TOLPERISONE HYDROCHLORIDE

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 Search

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

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Tolperisone_31/WC500141050.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16126840	Inhibitor 8297		198.0 µM [IC50]
Voltage-gated calcium channel 37 Target ID: CHEMBL2363032 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16126840	Inhibitor 8297		1062.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Muscle hypertonia 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18482024	Primary		Approved 8429	Mydocalm Approved Use Unknown

PubMed

Title	Date	PubMed
Tolperisone--a novel modulator of ionic currents in myelinated axons.	2001 Dec	11989651
[Spastic syndrome. More mobile again after stroke].	2001 Mar 8	11268740
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs.	2005 Sep-Oct	16125625
Silperisone: a centrally acting muscle relaxant.	2006 Fall-Winter	17227288
A comparative study of the action of tolperisone on seven different voltage dependent sodium channel isoforms.	2006 May 24	16650844
Considerable interindividual variation in the pharmacokinetics of tolperisone HCl.	2007 Feb	17323790
Grand rounds: an outbreak of toxic hepatitis among industrial waste disposal workers.	2007 Jan	17366828
[Efficiency local injection therapy with preparation mydocalm in myofascial pain syndrome cervicobrachial region].	2009	19688873
NMR analysis, protonation equilibria and decomposition kinetics of tolperisone.	2009 Dec 5	19577875
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Differential effects of painful and non-painful stimulation on tactile processing in fibromyalgia syndrome and subjects with masochistic behaviour.	2010 Dec 28	21203391

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

In Vitro Use Guide

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.

Name

Type

Language

TOLPERISONE HYDROCHLORIDE

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

ABBSA

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