Asimadoline
Identification
- Generic Name
- Asimadoline
- DrugBank Accession Number
- DB05104
- Background
Asimadoline is a proprietary small molecule therapeutic, originally discovered by Merck KGaA of Darmstadt, Germany. Asimadoline was originally developed to treat peripheral pain such as arthritis. Asimadoline is an orally administered agent that acts as a kappa opioid receptor agonist. It has shown encouraging clinical efficacy for the treatment of IBS in a barostat study in IBS patients and has the potential for treating other gastrointestinal diseases.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 414.5393
Monoisotopic: 414.230728214 - Chemical Formula
- C27H30N2O2
- Synonyms
- Asimadoline
- External IDs
- EMD 61753
Pharmacology
- Indication
Investigated for use/treatment in irritable bowel syndrome (IBS).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Asimadoline is an orally administered agent that acts as a kappa opioid receptor agonist. Kappa opioid receptors are found mostly in the digestive tract and are believed to play an important role in control of visceral pain and bowel motility. As such, kappa opioid agonists are ideal candidates to relieve the pain, discomfort an impaired motility common to IBS and other gastrointestinal disorders.
Target Actions Organism UKappa-type opioid receptor Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Phenylacetamides / Aralkylamines / N-alkylpyrrolidines / Tertiary carboxylic acid amides / Trialkylamines / Secondary alcohols / Amino acids and derivatives / 1,2-aminoalcohols / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- D0VK52NV5M
- CAS number
- 153205-46-0
- InChI Key
- JHLHNYVMZCADTC-LOSJGSFVSA-N
- 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
- IUPAC Name
- N-[(1S)-2-[(3S)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-diphenylacetamide
- SMILES
- CN([C@H](CN1CC[C@H](O)C1)C1=CC=CC=C1)C(=O)C(C1=CC=CC=C1)C1=CC=CC=C1
References
- General References
- 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. [Article]
- 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. [Article]
- 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. Epub 2007 Sep 27. [Article]
- 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. [Article]
- External Links
- PubChem Compound
- 179340
- PubChem Substance
- 175426945
- ChemSpider
- 156107
- BindingDB
- 50366356
- ChEMBL
- CHEMBL1190199
- ZINC
- ZINC000003800054
- Wikipedia
- Asimadoline
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Diarrhoea Predominant Irritable Bowel Syndrome 1 2 Completed Treatment Atopic Dermatitis / Pruritus 1 2 Completed Treatment Irritable Bowel Syndrome (IBS) 2 2 Terminated Treatment Postoperative paralytic ileus 1 1 Completed Basic Science Healthy Subjects (HS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0112 mg/mL ALOGPS logP 3.66 ALOGPS logP 3.99 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 14.85 Chemaxon pKa (Strongest Basic) 8.17 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 43.78 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 124.81 m3·mol-1 Chemaxon Polarizability 46.07 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.991 Blood Brain Barrier + 0.8327 Caco-2 permeable + 0.5588 P-glycoprotein substrate Substrate 0.7863 P-glycoprotein inhibitor I Inhibitor 0.6416 P-glycoprotein inhibitor II Non-inhibitor 0.5923 Renal organic cation transporter Inhibitor 0.6376 CYP450 2C9 substrate Non-substrate 0.669 CYP450 2D6 substrate Non-substrate 0.6546 CYP450 3A4 substrate Substrate 0.6221 CYP450 1A2 substrate Non-inhibitor 0.9447 CYP450 2C9 inhibitor Non-inhibitor 0.8552 CYP450 2D6 inhibitor Inhibitor 0.5443 CYP450 2C19 inhibitor Non-inhibitor 0.5587 CYP450 3A4 inhibitor Non-inhibitor 0.8641 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8761 Ames test Non AMES toxic 0.8548 Carcinogenicity Non-carcinogens 0.9519 Biodegradation Not ready biodegradable 0.8859 Rat acute toxicity 2.4203 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7947 hERG inhibition (predictor II) Inhibitor 0.5233
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51