Vofopitant

Vofopitant
Clinical data
Other names	GR205171; 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	168266-90-8;
PubChem CID	6918331;
IUPHAR/BPS	5752;
ChemSpider	5293535;
UNII	K08BK043YS;
CompTox Dashboard (EPA)	DTXSID10870099 ;
Chemical and physical data
Formula	C21H23F3N6O
Molar mass	432.451 g·mol−1
3D 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, C.J.; Armour, D.R.; Beattie, D.T.; Gale, J.D.; Hawcock, A.B.; Kilpatrick, G.J.; Twissell, D.J.; Ward, P. (1996). "GR205171: A novel antagonist with high affinity for the tachykinin NK1 receptor, and potent broad-spectrum anti-emetic activity". Regulatory Peptides. 65: 45–53. doi:10.1016/0167-0115(96)00071-7.
^ Heldt, Scott A.; Davis, Michael; Ratti, Emiliangelo; Corsi, Mauro; Trist, David; Ressler, Kerry J. (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): 584–595. doi:10.1097/FBP.0b013e32832ec594. PMC 2946835. PMID 19675456.
^ Furmark, Tomas; Appel, Lieuwe; Michelgård, Åsa; Wahlstedt, Kurt; Åhs, Fredrik; Zancan, Stefano; Jacobsson, Eva; Flyckt, Karin; Grohp, Magnus; Bergström, Mats; Pich, Emilio Merlo; Nilsson, Lars-Göran; Bani, Massimo; Långström, Bengt; Fredrikson, Mats (2005). "Cerebral Blood Flow Changes After Treatment of Social Phobia with the Neurokinin-1 Antagonist GR205171, Citalopram, or Placebo". Biological Psychiatry. 58 (2): 132–142. doi:10.1016/j.biopsych.2005.03.029. PMID 16038684.
^ Mathew, Sanjay J.; Vythilingam, Meena; Murrough, James W.; Zarate, Carlos A.; Feder, Adriana; Luckenbaugh, David A.; Kinkead, Becky; Parides, Michael K.; Trist, David G.; Bani, Massimo S.; Bettica, Paolo U.; Ratti, Emiliangelo M.; Charney, Dennis S. (2011). "A selective neurokinin-1 receptor antagonist in chronic PTSD: A randomized, double-blind, placebo-controlled, proof-of-concept trial". European Neuropsychopharmacology. 21 (3): 221–229. doi:10.1016/j.euroneuro.2010.11.012. PMC 3478767. PMID 21194898.

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[1] Gardner, C.J.; Armour, D.R.; Beattie, D.T.; Gale, J.D.; Hawcock, A.B.; Kilpatrick, G.J.; Twissell, D.J.; Ward, P. (1996). "GR205171: A novel antagonist with high affinity for the tachykinin NK1 receptor, and potent broad-spectrum anti-emetic activity". Regulatory Peptides. 65: 45–53. doi:10.1016/0167-0115(96)00071-7.

[2] Heldt, Scott A.; Davis, Michael; Ratti, Emiliangelo; Corsi, Mauro; Trist, David; Ressler, Kerry J. (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): 584–595. doi:10.1097/FBP.0b013e32832ec594. PMC 2946835. PMID 19675456.

[3] Furmark, Tomas; Appel, Lieuwe; Michelgård, Åsa; Wahlstedt, Kurt; Åhs, Fredrik; Zancan, Stefano; Jacobsson, Eva; Flyckt, Karin; Grohp, Magnus; Bergström, Mats; Pich, Emilio Merlo; Nilsson, Lars-Göran; Bani, Massimo; Långström, Bengt; Fredrikson, Mats (2005). "Cerebral Blood Flow Changes After Treatment of Social Phobia with the Neurokinin-1 Antagonist GR205171, Citalopram, or Placebo". Biological Psychiatry. 58 (2): 132–142. doi:10.1016/j.biopsych.2005.03.029. PMID 16038684.

[4] Mathew, Sanjay J.; Vythilingam, Meena; Murrough, James W.; Zarate, Carlos A.; Feder, Adriana; Luckenbaugh, David A.; Kinkead, Becky; Parides, Michael K.; Trist, David G.; Bani, Massimo S.; Bettica, Paolo U.; Ratti, Emiliangelo M.; Charney, Dennis S. (2011). "A selective neurokinin-1 receptor antagonist in chronic PTSD: A randomized, double-blind, placebo-controlled, proof-of-concept trial". European Neuropsychopharmacology. 21 (3): 221–229. doi:10.1016/j.euroneuro.2010.11.012. PMC 3478767. PMID 21194898.

[1]

[2]

[3]

[4]

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

See also

References