U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H23NO.ClH
Molecular Weight 281.821
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOLPERISONE HYDROCHLORIDE

SMILES

Cl.CC(CN1CCCCC1)C(=O)C2=CC=C(C)C=C2

InChI

InChIKey=ZBUVYROEHQQAKL-UHFFFAOYSA-N
InChI=1S/C16H23NO.ClH/c1-13-6-8-15(9-7-13)16(18)14(2)12-17-10-4-3-5-11-17;/h6-9,14H,3-5,10-12H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula C16H23NO
Molecular Weight 245.3599
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://pharmacybook.net/mydocalm/ | http://en.remedy-info.com/ovr0_midokalm.html | https://www.ncbi.nlm.nih.gov/pubmed/18482024 | https://www.ncbi.nlm.nih.gov/pubmed/232053

Tolperisone is a centrally acting muscle relaxant first synthesized in 1956 and used in clinical practice since the 1960’s. Tolperisone is an aryl alkyl β-aminoketone with an asymmetric carbon atom α to the carbonyl group. The dextrorotatory enantiomer was reported less effective, however, no detailed analyses of the enantiomers are available. The precise mechanism of action of tolperisone is not fully known. The most prominent effect of tolperisone is its inhibitory action on pathways of spinal reflexes. It suppresses the mono and polysynaptic reflex transmission by both pre-synaptic and post-synaptic mechanisms.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
198.0 µM [IC50]
1062.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Mydocalm

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
297.6 ng/mL
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
64.1 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
90.88 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
229.47 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
54 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
98.85 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
205.2 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
70.89 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
115.44 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
516 ng × h/mL
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
111.2 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
151.92 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
682.03 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
81.09 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
170.2 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
274.6 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
101.11 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
194.63 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.14 h
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3.3 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.7 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.66 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.91 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.33 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.82 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.84 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.44 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOLPERISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
900 mg 3 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 3 times / day
Route: oral
Route: multiple
Dose: 900 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Other AEs: Apnoea, Myoclonus...
Other AEs:
Apnoea
Myoclonus
Tachycardia
Hypotension
Sources:
25 mg single, oral
Studied dose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: Urticaria, Anxiety...
Other AEs:
Urticaria
Anxiety
Sources:
2700 mg single, oral
Accidental dose
Dose: 2700 mg
Route: oral
Route: single
Dose: 2700 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
Other AEs: Seizures, Apnoea...
Other AEs:
Seizures
Apnoea
Cardiac arrest
Acidosis (grade 3)
Hypokalaemia
Brain hypoxia
Sources:
AEs

AEs

AESignificanceDosePopulation
Apnoea
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Hypotension
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Myoclonus
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Tachycardia
15000 mg single, oral
Overdose
Dose: 15000 mg
Route: oral
Route: single
Dose: 15000 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Anxiety
25 mg single, oral
Studied dose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Urticaria
25 mg single, oral
Studied dose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Apnoea
2700 mg single, oral
Accidental dose
Dose: 2700 mg
Route: oral
Route: single
Dose: 2700 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
Brain hypoxia
2700 mg single, oral
Accidental dose
Dose: 2700 mg
Route: oral
Route: single
Dose: 2700 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
Cardiac arrest
2700 mg single, oral
Accidental dose
Dose: 2700 mg
Route: oral
Route: single
Dose: 2700 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
Hypokalaemia
2700 mg single, oral
Accidental dose
Dose: 2700 mg
Route: oral
Route: single
Dose: 2700 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
Seizures
2700 mg single, oral
Accidental dose
Dose: 2700 mg
Route: oral
Route: single
Dose: 2700 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
Acidosis grade 3
2700 mg single, oral
Accidental dose
Dose: 2700 mg
Route: oral
Route: single
Dose: 2700 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Comparative study of therapeutic response to baclofen vs tolperisone in spasticity.
2017-03
Pharmacological interventions other than botulinum toxin for spasticity after stroke.
2016-10-06
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011-07-14
Differential effects of painful and non-painful stimulation on tactile processing in fibromyalgia syndrome and subjects with masochistic behaviour.
2010-12-28
Classification of drugs based on properties of sodium channel inhibition: a comparative automated patch-clamp study.
2010-12-20
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010-12
[IGOST guideline for pharmacotherapy of low back pain].
2010-08-12
Tolperisone.
2010-02
NMR analysis, protonation equilibria and decomposition kinetics of tolperisone.
2009-12-05
[Co-analgesics--today and tomorrow--a receptor-based overview of therapeutical options].
2009-11
[New therapies for spastic movement disorders].
2009-10
[Efficiency local injection therapy with preparation mydocalm in myofascial pain syndrome cervicobrachial region].
2009
Cannabinoids in the management of spasticity associated with multiple sclerosis.
2008-10
[Comparative efficacy of different muscle relaxants in the rehabilitation of post-stroke patients with spasticity].
2008
Tolperisone: a typical representative of a class of centrally acting muscle relaxants with less sedative side effects.
2008
Determination of eperisone in human plasma by liquid chromatography-ESI-tandem mass spectrometry.
2007-09
Considerable interindividual variation in the pharmacokinetics of tolperisone HCl.
2007-02
Silperisone: a centrally acting muscle relaxant.
2007-01-18
Grand rounds: an outbreak of toxic hepatitis among industrial waste disposal workers.
2007-01
[Use of local injections of tolperisone (midocalm) in combination with tractional therapy in the treatment of vertebral static syndrome].
2007
[Post-operative pain therapy of a chronic pain patient].
2006-11
[Comparative effciency of bakloferon and tolperizon central muscle relaxants in complex therapy of back pain].
2006-09
A comparative study of the action of tolperisone on seven different voltage dependent sodium channel isoforms.
2006-05-24
HPLC determination of tolperisone in human plasma.
2006-04
[A randomized, double blind, placebo-controlled study of the efficacy and safety of tolperisone in spasticity following cerebral stroke].
2006
Tolperisone-type drugs inhibit spinal reflexes via blockade of voltage-gated sodium and calcium channels.
2005-12
A randomized, double-blind, placebo-controlled study of the efficacy and safety of tolperisone in spasticity following cerebral stroke.
2005-06
[A study of mydocalm efficiency in the treatment of chronic headache of tension].
2005
[Midocalm in complex therapy of chronic low back pain syndrome].
2005
Efficacy of repeated intrathecal triamcinolone acetonide application in progressive multiple sclerosis patients with spinal symptoms.
2004-11-07
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs.
2004-10-18
Antinociceptive effects of sodium channel-blocking agents on acute pain in mice.
2004-06
[Restorative treatment of degenerative-dystrophic diseases of large joints].
2004
Separation of basic drug enantiomers by capillary electrophoresis using chicken alpha1-acid glycoprotein: insight into chiral recognition mechanism.
2003-08
Anaphylactic reactions to tolperisone (Mydocalm).
2003-06-28
[Back aches often become a chronic problem. Sodium channel block against chronification].
2003-06-19
[Fibromyalgia also has psychological origins. "Often harmony seeking perfectionists"].
2003-05-01
Identification of metabolic pathways involved in the biotransformation of tolperisone by human microsomal enzymes.
2003-05
Simultaneous micellar LC determination of lidocaine and tolperisone.
2003-03-26
[To make easier everyday life of stroke patients. Muscle relaxants diminish spasms].
2003-02-27
[Mydocalm causing anaphylaxis].
2003
Effect of muscle relaxants on experimental jaw-muscle pain and jaw-stretch reflexes: a double-blind and placebo-controlled trial.
2003
Prophylactic tolperisone for post-exercise muscle soreness causes reduced isometric force--a double-blind randomized crossover control study.
2003
[Spinal pain and its treatment with midocalm].
2003
[Patient with chronic backache. Disabled or muscle spasm patient?].
2002-12-05
[Muscular pain and fatigue: is fibromyalgia sticking behind? These points bring it to light].
2002-10-31
Protein domain of chicken alpha(1)-acid glycoprotein is responsible for chiral recognition.
2002-07-19
[Preventing chronification. So pain isn't branded into memory].
2002-05-16
[Mydeton: a centrally acting muscle relaxant drug from Gedeon Richter LTD].
2002
[Neuropharmacological studies on tolperisone hydrochloride (author's transl)].
1979-10
Patents

