Cinanserin

Cinanserin
Clinical data
ATC code	none;
Identifiers
	IUPAC name (2E)-N-(2-{[3-(dimethylamino)propyl]thio}phenyl)-3-phenylacrylamide;
CAS Number	1166-34-3 ;
PubChem CID	5475158;
ChemSpider	4584027 ;
UNII	KI6J9OY7A3;
ChEBI	CHEBI:145999;
ChEMBL	ChEMBL18786 ;
CompTox Dashboard (EPA)	DTXSID30859588 DTXSID7045653, DTXSID30859588 ;
ECHA InfoCard	100.220.552
Chemical and physical data
Formula	C20H24N2OS
Molar mass	340.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CCCSC1=CC=CC=C1NC(=O)\C=C\C2=CC=CC=C2;
	InChI InChI=1S/C20H24N2OS/c1-22(2)15-8-16-24-19-12-7-6-11-18(19)21-20(23)14-13-17-9-4-3-5-10-17/h3-7,9-14H,8,15-16H2,1-2H3,(H,21,23)/b14-13+ ; Key:RSUVYMGADVXGOU-BUHFOSPRSA-N ;
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Cinanserin (INN) is a 5-HT_2A/5-HT_2C receptor antagonist discovered in the 1960s.^[1]^[2] It has about 50-fold higher affinity for the 5-HT_2A receptor than for 5-HT_2C, and very low affinity for 5-HT₁ receptors.^[2]

Cinanserin also inhibits the 3C-like protease of SARS-CoV-1^[3] and SARS-CoV-2,^[4] but with much lower affinity.

References

^ Neuman RS, Zebrowska G (December 1992). "Serotonin (5-HT2) receptor mediated enhancement of cortical unit activity". Canadian Journal of Physiology and Pharmacology. 70 (12): 1604–9. doi:10.1139/y92-230. PMID 1301238.
^ ^a ^b Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
^ Chen L, Gui C, Luo X, Yang Q, Günther S, Scandella E, et al. (June 2005). "Cinanserin is an inhibitor of the 3C-like proteinase of severe acute respiratory syndrome coronavirus and strongly reduces virus replication in vitro". Journal of Virology. 79 (11): 7095–103. doi:10.1128/JVI.79.11.7095-7103.2005. PMC 1112131. PMID 15890949.
^ Jin Z, Du X, Xu Y, Deng Y, Liu M, Zhao Y, Zhang B, Li X, Zhang L, Peng C, Duan Y, Yu J, Wang L, Yang K, Liu F, Jiang R, Yang X, You T, Liu X, Yang X, Bai F, Liu H, Liu X, Guddat LW, Xu W, Xiao G, Qin C, Shi Z, Jiang H, Rao Z, Yang H (June 2020). "Structure of Mpro from SARS-CoV-2 and discovery of its inhibitors". Nature. 582 (7811): 289–293. doi:10.1038/s41586-020-2223-y. PMID 32272481. Cinanserin is an inhibitor of SARS-CoV-2 Mpro.

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