Explore a selection of our essential drug information below, or:
Identification
- Summary
Eperisone is an antispasmodic that functions through voltage-gated channel blockade, notably with little to no sedation, effective in relaxing skeletal muscles and vascular smooth muscles.
- Generic Name
- Eperisone
- DrugBank Accession Number
- DB08992
- Background
Eperisone is an antispasmodic drug which relaxes both skeletal muscles and vascular smooth muscles, and demonstrates a variety of effects such as reduction of myotonia, improvement of circulation, and suppression of the pain reflex. It is not approved for use in the United States, but is available in other countries like India, South Korea, and Bangladesh.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Eperisone (DB08992)
- Weight
- Average: 259.3865
Monoisotopic: 259.193614427 - Chemical Formula
- C17H25NO
- Synonyms
- (2RS)-1-(4-ethylphenyl)-2-methyl-3-(1-piperidyl)propan-1-one
- Eperison
- Eperisona
- Epérisone
- Eperisone
- Eperisonum
- External IDs
- EMPP
Pharmacology
- Indication
Not Available
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.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Back pain lower back •••••••••••• ••••••• ••••••• •••••• Treatment of Neck pain •••••••••••• ••••••• ••••••• •••••• Treatment of Shoulder pain •••••••••••• ••••••• ••••••• •••••• For therapy Shoulder pain •••••••••••• ••••••• ••••••• •••••• - Associated Therapies
- 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
- Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Eperisone is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Eperisone can be increased when it is combined with Abametapir. Acarbose The risk or severity of hypoglycemia can be increased when Eperisone is combined with Acarbose. Acebutolol Acebutolol may increase the arrhythmogenic activities of Eperisone. Aceclofenac The risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Eperisone. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Eperisone hydrochloride U38O8U7P6X 56839-43-1 GTAXGNCCEYZRII-UHFFFAOYSA-N - International/Other Brands
- Akitonal (Choseido Pharmaceutical) / Elexin (South Korea) / Myonal (Eisai) / Myoperison (Kobayashi Kako) / Rapisone (Abbott)
Categories
- ATC Codes
- M03BX09 — Eperisone
- Drug Categories
- Agents causing hyperkalemia
- Antiarrhythmic agents
- Autonomic Agents
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Calcium-Regulating Hormones and Agents
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Ketones
- Membrane Transport Modulators
- Moderate Risk QTc-Prolonging Agents
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Musculo-Skeletal System
- Neuromuscular Agents
- Parasympatholytics
- Peripheral Nervous System Agents
- QTc Prolonging Agents
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Alkyl-phenylketones
- Alternative Parents
- Phenylpropanes / Benzoyl derivatives / Aryl alkyl ketones / Piperidines / Beta-amino ketones / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alkyl-phenylketone / Amine / Aromatic heteromonocyclic compound / Aryl alkyl ketone / Azacycle / Benzenoid / Benzoyl / Beta-aminoketone / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- piperidines, aromatic ketone (CHEBI:77070)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 2M2P0551D3
- CAS number
- 64840-90-0
- InChI Key
- SQUNAWUMZGQQJD-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H25NO/c1-3-15-7-9-16(10-8-15)17(19)14(2)13-18-11-5-4-6-12-18/h7-10,14H,3-6,11-13H2,1-2H3
- IUPAC Name
- 1-(4-ethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one
- SMILES
- CCC1=CC=C(C=C1)C(=O)C(C)CN1CCCCC1
References
- General References
- Cabitza P, Randelli P: Efficacy and safety of eperisone in patients with low back pain: a double blind randomized study. Eur Rev Med Pharmacol Sci. 2008 Jul-Aug;12(4):229-35. [Article]
- Jeoung MK, Jeong ES, Kim NH, Kim CS, Chung YB, Lee YM, Ahn SY, Cho HE, Lee YH, Hong JT, Moon DC: Determination of eperisone in human plasma by liquid chromatography-ESI-tandem mass spectrometry. Arch Pharm Res. 2007 Sep;30(9):1174-8. [Article]
- External Links
- KEGG Drug
- D01671
- PubChem Compound
- 3236
- PubChem Substance
- 310264953
- ChemSpider
- 3123
- ChEBI
- 77070
- ChEMBL
- CHEMBL1902981
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Eperisone
- MSDS
- Download (138 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Healthy Volunteers (HV) 1 somestatus stop reason just information to hide Not Available Unknown Status Treatment Back Pain Lower Back 1 somestatus stop reason just information to hide 3 Completed Treatment Acute Musculoskeletal Spasm Due to Low Back Pain 1 somestatus stop reason just information to hide 3 Completed Treatment Back Pain, Acute 1 somestatus stop reason just information to hide 3 Completed Treatment Muscle Spasm; Back Pain 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral Tablet Oral 50 MG Tablet, sugar coated Oral Tablet, film coated Oral 50 mg Tablet, coated Oral 50 mg Tablet, sugar coated Oral 50 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US3995047 No 1976-11-30 1993-03-11 US 
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 170-172 Morita, E. and Kanai,T.; U.S. Patent 3,995,047; November 30,1976; assigned to Eisai Co., Ltd. (Japan) - Predicted Properties
Property Value Source Water Solubility 0.0617 mg/mL ALOGPS logP 4.27 ALOGPS logP 4.01 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 16.5 Chemaxon pKa (Strongest Basic) 8.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 20.31 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 80.95 m3·mol-1 Chemaxon Polarizability 31.74 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Download (35.3 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-6920000000-2a6df63ca307725624c4 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-1190000000-1cac1066398349d91b9f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0960000000-a75d121f7fc27cb8a765 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-7920000000-a75d1065474a190e312c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-4970000000-497edddca326374265a6 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-9830000000-8022f2eb3e132ffb167c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a59-7960000000-8fa55ddea1baabd97d13 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 163.53036 predictedDeepCCS 1.0 (2019) [M+H]+ 165.88837 predictedDeepCCS 1.0 (2019) [M+Na]+ 171.9815 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]
Drug created at June 11, 2014 19:41 / Updated at October 07, 2024 17:57