Eperisone

Identification

Name
Eperisone
Accession Number
DB08992
Type
Small Molecule
Groups
Approved, 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
Structured Indications
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
DrugInteractionDrug group
2-HYDROXY-1,4-NAPHTHOQUINONEThe risk or severity of adverse effects can be increased when 2-HYDROXY-1,4-NAPHTHOQUINONE is combined with Eperisone.Experimental
2-mercaptobenzothiazoleThe risk or severity of adverse effects can be increased when 2-mercaptobenzothiazole is combined with Eperisone.Vet Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Eperisone.Approved, Investigational
AmobarbitalThe metabolism of Eperisone can be increased when combined with Amobarbital.Approved, Illicit
AmorolfineThe risk or severity of adverse effects can be increased when Amorolfine is combined with Eperisone.Approved, Investigational
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Eperisone.Approved, Investigational
AnidulafunginThe risk or severity of adverse effects can be increased when Anidulafungin is combined with Eperisone.Approved, Investigational
ArotinololThe risk or severity of hypotension, conduction block, and bradycardia can be increased when Arotinolol is combined with Eperisone.Investigational
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Eperisone.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Eperisone is combined with Atorvastatin.Approved
AtosibanThe risk or severity of adverse effects can be increased when Eperisone is combined with Atosiban.Approved, Investigational
Bafilomycin A1The risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Eperisone.Experimental
BarbexacloneThe metabolism of Eperisone can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Eperisone can be increased when combined with Barbital.Illicit
Benzoic AcidThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Eperisone.Approved
BifonazoleThe risk or severity of adverse effects can be increased when Bifonazole is combined with Eperisone.Approved, Investigational
Brefeldin AThe risk or severity of adverse effects can be increased when Brefeldin A is combined with Eperisone.Experimental
BucindololBucindolol may increase the hypotensive activities of Eperisone.Investigational
BunazosinBunazosin may increase the hypotensive activities of Eperisone.Investigational
ButenafineThe risk or severity of adverse effects can be increased when Butenafine is combined with Eperisone.Approved
ButoconazoleThe risk or severity of adverse effects can be increased when Butoconazole is combined with Eperisone.Approved
Calcium AcetateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium Acetate.Approved
Calcium CarbonateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium Carbonate.Approved
Calcium ChlorideThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium Chloride.Approved
Calcium CitrateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium Citrate.Approved
Calcium glubionateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium glubionate.Approved
Calcium GluceptateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium Gluceptate.Approved
Calcium gluconateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium gluconate.Approved, Vet Approved
Calcium lactateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium lactate.Approved, Experimental, Investigational, Vet Approved
Calcium lactate gluconateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium lactate gluconate.Experimental
Calcium levulinateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium laevulate.Experimental
Calcium pangamateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium pangamate.Experimental
Calcium PhosphateThe therapeutic efficacy of Eperisone can be decreased when used in combination with Calcium Phosphate.Approved
CandicidinThe risk or severity of adverse effects can be increased when Candicidin is combined with Eperisone.Withdrawn
Capric acidThe risk or severity of adverse effects can be increased when Capric acid is combined with Eperisone.Experimental
CarbomycinThe metabolism of Eperisone can be decreased when combined with Carbomycin.Vet Approved
CarvedilolCarvedilol may increase the hypotensive activities of Eperisone.Approved, Investigational
CaseinThe therapeutic efficacy of Eperisone can be decreased when used in combination with Casein.Approved
CaspofunginThe risk or severity of adverse effects can be increased when Caspofungin is combined with Eperisone.Approved
CerivastatinThe risk or severity of adverse effects can be increased when Eperisone is combined with Cerivastatin.Withdrawn
CeruleninThe risk or severity of adverse effects can be increased when Cerulenin is combined with Eperisone.Approved
ChloroxineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Eperisone.Approved
CiclopiroxThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Eperisone.Approved, Investigational
CimetidineThe serum concentration of Eperisone can be increased when it is combined with Cimetidine.Approved
ClarithromycinThe metabolism of Eperisone can be decreased when combined with Clarithromycin.Approved
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Eperisone.Approved
ClotrimazoleThe risk or severity of adverse effects can be increased when Clotrimazole is combined with Eperisone.Approved, Vet Approved
CordycepinThe risk or severity of adverse effects can be increased when Cordycepin is combined with Eperisone.Investigational
CyclosporineThe risk or severity of adverse effects can be increased when Cyclosporine is combined with Eperisone.Approved, Investigational, Vet Approved
