Vofopitant

Chemical compound

none

Identifiers

IUPAC name

(2S,3S)-N-[(2-Methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]phenyl)methyl]-2-phenylpiperidin-3-amine

CAS Number

168266-90-8

PubChem CID

6918331

IUPHAR/BPS

5752

ChemSpider

5293535

UNII

K08BK043YS

CompTox Dashboard (EPA)

DTXSID10870099

Chemical and physical dataFormulaC₂₁H₂₃F₃N₆OMolar mass432.451 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

COC1=C(C=C(C=C1)N2C(=NN=N2)C(F)(F)F)CN[C@H]3CCCN[C@H]3C4=CC=CC=C4

InChI

InChI=1S/C21H23F3N6O/c1-31-18-10-9-16(30-20(21(22,23)24)27-28-29-30)12-15(18)13-26-17-8-5-11-25-19(17)14-6-3-2-4-7-14/h2-4,6-7,9-10,12,17,19,25-26H,5,8,11,13H2,1H3/t17-,19-/m0/s1
Key:XILNRORTJVDYRH-HKUYNNGSSA-N

Vofopitant (GR205171) is a drug which acts as an NK₁ receptor antagonist. It has antiemetic effects as with other NK₁ antagonists,^[1] and also shows anxiolytic actions in animals.^[2] It was studied for applications such as the treatment of social phobia and post-traumatic stress disorder, but did not prove sufficiently effective to be marketed.^[3]^[4]

References

^ Gardner CJ, Armour DR, Beattie DT, Gale JD, Hawcock AB, Kilpatrick GJ, et al. (August 1996). "GR205171: a novel antagonist with high affinity for the tachykinin NK1 receptor, and potent broad-spectrum anti-emetic activity". Regulatory Peptides. 65 (1): 45–53. doi:10.1016/0167-0115(96)00071-7. PMID 8876035. S2CID 8600542.
^ Heldt SA, Davis M, Ratti E, Corsi M, Trist D, Ressler KJ (October 2009). "Anxiolytic-like effects of the neurokinin 1 receptor antagonist GR-205171 in the elevated plus maze and contextual fear-potentiated startle model of anxiety in gerbils". Behavioural Pharmacology. 20 (7): 584–95. doi:10.1097/FBP.0b013e32832ec594. PMC 2946835. PMID 19675456.
^ Furmark T, Appel L, Michelgård A, Wahlstedt K, Ahs F, Zancan S, et al. (July 2005). "Cerebral blood flow changes after treatment of social phobia with the neurokinin-1 antagonist GR205171, citalopram, or placebo". Biological Psychiatry. 58 (2): 132–42. doi:10.1016/j.biopsych.2005.03.029. PMID 16038684. S2CID 8252615.
^ Mathew SJ, Vythilingam M, Murrough JW, Zarate CA, Feder A, Luckenbaugh DA, et al. (March 2011). "A selective neurokinin-1 receptor antagonist in chronic PTSD: a randomized, double-blind, placebo-controlled, proof-of-concept trial". European Neuropsychopharmacology. 21 (3): 221–9. doi:10.1016/j.euroneuro.2010.11.012. PMC 3478767. PMID 21194898.