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MedKoo Cat#: 530139 | Name: Asimadoline HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Asimadoline HCl is a κ-opioid receptor agonist potentially for the treatment of pruritus. Asimadoline has also been shown to be used in the treatment of irritable bowel syndrome.

Chemical Structure

Asimadoline HCl
Asimadoline HCl
CAS#185951-07-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 530139

Name: Asimadoline HCl

CAS#: 185951-07-9 (HCl)

Chemical Formula: C27H31ClN2O2

Exact Mass: 0.0000

Molecular Weight: 451.01

Elemental Analysis: C, 71.91; H, 6.93; Cl, 7.86; N, 6.21; O, 7.09

Price and Availability

Size Price Availability Quantity
5mg USD 300.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
153205-46-0 (free base) 185951-07-9 (HCl)
Synonym
EMD-61753; EMR-63320; ONO-3951; EMD61753; EMR63320; ONO3951; EMD 61753; EMR 63320; ONO 3951
IUPAC/Chemical Name
N-[(1S)-2-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-phenylethyl]-N-methyl-a-phenyl-benzeneacetamide hydrochloride
InChi Key
GMJSLABTEURMBF-CLSOAGJSSA-N
InChi Code
InChI=1S/C27H30N2O2.ClH/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;1H/t24-,25+;/m0./s1
SMILES Code
O=C(N([C@@H](C1=CC=CC=C1)CN2C[C@@H](O)CC2)C)C(C3=CC=CC=C3)C4=CC=CC=C4.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 451.01 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Mangel AW, Williams VS. Asimadoline in the treatment of irritable bowel syndrome. Expert Opin Investig Drugs. 2010 Oct;19(10):1257-64. doi: 10.1517/13543784.2010.515209. Review. PubMed PMID: 20809870. 2: Camilleri M. Novel pharmacology: asimadoline, a kappa-opioid agonist, and visceral sensation. Neurogastroenterol Motil. 2008 Sep;20(9):971-9. doi: 10.1111/j.1365-2982.2008.01183.x. Review. PubMed PMID: 18715494; PubMed Central PMCID: PMC2698012. 3: Mangel AW, Bornstein JD, Hamm LR, Buda J, Wang J, Irish W, Urso D. Clinical trial: asimadoline in the treatment of patients with irritable bowel syndrome. Aliment Pharmacol Ther. 2008 Jul;28(2):239-49. doi: 10.1111/j.1365-2036.2008.03730.x. PubMed PMID: 18466359. 4: Talley NJ, Choung RS, Camilleri M, Dierkhising RA, Zinsmeister AR. Asimadoline, a kappa-opioid agonist, and satiation in functional dyspepsia. Aliment Pharmacol Ther. 2008 Jun 1;27(11):1122-31. doi: 10.1111/j.1365-2036.2008.03676.x. PubMed PMID: 18331462; PubMed Central PMCID: PMC3935285. 5: Jolivalt CG, Jiang Y, Freshwater JD, Bartoszyk GD, Calcutt NA. Dynorphin A, kappa opioid receptors and the antinociceptive efficacy of asimadoline in streptozotocin-induced diabetic rats. Diabetologia. 2006 Nov;49(11):2775-85. PubMed PMID: 16924480. 6: Mangel AW, Hicks GA. Asimadoline and its potential for the treatment of diarrhea-predominant irritable bowel syndrome: a review. Clin Exp Gastroenterol. 2012;5:1-10. doi: 10.2147/CEG.S23274. PubMed PMID: 22346361; PubMed Central PMCID: PMC3278196. 7: Szarka LA, Camilleri M, Burton D, Fox JC, McKinzie S, Stanislav T, Simonson J, Sullivan N, Zinsmeister AR. Efficacy of on-demand asimadoline, a peripheral kappa-opioid agonist, in females with irritable bowel syndrome. Clin Gastroenterol Hepatol. 2007 Nov;5(11):1268-75. PubMed PMID: 17900994; PubMed Central PMCID: PMC2128734. 8: Caram-Salas NL, Reyes-García G, Bartoszyk GD, Araiza-Saldaña CI, Ambriz-Tututi M, Rocha-González HI, Arreola-Espino R, Cruz SL, Granados-Soto V. Subcutaneous, intrathecal and periaqueductal grey administration of asimadoline and ICI-204448 reduces tactile allodynia in the rat. Eur J Pharmacol. 2007 Nov 14;573(1-3):75-83. PubMed PMID: 17643411. 9: Delvaux M, Beck A, Jacob J, Bouzamondo H, Weber FT, Frexinos J. Effect of asimadoline, a kappa opioid agonist, on pain induced by colonic distension in patients with irritable bowel syndrome. Aliment Pharmacol Ther. 2004 Jul 15;20(2):237-46. PubMed PMID: 15233705. 10: Schreiber R, Bartoszyk GD, Kunzelmann K. The kappa-opioid receptor agonist asimadoline inhibits epithelial transport in mouse trachea and colon. Eur J Pharmacol. 2004 Oct 25;503(1-3):185-90. PubMed PMID: 15496313. 11: Delgado-Aros S, Chial HJ, Cremonini F, Ferber I, McKinzie S, Burton DD, Camilleri M. Effects of asimadoline, a kappa-opioid agonist, on satiation and postprandial symptoms in health. Aliment Pharmacol Ther. 2003 Sep 1;18(5):507-14. PubMed PMID: 12950423. 12: Delgado-Aros S, Chial HJ, Camilleri M, Szarka LA, Weber FT, Jacob J, Ferber I, McKinzie S, Burton DD, Zinsmeister AR. Effects of a kappa-opioid agonist, asimadoline, on satiation and GI motor and sensory functions in humans. Am J Physiol Gastrointest Liver Physiol. 2003 Apr;284(4):G558-66. PubMed PMID: 12631557. 13: Kramer HJ, Uhl W, Ladstetter B, Bäcker A. Influence of asimadoline, a new kappa-opioid receptor agonist, on tubular water absorption and vasopressin secretion in man. Br J Clin Pharmacol. 2000 Sep;50(3):227-35. PubMed PMID: 10971307; PubMed Central PMCID: PMC2014989. 14: Bush KA, Kirkham BW, Walker JS. The kappa-opioid agonist, asimadoline, alters cytokine gene expression in adjuvant arthritis. Rheumatology (Oxford). 2001 Sep;40(9):1013-21. PubMed PMID: 11561112. 15: Binder W, Walker JS. Effect of the peripherally selective kappa-opioid agonist, asimadoline, on adjuvant arthritis. Br J Pharmacol. 1998 Jun;124(4):647-54. PubMed PMID: 9690855; PubMed Central PMCID: PMC1565434. 16: Jonker JW, Wagenaar E, van Deemter L, Gottschlich R, Bender HM, Dasenbrock J, Schinkel AH. Role of blood-brain barrier P-glycoprotein in limiting brain accumulation and sedative side-effects of asimadoline, a peripherally acting analgaesic drug. Br J Pharmacol. 1999 May;127(1):43-50. PubMed PMID: 10369454; PubMed Central PMCID: PMC1565984. 17: Walker JS, Scott C, Bush KA, Kirkham BW. Effects of the peripherally selective kappa-opioid asimadoline, on substance P and CGRP mRNA expression in chronic arthritis of the rat. Neuropeptides. 2000 Jun-Aug;34(3-4):193-202. PubMed PMID: 11021980. 18: Walker J, Catheline G, Guilbaud G, Kayser V. Lack of cross-tolerance between the antinociceptive effects of systemic morphine and asimadoline, a peripherally-selective kappa-opioid agonist, in CCI-neuropathic rats. Pain. 1999 Dec;83(3):509-16. PubMed PMID: 10568859. 19: Binder W, Scott C, Walker JS. 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. PubMed PMID: 10336675. 20: Bender HM, Dasenbrock J. Brain concentrations of asimadoline in mice: the influence of coadministration of various P-glycoprotein substrates. Int J Clin Pharmacol Ther. 1998 Feb;36(2):76-9. PubMed PMID: 9520149.