xanomeline   Click here for help

GtoPdb Ligand ID: 57

Synonyms: LY 246708
PDB Ligand
Compound class: Synthetic organic
Comment: Xanomeline is a muscarinic receptor agonist, with preference for the M1 and M4 receptor subtypes [2,7,11]. It also has antagonist activity at 5-HT2 receptors, and agonist activity at 5-HT1 receptors [9]. Xanomeline was investigated for potential to improve cognition in Alzheimer's disease (AD) patients, but activation of muscarinic receptors in the gastrointestinal tract caused severe nausea and diarrhoea, and this adverse effect led to discontinuation of xanomeline's clinical development for AD.
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 3
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 66.49
Molecular weight 281.16
XLogP 3.34
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCCCCCOc1nsnc1C1=CCCN(C1)C
Isomeric SMILES CCCCCCOc1nsnc1C1=CCCN(C1)C
InChI InChI=1S/C14H23N3OS/c1-3-4-5-6-10-18-14-13(15-19-16-14)12-8-7-9-17(2)11-12/h8H,3-7,9-11H2,1-2H3
InChI Key JOLJIIDDOBNFHW-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-(4-hexoxy-1,2,5-thiadiazol-3-yl)-1-methyl-5,6-dihydro-2H-pyridine
International Nonproprietary Names Click here for help
INN number INN
7125 xanomeline
Synonyms Click here for help
LY 246708
Database Links Click here for help
Specialist databases
GPCRdb Ligand xanomeline
Other databases
BindingDB Ligand 50003359
CAS Registry No. 131986-45-3 (source: ChEBI)
ChEBI CHEBI:10056
ChEMBL Ligand CHEMBL21536
DrugCentral Ligand 3652
GtoPdb PubChem SID 135651331
PubChem CID 60809
RCSB PDB Ligand XNO
Search Google for chemical match using the InChIKey JOLJIIDDOBNFHW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JOLJIIDDOBNFHW
Search PubMed clinical trials xanomeline
Search PubMed titles xanomeline
Search PubMed titles/abstracts xanomeline
UniChem Compound Search for chemical match using the InChIKey JOLJIIDDOBNFHW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JOLJIIDDOBNFHW-UHFFFAOYSA-N
Wikipedia Xanomeline