Casopitant

Casopitant (INNTooltip International Nonproprietary Name),^[1]: 208 former tentative trade names Rezonic (U.S.) and Zunrisa (Europe), is an NK₁ receptor antagonist which was undergoing research for the treatment of chemotherapy-induced nausea and vomiting.^[2][3] It was under development by GlaxoSmithKline.^[2] In July 2008, the company filed a marketing authorisation application with the European Medicines Agency. The application was withdrawn and development was discontinued in September 2009 because GlaxoSmithKline decided that further safety assessment was necessary.^[2][4] However, a 2022 review listed casopitant as under development as a potential novel antidepressant for the treatment of major depressive disorder, with a phase 2 clinical trial having been completed.^[5]

Casopitant

Clinical data
Other names	GW679769; GW-679769; (2R,4S)-4-(4-Acetylpiperazin-1-yl)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methylpiperidine-1-carboxamide
ATC code	A04AD13 (WHO)
Identifiers
IUPAC name (2S,4S)-4-(4-Acetyl-1-piperazinyl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methyl-1-piperidinecarboxamide
CAS Number	414910-27-3
PubChem CID	23725089
ChemSpider	25069049
UNII	3B03KPM27L
KEGG	D06574
ChEMBL	ChEMBL2107320
CompTox Dashboard (EPA)	DTXSID40961762
Chemical and physical data
Formula	C30H35F7N4O2
Molar mass	616.625 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C=CC(=C1)F)[C@@H]2C[C@H](CCN2C(=O)N(C)[C@H](C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN(CC4)C(=O)C
InChI InChI=1S/C30H35F7N4O2/c1-18-13-24(31)5-6-26(18)27-17-25(40-11-9-39(10-12-40)20(3)42)7-8-41(27)28(43)38(4)19(2)21-14-22(29(32,33)34)16-23(15-21)30(35,36)37/h5-6,13-16,19,25,27H,7-12,17H2,1-4H3/t19-,25-,27+/m1/s1 Key:XGGTZCKQRWXCHW-JRLVAEJTSA-N
(verify)

References

1. "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List56" (PDF). World Health Organization. 2006. Retrieved 17 November 2016.
2. Name, Drug (25 December 2021). "Casopitant". AdisInsight. Retrieved 21 August 2022.
3. Lohr L (2008). "Chemotherapy-induced nausea and vomiting". Cancer Journal. 14 (2): 85–93. doi:10.1097/PPO.0b013e31816a0f07. PMID 18391612. S2CID 43224257.
4. "GlaxoSmithKline withdraws its marketing authorisation application for Zunrisa" (PDF). London: EMEA. 13 October 2009. Archived from the original (PDF) on 15 October 2009. Retrieved 21 December 2009.
5. Sakurai H, Yonezawa K, Tani H, Mimura M, Bauer M, Uchida H (July 2022). "Novel Antidepressants in the Pipeline (Phase II and III): A Systematic Review of the US Clinical Trials Registry". Pharmacopsychiatry. 55 (4): 193–202. doi:10.1055/a-1714-9097. PMC 9259184. PMID 35045580.