Burapitant

Burapitant
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-[1-[2-[(2R)-4-[2-[3,5-bis(trifluoromethyl)phenyl]acetyl]-2-(3,4-dichlorophenyl)morpholin-2-yl]ethyl]piperidin-4-yl]-2-methylpropanamide;
CAS Number	537034-22-3 ;
PubChem CID	23649599;
ChemSpider	26519428;
UNII	E35SK332MS;
CompTox Dashboard (EPA)	DTXSID10968465 ;
Chemical and physical data
Formula	C31H35Cl2F6N3O3
Molar mass	682.53 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C1CCN(CC1)CC[C@]2(CN(CCO2)C(=O)CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC(=C(C=C4)Cl)Cl)C(=O)N;
	InChI InChI=1S/C31H35Cl2F6N3O3/c1-28(2,27(40)44)20-5-8-41(9-6-20)10-7-29(21-3-4-24(32)25(33)17-21)18-42(11-12-45-29)26(43)15-19-13-22(30(34,35)36)16-23(14-19)31(37,38)39/h3-4,13-14,16-17,20H,5-12,15,18H2,1-2H3,(H2,40,44)/t29-/m0/s1; Key:ZLNYUCXXSDDIFU-LJAQVGFWSA-N;

Burapitant (SSR-240,600) is a drug developed by Sanofi-Aventis which was one of the first compounds developed that acts as a potent and selective antagonist for the NK₁ receptor.^[1]^[2]^[3] While burapitant itself did not proceed beyond early clinical trials and was never developed for clinical use in humans, promising animal results from this and related compounds have led to a number of novel drugs from this class that have now been introduced into medical use.

References

^ Emonds-Alt X, Proietto V, Steinberg R, Oury-Donat F, Vigé X, Vilain P, et al. (December 2002). "SSR240600 [(R)-2-(1-[2-[4-[2-[3,5-bis(trifluoromethyl)phenyl]acetyl]-2-(3,4-dichlorophenyl)-2-morpholinyl]ethyl]- 4-piperidinyl)-2-methylpropanamide], a centrally active nonpeptide antagonist of the tachykinin neurokinin-1 receptor: I. biochemical and pharmacological characterization". The Journal of Pharmacology and Experimental Therapeutics. 303 (3): 1171–9. doi:10.1124/jpet.102.040162. PMID 12438541. S2CID 1467606.
^ Steinberg R, Alonso R, Rouquier L, Desvignes C, Michaud JC, Cudennec A, et al. (December 2002). "SSR240600 [(R)-2-(1-[2-[4-[2-[3,5-bis(trifluoromethyl)phenyl]acetyl]-2-(3,4-dichlorophenyl)-2-morpholinyl]ethyl]-4-piperidinyl)-2-methylpropanamide], a centrally active nonpeptide antagonist of the tachykinin neurokinin 1 receptor: II. Neurochemical and behavioral characterization". The Journal of Pharmacology and Experimental Therapeutics. 303 (3): 1180–8. doi:10.1124/jpet.102.040279. PMID 12438542. S2CID 286897.
^ Pérez S, Tierney A, Deniau JM, Kemel ML (December 2007). "Tachykinin regulation of cholinergic transmission in the limbic/prefrontal territory of the rat dorsal striatum: implication of new neurokinine 1-sensitive receptor binding site and interaction with enkephalin/mu opioid receptor transmission" (PDF). Journal of Neurochemistry. 103 (6): 2153–63. doi:10.1111/j.1471-4159.2007.04944.x. PMID 17949415. S2CID 8099165.

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[1] Emonds-Alt X, Proietto V, Steinberg R, Oury-Donat F, Vigé X, Vilain P, et al. (December 2002). "SSR240600 [(R)-2-(1-[2-[4-[2-[3,5-bis(trifluoromethyl)phenyl]acetyl]-2-(3,4-dichlorophenyl)-2-morpholinyl]ethyl]- 4-piperidinyl)-2-methylpropanamide], a centrally active nonpeptide antagonist of the tachykinin neurokinin-1 receptor: I. biochemical and pharmacological characterization". The Journal of Pharmacology and Experimental Therapeutics. 303 (3): 1171–9. doi:10.1124/jpet.102.040162. PMID 12438541. S2CID 1467606.

[2] Steinberg R, Alonso R, Rouquier L, Desvignes C, Michaud JC, Cudennec A, et al. (December 2002). "SSR240600 [(R)-2-(1-[2-[4-[2-[3,5-bis(trifluoromethyl)phenyl]acetyl]-2-(3,4-dichlorophenyl)-2-morpholinyl]ethyl]-4-piperidinyl)-2-methylpropanamide], a centrally active nonpeptide antagonist of the tachykinin neurokinin 1 receptor: II. Neurochemical and behavioral characterization". The Journal of Pharmacology and Experimental Therapeutics. 303 (3): 1180–8. doi:10.1124/jpet.102.040279. PMID 12438542. S2CID 286897.

[3] Pérez S, Tierney A, Deniau JM, Kemel ML (December 2007). "Tachykinin regulation of cholinergic transmission in the limbic/prefrontal territory of the rat dorsal striatum: implication of new neurokinine 1-sensitive receptor binding site and interaction with enkephalin/mu opioid receptor transmission" (PDF). Journal of Neurochemistry. 103 (6): 2153–63. doi:10.1111/j.1471-4159.2007.04944.x. PMID 17949415. S2CID 8099165.

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v t e Neurokinin receptor modulators
NK₁	Agonists: Substance P Antagonists: Aprepitant Befetupitant Burapitant Casopitant CI-1021 CP-96345 CP-99994 CP-122721 Dapitant Elinzanetant Ezlopitant Figopitant FK-888 Fosaprepitant Fosnetupitant GR-203040 GW-597599 HSP-117 L-733,060 L-741,671 L-743,310 L-758,298 Lanepitant LY-306740 Maropitant Netupitant NKP-608 Nolpitantium besilate Orvepitant Rolapitant RP-67580 SDZ NKT 343 Serlopitant T-2328 Telmapitant Tradipitant Vestipitant Vofopitant
NK₂	Agonists: Neurokinin A Antagonists: GR-159897 Ibodutant Nepadutant Saredutant
NK₃	Agonists: Neurokinin B Senktide Antagonists: Elinzanetant Fezolinetant Osanetant Pavinetant SB-218,795 SB-222,200 Talnetant