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Eperisone.Investigational
DichloropheneThe risk or severity of adverse effects can be increased when Dichlorophene is combined with Eperisone.Vet Approved
DoxazosinDoxazosin may increase the hypotensive activities of Eperisone.Approved
DoxofyllineThe serum concentration of Doxofylline can be decreased when it is combined with Eperisone.Approved, Investigational
EconazoleThe risk or severity of adverse effects can be increased when Econazole is combined with Eperisone.Approved
EfavirenzThe serum concentration of Eperisone can be decreased when it is combined with Efavirenz.Approved, Investigational
EfinaconazoleThe risk or severity of adverse effects can be increased when Efinaconazole is combined with Eperisone.Approved
ErythromycinThe metabolism of Eperisone can be decreased when combined with Erythromycin.Approved, Vet Approved
FenticonazoleThe risk or severity of adverse effects can be increased when Fenticonazole is combined with Eperisone.Experimental
FluconazoleThe serum concentration of Eperisone can be increased when it is combined with Fluconazole.Approved
FlucytosineThe risk or severity of adverse effects can be increased when Flucytosine is combined with Eperisone.Approved
FlutrimazoleThe risk or severity of adverse effects can be increased when Flutrimazole is combined with Eperisone.Experimental
FluvastatinThe risk or severity of adverse effects can be increased when Eperisone is combined with Fluvastatin.Approved
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Eperisone.Approved
GlyphosateThe risk or severity of adverse effects can be increased when Glyphosate is combined with Eperisone.Experimental
GriseofulvinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Eperisone.Approved, Vet Approved
HachimycinThe risk or severity of adverse effects can be increased when Hachimycin is combined with Eperisone.Experimental
HaloproginThe risk or severity of adverse effects can be increased when Haloprogin is combined with Eperisone.Approved, Withdrawn
HexetidineThe risk or severity of adverse effects can be increased when Hexetidine is combined with Eperisone.Approved, Investigational
HexobarbitalThe metabolism of Eperisone can be increased when combined with Hexobarbital.Approved
IndoraminIndoramin may increase the hypotensive activities of Eperisone.Withdrawn
IsoconazoleThe risk or severity of adverse effects can be increased when Isoconazole is combined with Eperisone.Approved
ItraconazoleThe risk or severity of adverse effects can be increased when Itraconazole is combined with Eperisone.Approved, Investigational
JosamycinThe metabolism of Eperisone can be decreased when combined with Josamycin.Approved, Investigational
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Eperisone.Approved, Investigational
KitasamycinThe metabolism of Eperisone can be decreased when combined with Kitasamycin.Experimental
LabetalolLabetalol may increase the hypotensive activities of Eperisone.Approved
LorpiprazoleThe therapeutic efficacy of Eperisone can be increased when used in combination with Lorpiprazole.Approved
LovastatinThe risk or severity of adverse effects can be increased when Eperisone is combined with Lovastatin.Approved, Investigational
MefloquineThe therapeutic efficacy of Eperisone can be decreased when used in combination with Mefloquine.Approved
MepartricinThe risk or severity of adverse effects can be increased when Mepartricin is combined with Eperisone.Experimental
MethocarbamolThe risk or severity of adverse effects can be increased when Eperisone is combined with Methocarbamol.Approved, Vet Approved
MethohexitalThe metabolism of Eperisone can be increased when combined with Methohexital.Approved
MethylphenobarbitalThe metabolism of Eperisone can be increased when combined with Methylphenobarbital.Approved
MevastatinThe risk or severity of adverse effects can be increased when Mevastatin is combined with Eperisone.Experimental
MianserinThe therapeutic efficacy of Eperisone can be decreased when used in combination with Mianserin.Approved, Investigational
MicafunginThe risk or severity of adverse effects can be increased when Micafungin is combined with Eperisone.Approved, Investigational
MiconazoleThe risk or severity of adverse effects can be increased when Miconazole is combined with Eperisone.Approved, Investigational, Vet Approved
MiltefosineThe risk or severity of adverse effects can be increased when Miltefosine is combined with Eperisone.Approved
MonensinThe risk or severity of adverse effects can be increased when Monensin is combined with Eperisone.Vet Approved
MyxothiazolThe risk or severity of adverse effects can be increased when Myxothiazol is combined with Eperisone.Experimental
NafcillinThe metabolism of Eperisone can be increased when combined with Nafcillin.Approved
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Eperisone.Approved
NatamycinThe risk or severity of adverse effects can be increased when Natamycin is combined with Eperisone.Approved
NifuratelThe risk or severity of adverse effects can be increased when Nifuratel is combined with Eperisone.Experimental
Nikkomycin ZThe risk or severity of adverse effects can be increased when Nikkomycin Z is combined with Eperisone.Investigational
NitroprussideEperisone may increase the hypotensive activities of Nitroprusside.Approved
NitroxolineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Eperisone.Approved
NystatinThe risk or severity of adverse effects can be increased when Nystatin is combined with Eperisone.Approved, Vet Approved
