(1994)-4] Lee WS, Moussaoui SM, Moskowitz MA: Blockade by oral or parenteral RPR 100893 (a non-peptide NK1 receptor antagonist) of neurogenic plasma protein extravasation within guinea-pig dura mater and conjunctiva . In: Br. J. Pharmacol. . 112, No. 3, July 1994, pp. 920-924. PMID 7921621 . PMC 1910223 (free full text).