Vofopitant

• CAT Number: I010039
• CAS Number: 168266-90-8
• Molecular Formula: C21H23F3N6O
• Molecular Weight: 432.451
• Purity: ≥95%
• Target: NK1 receptor antagonist
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4 °C for short term, or -20 °C for long term
• IUPAC Name: (2S,3S)-N-[[2-methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]phenyl]methyl]-2-phenylpiperidin-3-amine
• 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
• InChIKey: XILNRORTJVDYRH-HKUYNNGSSA-N
• SMILES: COC1=C(C=C(C=C1)N2C(=NN=N2)C(F)(F)F)CNC3CCCNC3C4=CC=CC=C4

Vofopitant (also known as GR-205,171) is an NK1 receptor antagonist. It has antiemetic effects as with other NK1 antagonists, and also shows anxiolytic actions in animals. It was trialled for applications such as the treatment of social phobia and post-traumatic stress disorder, but did not prove sufficiently effective to be marketed.

Reference

1:Renoldi G, Invernizzi RW. Blockade of tachykinin NK1 receptors attenuates stress-induced rise of extracellular noradrenaline and dopamine in the rat and gerbil medial prefrontal cortex. J Neurosci Res. 2006 Oct;84(5):961-8. PubMed PMID: 16862563.
2:Gannon RL, Millan MJ. The selective tachykinin neurokinin 1 (NK1) receptor antagonist, GR 205,171, stereospecifically inhibits light-induced phase advances of hamster circadian activity rhythms. Eur J Pharmacol. 2005 Dec 19;527(1-3):86-93. Epub 2005 Nov 22. PubMed PMID: 16307740.
3:Serres F, Sartori SB, Halton A, Pei Q, Rochat C, Singewald N, Sharp T, Millan MJ. Stereoselective and region-specific induction of immediate early gene expression in rat parietal cortex by blockade of neurokinin 1 receptors. J Psychopharmacol. 2006 Jul;20(4):570-6. Epub 2005 Oct 4. Erratum in: J Psychopharmacol. 2011 Jun;25(6):853. Millan, Mark [corrected to Millan, Mark J]. PubMed PMID: 16204322.