Eperisone

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofBack pain lower back••••••••••••••••••• ••••••• ••••••
Treatment ofNeck pain••••••••••••••••••• ••••••• ••••••
Treatment ofShoulder pain••••••••••••••••••• ••••••• ••••••
For therapyShoulder pain••••••••••••••••••• ••••••• ••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Eperisone is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Eperisone can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hypoglycemia can be increased when Eperisone is combined with Acarbose.
AcebutololAcebutolol may increase the arrhythmogenic activities of Eperisone.
AceclofenacThe risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Eperisone.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Eperisone hydrochlorideU38O8U7P6X56839-43-1GTAXGNCCEYZRII-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
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
  1. 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]
  2. 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]
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
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAcute Musculoskeletal Spasm Due to Low Back Pain1
3CompletedTreatmentBack Pain, Acute1
3CompletedTreatmentMuscle Spasm; Back Pain1
2CompletedTreatmentAcute Low Back Pain1
1WithdrawnTreatmentHealthy Volunteers (HV)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
Tablet, sugar coatedOral
TabletOral
Tablet, film coatedOral50 mg
Tablet, coatedOral50 mg
Tablet, sugar coatedOral50 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US3995047No1976-11-301993-03-11US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)170-172Morita, E. and Kanai,T.; U.S. Patent 3,995,047; November 30,1976; assigned to Eisai Co., Ltd. (Japan)
Predicted Properties
PropertyValueSource
Water Solubility0.0617 mg/mLALOGPS
logP4.27ALOGPS
logP4.01Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)16.5Chemaxon
pKa (Strongest Basic)8.77Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area20.31 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity80.95 m3·mol-1Chemaxon
Polarizability31.74 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Download (35.3 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001i-6920000000-2a6df63ca307725624c4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1190000000-1cac1066398349d91b9f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0960000000-a75d121f7fc27cb8a765
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-7920000000-a75d1065474a190e312c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-4970000000-497edddca326374265a6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9830000000-8022f2eb3e132ffb167c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-7960000000-8fa55ddea1baabd97d13
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-163.53036
predicted
DeepCCS 1.0 (2019)
[M+H]+165.88837
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.9815
predicted
DeepCCS 1.0 (2019)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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 December 02, 2023 07:01