TOLPERISONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H23NO
Molecular Weight	245.3599
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FSKFPVLPFLJRQB-UHFFFAOYSA-N

InChI=1S/C16H23NO/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

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	( + / - )

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
[Convulsive mechanism of ketamine anesthesia].	1975 Aug	1198863
Simultaneous determination of tolperisone and lidocaine by high performance liquid chromatography.	2001 Dec	11600298
Method for recording spinal reflexes in mice: effects of thyrotropin-releasing hormone, DOI, tolperisone and baclofen on monosynaptic spinal reflex potentials.	2001 May	11430467
[Mydocalm causing anaphylaxis].	2003	14587432
Effect of muscle relaxants on experimental jaw-muscle pain and jaw-stretch reflexes: a double-blind and placebo-controlled trial.	2003	12935797
Prophylactic tolperisone for post-exercise muscle soreness causes reduced isometric force--a double-blind randomized crossover control study.	2003	12935792
[Spinal pain and its treatment with midocalm].	2003	12847906
Separation of basic drug enantiomers by capillary electrophoresis using chicken alpha1-acid glycoprotein: insight into chiral recognition mechanism.	2003 Aug	12900854
Anaphylactic reactions to tolperisone (Mydocalm).	2003 Jun 28	12947534
Simultaneous micellar LC determination of lidocaine and tolperisone.	2003 Mar 26	12644189
Identification of metabolic pathways involved in the biotransformation of tolperisone by human microsomal enzymes.	2003 May	12695352
[A study of mydocalm efficiency in the treatment of chronic headache of tension].	2005	16450434
Simple pharmacological test battery to assess efficacy and side effect profile of centrally acting muscle relaxant drugs.	2005 Sep-Oct	16125625
[A randomized, double blind, placebo-controlled study of the efficacy and safety of tolperisone in spasticity following cerebral stroke].	2006	16457132
HPLC determination of tolperisone in human plasma.	2006 Apr	16681042
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
[Post-operative pain therapy of a chronic pain patient].	2006 Nov	17151986
[Comparative effciency of bakloferon and tolperizon central muscle relaxants in complex therapy of back pain].	2006 Sep	17180860
[Use of local injections of tolperisone (midocalm) in combination with tractional therapy in the treatment of vertebral static syndrome].	2007	18379519
Determination of eperisone in human plasma by liquid chromatography-ESI-tandem mass spectrometry.	2007 Sep	17958338
[New therapies for spastic movement disorders].	2009 Oct	20623938
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:07:10 GMT 2023` Edited by `admin` on `Fri Dec 15 16:07:10 GMT 2023`
Record UNII	F5EOM0LD8E
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TOLPERISONE

Official Name

English

N-553 FREE BASE

Code

English

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

Systematic Name

English

2,4'-DIMETHYL-3-PIPERIDINOPROPIOPHENONE

Systematic Name

English

TOLPERISONE [MI]

Common Name

English

2-METHYL-3-PIPERIDINO-1-P-TOLYLPROPAN-1-ONE

Common Name

English

NSC-107321

Code

English

tolperisone [INN]

Common Name

English

1-PIPERIDINO-2-METHYL-3-(P-TOLYL)-3-PROPANONE

Common Name

English

Tolperisone [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29696