cerlapirdine   Click here for help

GtoPdb Ligand ID: 7356

Synonyms: PF-05212365 | SAM-531 | WAY-262531
Compound class: Synthetic organic
Comment: Cerlapirdine is a Wyeth/Pfizer selective 5-HT6 receptor antagonist for the treatment of cognitive disorders associated with Alzheimer's disease and schizophrenia [2] . Since the phase 2 trial was stopped development may have ceased. Note, unusually, this INN is PubMed-negative so you will need to search the synonyms to find publications. The hydrochloride salt is CID 53385647.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 83.67
Molecular weight 409.15
XLogP 4.84
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CN(CCCOc1ccc2c(c1)c([nH]n2)S(=O)(=O)c1cccc2c1cccc2)C
Isomeric SMILES CN(CCCOc1ccc2c(c1)c([nH]n2)S(=O)(=O)c1cccc2c1cccc2)C
InChI InChI=1S/C22H23N3O3S/c1-25(2)13-6-14-28-17-11-12-20-19(15-17)22(24-23-20)29(26,27)21-10-5-8-16-7-3-4-9-18(16)21/h3-5,7-12,15H,6,13-14H2,1-2H3,(H,23,24)
1. Bernotas, Ronald Charles et al.. (2007)
Substituted-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands.
Patent number: WO2007021711. Assignee: Wyeth (now Pfizer). Priority date: 15/08/2005. Publication date: 22/02/2007.
2. Codony X, Vela JM, Ramírez MJ. (2011)
5-HT(6) receptor and cognition.
Curr Opin Pharmacol, 11 (1): 94-100. [PMID:21330210]
3. Commery TA. (2010)
SAM-531, N,N-dimethyl-3-{[3-(1-naphthylsulfonyl)-1H-indazol-5-yl]oxy} propan-1-amine, a novel serotonin-6 receptor antagonist with preclinical pro-cognitive efficacy.
Alzheimers Dement, 6 (4): S548-S549.