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Asimadoline

Names

[ CAS No. ]:
153205-46-0

[ Name ]:
Asimadoline

[Synonym ]:
N-((1S)-2-((3S)-3-hydroxy-1-pyrrolidinyl)-1-phenylethyl)-N-methyl-2,2-diphenylacetamide
UNII-D0VK52NV5M
Asimadoline
Benzeneacetamide, N-((1S)-2-((3S)-3-hydroxy-1-pyrrolidinyl)-1-phenylethyl)-N-methyl-α-phenyl-
Benzeneacetamide, N-[(1S)-2-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-phenylethyl]-N-methyl-α-phenyl-
N-((aS)-a-(((3S)-3-Hydroxy-1-pyrrolidinyl)methyl)benzyl)-N-methyl-2,2-diphenylacetamide
N-{(1S)-2-[(3S)-3-Hydroxy-1-pyrrolidinyl]-1-phenylethyl}-N-methyl-2,2-diphenylacetamide

Biological Activity

[Description]:

Asimadoline is a potent κ opioid receptor agonist with IC50s of 5.6 and 1.2 nM for guinea pig and human recombinant κ opioid receptor, respectively.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Opioid Receptor
Signaling Pathways >> Neuronal Signaling >> Opioid Receptor
Research Areas >> Inflammation/Immunology

[Target]

IC50: 5.6 nM (guinea pig κ opioid), 1.2 nM (human recombinant κ opioid)[1]


[In Vitro]

The IC50 for Asimadoline binding to μ-opioid receptors is 3 µM and to δ-opioid receptors is 0.7 µM. The IC50 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 IC50, suggesting no relevant antihistaminergic, antiserotonergic or anticholinergic effects. At high concentrations, Asimadoline demonstrates spasmolytic action against 400 µM barium chloride in the rat duodenum (IC50=4.2 µM), suggesting that Asimadoline may block the direct stimulant effects of barium on smooth muscle through mechanisms that are not identified[1].

[In Vivo]

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[1]. Treatment with Asimadoline (5 mg/kg/day i.p.) produces marked (and sustained) attenuation of the disease with all three time regimes[2].

[Animal admin]

Rats: Asimadoline (5 mg/kg/day, n=10 per group) or vehicle (2 mL/kg/day, n=10) is administered to DA rats by i.p. injection twice daily (i) during the primary inflammatory phase (days 1–3); (ii) once the disease is established (days 13–21); or (iii) throughout the entire time course (days 1-21). Non-arthritic control animals receive Asimadoline (5 mg/kg/day, n=5) or vehicle (2 mL/kg/day, n=5) by i.p. injection twice daily. In all cases, disease parameters are assessed. In this experiment, the SP content of joint tissue is assessed only after the rats are killed (day 21)[2].

[References]

[1]. Camilleri M, et al. Asimadoline, a κ-Opioid Agonist, and Visceral Sensation. Neurogastroenterol Motil. 2008 Sep; 20(9): 971–979.

[2]. Binder W, et al. Involvement of substance P in the anti-inflammatory effects of the peripherally selective kappa-opioid asimadoline and the NK1 antagonist GR205171. Eur J Neurosci. 1999 Jun;11(6):2065-72.


[Related Small Molecules]

PZM-21 | Loperamide hydrochloride | Oliceridine hydrochloride | ADL5859 HCl | JDTic (dihydrochloride) | Naltrindole hydrochloride | LY-2456302 | JTC-801 | Matrine | Met-Enkephalin acetate salt | Cebranopadol | Leu-Enkephalin | DAMGO | Sinomenine HCl | SR17018

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
605.8±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C27H30N2O2

[ Molecular Weight ]:
414.539

[ Flash Point ]:
320.2±31.5 °C

[ Exact Mass ]:
414.230713

[ PSA ]:
43.78000

[ LogP ]:
3.71

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.617

[ Storage condition ]:
-20℃

Related Compounds