asimadoline   

GtoPdb Ligand ID: 9279

Synonyms: EMD 61 753 [1] | EMD 61753 | EMD-61753
Compound class: Synthetic organic
Comment: Asimadoline is an orally active, selective kappa-opioid receptor agonist. It exhibits little blood-brain barrier penetrance so is considered peripherally acting. Asimadoline has demonstrated efficacy in several preclinical pruritus models, and has been investigated as a therapy for irritable bowel syndrome.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 43.78
Molecular weight 414.23
XLogP 4.19
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC1CCN(C1)CC(N(C(=O)C(c1ccccc1)c1ccccc1)C)c1ccccc1
Isomeric SMILES O[C@H]1CCN(C1)C[C@@H](N(C(=O)C(c1ccccc1)c1ccccc1)C)c1ccccc1
InChI InChI=1S/C27H30N2O2/c1-28(25(21-11-5-2-6-12-21)20-29-18-17-24(30)19-29)27(31)26(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,24-26,30H,17-20H2,1H3/t24-,25+/m0/s1
InChI Key JHLHNYVMZCADTC-LOSJGSFVSA-N
Classification
Compound class Synthetic organic
IUPAC Name
N-[(1S)-2-[(3S)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-di(phenyl)acetamide
International Nonproprietary Names
INN number INN
7459 asimadoline
Synonyms
EMD 61 753 [1] | EMD 61753 | EMD-61753
Database Links
BindingDB Ligand 50366356
CAS Registry No. 153205-46-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL1190199
DrugBank Ligand DB05104
GtoPdb PubChem SID 318164798
PubChem CID 179340
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