burapitant

{{Short description|Chemical compound}}

{{Drugbox

| 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

| image = Burapitant_structure.png

| width = 220

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| bioavailability =

| protein_bound =

| metabolism =

| excretion =

| IUPHAR_ligand =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 537034-22-3

| CAS_supplemental =

| ATC_prefix = none

| ATC_suffix =

| PubChem = 23649599

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = E35SK332MS

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL =

| ChemSpiderID = 26519428

| C=31 | H=35 | Cl=2 | F=6 | N=3 | O=3

| 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

| StdInChI = 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

| StdInChIKey = 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.{{cite journal | vauthors = Emonds-Alt X, Proietto V, Steinberg R, Oury-Donat F, Vigé X, Vilain P, Naline E, Daoui S, Advenier C, Le Fur G, Maffrand JP, Soubrié P, Pascal M | display-authors = 6 | title = 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 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 303 | issue = 3 | pages = 1171–9 | date = December 2002 | pmid = 12438541 | doi = 10.1124/jpet.102.040162 | s2cid = 1467606 }}{{cite journal | vauthors = Steinberg R, Alonso R, Rouquier L, Desvignes C, Michaud JC, Cudennec A, Jung M, Simiand J, Griebel G, Emonds-Alt X, Le Fur G, Soubrié P | display-authors = 6 | title = 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 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 303 | issue = 3 | pages = 1180–8 | date = December 2002 | pmid = 12438542 | doi = 10.1124/jpet.102.040279 | s2cid = 286897 }}{{cite journal | vauthors = Pérez S, Tierney A, Deniau JM, Kemel ML | title = 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 | journal = Journal of Neurochemistry | volume = 103 | issue = 6 | pages = 2153–63 | date = December 2007 | pmid = 17949415 | doi = 10.1111/j.1471-4159.2007.04944.x | s2cid = 8099165 | url = https://www.hal.inserm.fr/inserm-00165788/file/Perez_et_al.pdf }} 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.