TOLPERISONE

Possibly Marketed Outside US

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Inhibitor 8,297		198.0 µM [IC50]
Voltage-gated calcium channel 37	Inhibitor 8,297		1062.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Muscle hypertonia 3	Primary		Approved 8,429	Mydocalm

C_max

Value	Dose	Analyte	Population
297.6 ng/mL	450 mg single, oral	TOLPERISONE plasma	Homo sapiens
64.1 ng/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
90.88 ng/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
229.47 ng/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
54 ng/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
98.85 ng/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
205.2 ng/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
70.89 ng/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
115.44 ng/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
516 ng × h/mL	450 mg single, oral	TOLPERISONE plasma	Homo sapiens
111.2 ng × h/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
151.92 ng × h/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
682.03 ng × h/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
81.09 ng × h/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
170.2 ng × h/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
274.6 ng × h/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
101.11 ng × h/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
194.63 ng × h/mL	150 mg single, oral	TOLPERISONE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.14 h	450 mg single, oral	TOLPERISONE plasma	Homo sapiens
3.3 h	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
2.7 h	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
2.66 h	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
2.91 h	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
2.33 h	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
2.82 h	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
2.84 h	150 mg single, oral	TOLPERISONE plasma	Homo sapiens
2.44 h	150 mg single, oral	TOLPERISONE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
900 mg 3 times / day multiple, oral Highest studied dose	unhealthy, ADULT
15000 mg single, oral Overdose	unknown, ADULT	Other AEs: Apnoea, Myoclonus...
25 mg single, oral Studied dose	unhealthy, ADULT	Other AEs: Urticaria, Anxiety...
2700 mg single, oral Accidental dose	healthy, CHILD	Other AEs: Seizures, Apnoea...

Showing 1 to 4 of 4 entries

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AEs

Show entries

AE	Dose	Population
Apnoea	15000 mg single, oral Overdose	unknown, ADULT
Hypotension	15000 mg single, oral Overdose	unknown, ADULT
Myoclonus	15000 mg single, oral Overdose	unknown, ADULT
Tachycardia	15000 mg single, oral Overdose	unknown, ADULT
Anxiety	25 mg single, oral Studied dose	unhealthy, ADULT

Showing 1 to 5 of 12 entries

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PubMed

Show entries

Title	Date	PubMed
[Convulsive mechanism of ketamine anesthesia].	1975 Aug	1198863
[Two complex suicidal poisonings with drugs and their medicolegal aspects].	2001	11450365
Tolperisone--a novel modulator of ionic currents in myelinated axons.	2001 Dec	11989651
Method for recording spinal reflexes in mice: effects of thyrotropin-releasing hormone, DOI, tolperisone and baclofen on monosynaptic spinal reflex potentials.	2001 May	11430467
[Patient with chronic backache. Disabled or muscle spasm patient?].	2002 Dec 5	12577750

Showing 1 to 5 of 12 entries

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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.