Identification

Name
Eperisone
Accession Number
DB08992
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
  • (2RS)-1-(4-ethylphenyl)-2-methyl-3-(1-piperidyl)propan-1-one
  • Eperison
  • Eperisona
  • Epérisone
  • Eperisonum
External IDs
EMPP
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
UNII
2M2P0551D3
CAS number
64840-90-0
Weight
Average: 259.3865
Monoisotopic: 259.193614427
Chemical Formula
C17H25NO
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Eperisone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Eperisone.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Eperisone.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Eperisone.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Eperisone is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Eperisone.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Eperisone.
AbafunginThe therapeutic efficacy of Abafungin can be increased when used in combination with Eperisone.
AcepromazineThe risk or severity of hypotension can be increased when Acepromazine is combined with Eperisone.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Eperisone.
Food Interactions
Not Available

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. [PubMed:18727454]
  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. [PubMed:17958338]
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
ATC Codes
M03BX09 — Eperisone
MSDS
Download (138 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAcute Low Back Pain1
3CompletedTreatmentAcute Low Back Pain1
3CompletedTreatmentAcute Musculoskeletal Spasm Due to Low Back Pain1
3CompletedTreatmentMuscle Spasm; Back Pain1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableRecruitingTreatmentLow Back Pain (LBP)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US3995047No1973-12-141993-03-11Us

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)16.34ChemAxon
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Phenylpropane / Benzoyl / Aryl alkyl ketone / Monocyclic benzene moiety / Beta-aminoketone / Piperidine / Benzenoid / Tertiary amine / Tertiary aliphatic amine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, aromatic ketone (CHEBI:77070)

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:22039822]

Drug created on June 11, 2014 13:41 / Updated on October 01, 2018 16:33