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| | ASIMADOLINE Basic information |
| Product Name: | ASIMADOLINE | | Synonyms: | ASIMADOLINE;N-[(1S)-2-[(3S)-3-Hydroxy-1-pyrrolidinyl]-1-phenylethyl]-N-methyl-alpha-phenylbenzeneacetamide;EMD 61753;Asimadoline (EMD-61753;Benzeneacetamide, N-[(1S)-2-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-phenylethyl]-N-methyl-α-phenyl-;N-((S)-2-((S)-3-Hydroxypyrrolidin-1-yl)-1-phenylethyl)-N-methyl-2,2-diphenylacetamide;EMD-61753;EMD61753;EMD 61753 | | CAS: | 153205-46-0 | | MF: | C27H30N2O2 | | MW: | 414.54 | | EINECS: | | | Product Categories: | Pharmaceutical intermediate | | Mol File: | 153205-46-0.mol |  |
| | ASIMADOLINE Chemical Properties |
| Boiling point | 605.8±55.0 °C(Predicted) | | density | 1.170±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | DMSO: 103 mg/ml | | form | A crystalline solid | | pka | 14.79±0.20(Predicted) |
| | ASIMADOLINE Usage And Synthesis |
| Uses | Acimadolin is a K-opioid agonist that raises the sensitivity threshold in patients with irritable bowel syndrome (IBS), barely crosses the blood-brain barrier, and is well tolerated. It cannot significantly improve the pain threshold of patients, Can significantly reduce pain intensity. | | Biological Activity | Asimadoline (EMD-61753) is an orally active, selective, peripherally active κ-opioid agonist with IC50s of 5.6 nM and 1.2 nM for guinea pig and human recombinant κ-opioid, respectively. It has low permeability to the blood-brain barrier and has peripheral anti-inflammatory effects. Also Asimadoline improves allodynia in diabetic rats and has potential for irritable bowel syndrome (IBS) research. | | in vitro | Asimadoline (EMD-61753) has high selectively in κ: μ: δ opioid binding ratios of 1:501:498 in human recombinant receptors. The IC 50 for Asimadoline binding to μ -opioid receptors is 3 μM and to δ-opioid receptors is 0.7 μM. The IC 50 values for D1, D2, kainate, σ, PCP/NMDA, H1, α1, α2, M1/M2, glycine, 5HT1A, 5HT1C, 5HT1D, 5HT2, 5HT3, AMPA and kainate/AMPA receptors are all >10 μM.
It has affinity to sodium and L type Ca 2+ ion channels at IC 50 concentrations 150 to 800 fold the IC 50 for the κ receptors.
At high concentrations, Asimadoline demonstrates spasmolytic action against 400 μM barium chloride in the rat duodenum (IC 50 =4.2 μM), suggesting that Asimadoline may block the direct stimulant effects of barium on smooth muscle through mechanisms that are not identified.
| | in vivo | Asimadoline (EMD-61753; 1, 5, 15 mg/kg; sc) acutely ameliorates both formalin-evoked hyperalgesia and tactile allodynia in diabetic rats.
The absorption rate following oral administration is 80% in rats and >90% in dogs and monkeys. The metabolism of Asimadoline is rapid and appears similar in animals and man. Asimadoline has peripheral anti-inflammatory actions that are partly mediated through increase in joint fluid substance P levels. | | target | IC50: 5.6 nM (guinea pig κ opioid), 1.2 nM (human recombinant κ opioid) |
| | ASIMADOLINE Preparation Products And Raw materials |
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