| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H30N2O2 |
| Molecular Weight | 414.5393 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN([C@H](CN1CC[C@H](O)C1)C2=CC=CC=C2)C(=O)C(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=JHLHNYVMZCADTC-LOSJGSFVSA-N
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
| Molecular Formula | C27H30N2O2 |
| Molecular Weight | 414.5393 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Asimadoline is an orally active, highly selective kappa-opioid receptor agonist with approximately 500-fold greater affinity for human kappa-, as compared with either delta- or mu-opioid receptors. Due to its high selectivity for the kappa-opioid receptor, asimadoline does not produce mu-opioid like side effects. It is investigated for use/treatment in irritable bowel syndrome, pruritus, postoperative ileus. A drug interaction study investigating the coadministration of asimadoline with ketoconazole was performed in healthy volunteers - a two to three-fold increase in AUC and Cmax of asimadoline was observed with concomitant administration of ketoconazole. The most common adverse events are diarrhea, nausea, sinusitis, headache and fatigue.
CNS Activity
Originator
Approval Year
Doses
AEs
Sourcing
PubMed
Patents
Sample Use Guides
0.5 mg and placebo were administered twice daily for up to 12 weeks.
Route of Administration:
Oral
The cell lines (LLC-PK1, L-mdr1a, L-mdr1b and L-MDR1) were grown to confluent polarized monolayers on porous membrane filters, and polarized trans-epithelial transport of [14C]-asimadoline (10 μm) was determined. Asimadoline is well transported in vitro by mouse mdr1a P-gp and also by human MDR1 P-gp but not efficiently by mouse mdr1b P-gp.