Sample Use Guides

In Vivo Use Guide
The usual dose is Mydocalm (tolperisone) 150 mg, 1-3 times a day. It should be taken after meal. The maximum daily dose is 450 mg
Route of Administration: Oral
The sodium channel blocking effects of Tolperisone was characterized in electrophysiological experiments on dorsal root ganglion (DRG) cells. DRG cells were acutely dissociated from rat DRG of 6-day-old male rats. Tolperisone (0, 40, 80, 160, 320, and 640 mkM) dissolved in the extracellular solution were applied onto the cells via multibarreled ejection pipettes controlled by electromagnetic valves. Currents were recorded from fast-kinetics tetrodotoxin-sensitive DRG cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:32:56 GMT 2025
Edited
by admin
on Mon Mar 31 17:32:56 GMT 2025
Record UNII
8Z075K2TIG
Record Status Validated (UNII)
Record Version
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Name Type Language
ABBSA
Preferred Name English
TOLPERISONE HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
TOLPERISONE HYDROCHLORIDE [MI]
Common Name English
MIDOCALM
Brand Name English
1-PROPANONE, 2-METHYL-1-(4-METHYLPHENYL)-3-(1-PIPERIDINYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
MINACALM
Brand Name English
ARANTOICK
Brand Name English
2,4'-DIMETHYL-3-PIPERIDINOPROPIOPHENONE HYDROCHLORIDE
Systematic Name English
NAISMERITIN
Brand Name English
TOLFREE
Brand Name English
TOLPERISONE HYDROCHLORIDE [MART.]
Common Name English
BIOCALM
Brand Name English
BESNOLINE
Brand Name English
KINEORL
Brand Name English
ISOCALM
Brand Name English
Tolperisone hydrochloride [WHO-DD]
Common Name English
TOLPERISONE HCL
Common Name English
N-553
Code English
ATMOSGEN
Brand Name English
TOLPIDOL
Brand Name English
METOSOMIN
Brand Name English
MUSCALM
Brand Name English
MENOPATOL
Brand Name English
2-METHYL-3-PIPERIDINO-1-P-TOLYLPROPAN-1-ONE HYDROCHLORIDE
Common Name English
TOLPERISONE HYDROCHLORIDE [JAN]
Common Name English
1-PIPERIDINO-2-METHYL-3-(P-TOLYL)-3-PROPANONE HYDROCHLORIDE
Common Name English
MYDOCALM
Brand Name English
TOLISARTINE
Brand Name English
2-METHYL-1-(4-METHYLPHENYL)-3-(1-PIPERIDINYL)-1-PROPANONE HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
Code System Code Type Description
CAS
3644-61-9
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
SMS_ID
100000084637
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
EVMPD
SUB04912MIG
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
ECHA (EC/EINECS)
222-876-5
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
NCI_THESAURUS
C84220
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
FDA UNII
8Z075K2TIG
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
PUBCHEM
92965
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
EPA CompTox
DTXSID2045868
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PRIMARY
DRUG BANK
DBSALT002004
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
MERCK INDEX
m10951
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1076211
Created by admin on Mon Mar 31 17:32:56 GMT 2025 , Edited by admin on Mon Mar 31 17:32:56 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY