Vofopitant

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]

Vofopitant
Clinical data
Other namesGR205171; GR-205171
Routes of
administration		Oral
ATC code
  • none
Identifiers
IUPAC name
  • (2S,3S)-N-[(2-Methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]phenyl)methyl]-2-phenylpiperidin-3-amine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
Chemical and physical data
FormulaC21H23F3N6O
Molar mass432.451 g·mol−1
3D model (JSmol)
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

See also

References
  1. 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.
  2. 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.
  3. 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.
  4. 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.
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