EPERISONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H25NO
Molecular Weight	259.3865
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=CC=C(C=C1)C(=O)C(C)CN2CCCCC2

InChI

InChIKey=SQUNAWUMZGQQJD-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H25NO
Molecular Weight	259.3865
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/22120855
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/18836866

Eperisone is an antispasmodic drug approved in Japan for the treatment of of diseases characterized by muscle stiffness and pain. It is believed that eperisone exerts its effect through inhibition of sodium channels. The drug is still being marketed in Asia under the name Myonal (Square Pharmaceuticals).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
skeletal muscle contraction 3 Target ID: GO:0003009 Sources: http://www.eisai.jp/medical/products/di/EPI/MYO_T-G_EPI.pdf	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Low back pain 22 Sources: http://www.eisai.jp/medical/products/di/EPI/MYO_T-G_EPI.pdf	Palliative	Approved 8583	MYONAL Approved Use Improvement of myotonic conditions caused by Neck-shoulder-arm syndrome, scapulohumeral periarthritis and low back pain; Spastic paralysis caused by the following diseases: Cerebrovascular disorders, spastic spinal paralysis, cervical spondylosis, post-surgical sequelae (including cerebrospinal tumor), sequelae of trauma (spinal injury and head injury), amyotrophic lateral sclerosis, infantile cerebral palsy, spinocerebellar degeneration, spinal vascular disorders, subacute myelo-optico neuropathy (SMON) and other encephalomyelopathies.
Spastic paralysis 3 Sources: http://www.eisai.jp/medical/products/di/EPI/MYO_T-G_EPI.pdf	Palliative	Approved 8583	MYONAL Approved Use Improvement of myotonic conditions caused by Neck-shoulder-arm syndrome, scapulohumeral periarthritis and low back pain; Spastic paralysis caused by the following diseases: Cerebrovascular disorders, spastic spinal paralysis, cervical spondylosis, post-surgical sequelae (including cerebrospinal tumor), sequelae of trauma (spinal injury and head injury), amyotrophic lateral sclerosis, infantile cerebral palsy, spinocerebellar degeneration, spinal vascular disorders, subacute myelo-optico neuropathy (SMON) and other encephalomyelopathies.
Neck-shoulder-arm syndrome 2 Sources: http://www.eisai.jp/medical/products/di/EPI/MYO_T-G_EPI.pdf	Palliative	Approved 8583	MYONAL Approved Use Improvement of myotonic conditions caused by Neck-shoulder-arm syndrome, scapulohumeral periarthritis and low back pain; Spastic paralysis caused by the following diseases: Cerebrovascular disorders, spastic spinal paralysis, cervical spondylosis, post-surgical sequelae (including cerebrospinal tumor), sequelae of trauma (spinal injury and head injury), amyotrophic lateral sclerosis, infantile cerebral palsy, spinocerebellar degeneration, spinal vascular disorders, subacute myelo-optico neuropathy (SMON) and other encephalomyelopathies.
Scapulohumeral periarthritis 3 Sources: http://www.eisai.jp/medical/products/di/EPI/MYO_T-G_EPI.pdf	Palliative	Approved 8583	MYONAL Approved Use Improvement of myotonic conditions caused by Neck-shoulder-arm syndrome, scapulohumeral periarthritis and low back pain; Spastic paralysis caused by the following diseases: Cerebrovascular disorders, spastic spinal paralysis, cervical spondylosis, post-surgical sequelae (including cerebrospinal tumor), sequelae of trauma (spinal injury and head injury), amyotrophic lateral sclerosis, infantile cerebral palsy, spinocerebellar degeneration, spinal vascular disorders, subacute myelo-optico neuropathy (SMON) and other encephalomyelopathies.

C_max

Value	Dose	Analyte	Population
7.5 ng/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.8 ng/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.9 ng/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2 ng/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.21 ng/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.18 ng/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.65 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32024955/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.46 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32024955/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
19.68 ng × h/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
20.29 ng × h/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
21.08 ng × h/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.86 ng × h/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
13.2 ng × h/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
20.27 ng × h/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
20.88 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32024955/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
22.91 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32024955/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
1.6 h OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.68 h OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.75 h OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=24	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.37 h OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.55 h OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.93 h OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/470007_1249009F1473_1_V09_1F.pdf#page=20	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.81 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32024955/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.99 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32024955/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
4.2% OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/170033_1249009D1030_1_008_1F.pdf#page=25			EPERISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 3 times / day multiple, oral Higher than recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19458926/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19458926/	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (grade 3, 2.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/19458926/

AEs

AE	Significance	Dose	Population
Headache	grade 3, 2.5% Disc. AE	100 mg 3 times / day multiple, oral Higher than recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19458926/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19458926/

PubMed

Title	Date	PubMed
Efficacy and safety of eperisone in patients with low back pain: a double blind randomized study.	2008-08-30	18727454
Determination of eperisone in human plasma by liquid chromatography-ESI-tandem mass spectrometry.	2007-09	17958338

Patents

Sample Use Guides

In Vivo Use Guide

150 mg of eperisone hydrochloride daily in three divided doses after meals

Route of Administration: Oral

In Vitro Use Guide

Eperisone (25–200 uM) depressed the ventral root potential of isolated hemisected spinal cord of 6-day-old rats.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:11 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:11 GMT 2025`
Record UNII	2M2P0551D3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPERISONE

Official Name

English

EPERISONE [JAN]

Preferred Name

English

Eperisone [WHO-DD]

Common Name

English

EPERISONE [MI]

Common Name

English

1-(4-ETHYLPHENYL)-2-METHYL-3-(1-PIPERIDINYL)-1-PROPANONE

Systematic Name

English

eperisone [INN]

Common Name

English

4'-ETHYL-2-METHYL-3-PIPERIDINOPROPIOPHENONE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

M03BX09