Chemistry:Cilansetron

Short description: Chemical compound

Cilansetron

Clinical data
Other names	Calmactin; KC 9946
Pregnancy category	C
Routes of administration	Oral
ATC code	A03AE03 (WHO)
Legal status
Legal status	Unlicensed
Pharmacokinetic data
Bioavailability	87%
Metabolism	Hepatic
Elimination half-life	1.6 - 1.9 hours
Excretion	Renal
Identifiers
IUPAC name (10R)-10-[(2-Methyl-1H-imidazol-1-yl)methyl]-5,6,9,10-tetrahydro-4H-pyrido(3,2,1-jk)carbazol-11-one
CAS Number	120635-74-7 Y
PubChem CID	6918107
IUPHAR/BPS	2297
ChemSpider	5293321 Y
UNII	2J6DQ1U5B5
KEGG	D03495 Y
ChEMBL	ChEMBL2103778
Chemical and physical data
Formula	C20H21N3O
Molar mass	319.408 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C3c2c1cccc5c1n(c2CC[C@@H]3Cn4ccnc4C)CCC5
InChI InChI=1S/C20H21N3O/c1-13-21-9-11-22(13)12-15-7-8-17-18(20(15)24)16-6-2-4-14-5-3-10-23(17)19(14)16/h2,4,6,9,11,15H,3,5,7-8,10,12H2,1H3/t15-/m1/s1 Y Key:NCNFDKWULDWJDS-OAHLLOKOSA-N Y
(verify)

Cilansetron is an experimental drug that is a 5-HT₃ antagonist under development by Solvay Pharmaceuticals.

5-HT₃ receptors are responsible for causing many things from nausea to excess bowel movements. In conditions such as irritable bowel syndrome (IBS), the receptors have become faulty or oversensitive. 5-HT₃ antagonists work by blocking the nervous and chemical signals from reaching these receptors.

Studies have shown that the drug can improve quality of life in men and women with diarrhea-predominant IBS. Cilansetron is the first 5-HT antagonist specifically designed for IBS that is effective in men as well as women.

In 2005, Solvay received response from the U.S. Food and Drug Administration that cilansertron is not approvable without additional clinical trials; further development has been discontinued.