OleandomycinThe metabolism of Eperisone can be decreased when combined with Oleandomycin.Vet Approved
OmoconazoleThe risk or severity of adverse effects can be increased when Omoconazole is combined with Eperisone.Experimental
OrlistatThe serum concentration of Eperisone can be decreased when it is combined with Orlistat.Approved, Investigational
OxiconazoleThe risk or severity of adverse effects can be increased when Oxiconazole is combined with Eperisone.Approved
PafuramidineThe risk or severity of adverse effects can be increased when Pafuramidine is combined with Eperisone.Investigational
PentamidineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Eperisone.Approved
PentobarbitalThe metabolism of Eperisone can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Eperisone can be increased when combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Eperisone.Approved, Vet Approved
PitavastatinThe risk or severity of adverse effects can be increased when Eperisone is combined with Pitavastatin.Approved
PosaconazoleThe risk or severity of adverse effects can be increased when Posaconazole is combined with Eperisone.Approved, Investigational, Vet Approved
PravastatinThe risk or severity of adverse effects can be increased when Eperisone is combined with Pravastatin.Approved
PrazosinPrazosin may increase the hypotensive activities of Eperisone.Approved
PregabalinThe therapeutic efficacy of Eperisone can be decreased when used in combination with Pregabalin.Approved, Illicit, Investigational
PrimidoneThe metabolism of Eperisone can be increased when combined with Primidone.Approved, Vet Approved
PyrrolnitrinThe risk or severity of adverse effects can be increased when Pyrrolnitrin is combined with Eperisone.Experimental
RadicicolThe risk or severity of adverse effects can be increased when Radicicol is combined with Eperisone.Experimental
RifabutinThe serum concentration of Eperisone can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Eperisone can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Eperisone can be decreased when it is combined with Rifapentine.Approved
RifaximinThe serum concentration of Eperisone can be decreased when it is combined with Rifaximin.Approved, Investigational
RosuvastatinThe risk or severity of adverse effects can be increased when Eperisone is combined with Rosuvastatin.Approved
Salicylhydroxamic AcidThe risk or severity of adverse effects can be increased when Salicylhydroxamic Acid is combined with Eperisone.Experimental
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Eperisone.Approved, Vet Approved
SecobarbitalThe metabolism of Eperisone can be increased when combined with Secobarbital.Approved, Vet Approved
SertaconazoleThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Eperisone.Approved
SilodosinSilodosin may increase the hypotensive activities of Eperisone.Approved
SimvastatinThe risk or severity of adverse effects can be increased when Eperisone is combined with Simvastatin.Approved
SinefunginThe risk or severity of adverse effects can be increased when Sinefungin is combined with Eperisone.Experimental
SirolimusThe risk or severity of adverse effects can be increased when Sirolimus is combined with Eperisone.Approved, Investigational
SolithromycinThe metabolism of Eperisone can be decreased when combined with Solithromycin.Investigational
SulconazoleThe risk or severity of adverse effects can be increased when Sulconazole is combined with Eperisone.Approved
TamsulosinTamsulosin may increase the hypotensive activities of Eperisone.Approved, Investigational
TavaboroleThe risk or severity of adverse effects can be increased when Tavaborole is combined with Eperisone.Approved
TelithromycinThe metabolism of Eperisone can be decreased when combined with Telithromycin.Approved
TerazosinTerazosin may increase the hypotensive activities of Eperisone.Approved
TerbinafineThe risk or severity of adverse effects can be increased when Terbinafine is combined with Eperisone.Approved, Investigational, Vet Approved
TerconazoleThe risk or severity of adverse effects can be increased when Terconazole is combined with Eperisone.Approved
ThiamylalThe metabolism of Eperisone can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Eperisone can be increased when combined with Thiopental.Approved, Vet Approved
ThymolThe risk or severity of adverse effects can be increased when Thymol is combined with Eperisone.Approved
TioconazoleThe risk or severity of adverse effects can be increased when Tioconazole is combined with Eperisone.Approved
TolciclateThe risk or severity of adverse effects can be increased when Tolciclate is combined with Eperisone.Experimental
TolnaftateThe risk or severity of adverse effects can be increased when Tolnaftate is combined with Eperisone.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Eperisone.Experimental
TrimetrexateThe risk or severity of adverse effects can be increased when Trimetrexate is combined with Eperisone.Approved, Investigational
TylosinThe metabolism of Eperisone can be decreased when combined with Tylosin.Vet Approved
UbidecarenoneThe risk or severity of adverse effects can be increased when Eperisone is combined with Ubidecarenone.Approved, Investigational, Nutraceutical
UrapidilUrapidil may increase the hypotensive activities of Eperisone.Investigational
VoriconazoleThe risk or severity of adverse effects can be increased when Voriconazole is combined with Eperisone.Approved, Investigational
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
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)

Drug created on June 11, 2014 13:41 / Updated on December 01, 2017 17:20