Tolperisone: Difference between revisions

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{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451425253
| IUPAC_name = 2-methyl-1-(4-methylphenyl)-3-(1-piperidyl)propan-1-one
| IUPAC_name = 2-methyl-1-(4-methylphenyl)-3-(1-piperidyl)propan-1-one
| image=Tolperisone.svg
| image = Tolperisone-2d-skeletal.png
| width = 120
| width = 150
| CAS_number=728-88-1
 
| ATC_prefix=M03
<!--Clinical data-->
| ATC_suffix=BX04
| tradename = Mydocalm and others
| ATC_supplemental=
| Drugs.com = {{drugs.com|international|tolperisone}}
| PubChem=5511
| pregnancy_category=
| DrugBank=
| legal_status      = Rx-only
| C = 16 | H = 23 | N = 1 | O = 1
| routes_of_administration = Oral, [[parenteral]]
 
<!-- Pharmacokinetic data -->
| bioavailability  =
| protein_bound    =
| metabolism        = Liver, kidney
| elimination_half-life = 1st phase: 2 hrs<br />2nd phase: 12 hrs
| excretion        = [[Kidney|Renal]]
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 728-88-1
| ATC_prefix = M02
| ATC_suffix = AX06
| ATC_supplemental = {{ATC|M03|BX04}}
| PubChem = 5511
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1076211
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = F5EOM0LD8E
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08617
 
<!--Chemical data-->
| C=16 | H=23 | N=1 | O=1  
| molecular_weight = 245.36 g/mol
| molecular_weight = 245.36 g/mol
| bioavailability=  
| smiles = C1CCCN(C1)CC(C(C2=CC=C(C=C2)C)=O)C
| metabolism =  
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| elimination_half-life=
| StdInChI = 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
| excretion =
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| pregnancy_category =
| StdInChIKey = FSKFPVLPFLJRQB-UHFFFAOYSA-N
| legal_status =
| routes_of_administration=  
}}
}}
__NOTOC__
'''Tolperisone''', a [[piperidine]] derivative, is a centrally acting [[muscle relaxant]]. Trade names include '''Biocalm''', '''Muscodol''', '''Mydeton''', '''Mydocalm''', '''Myolax''', '''Myoxan''' and '''Viveo'''.
{{SI}}
 
{{CMG}}
== Clinical use ==
In Tolperisone is indicated for use in the treatment of pathologically increased tone of the cross-striated muscle caused by neurological diseases (damage of the [[pyramidal tract]], [[multiple sclerosis]], [[myelopathy]], [[encephalomyelitis]]) and of spastic paralysis and other encephalopathies manifested with muscular dystonia.<ref name="Austria-Codex">{{cite book|title=Austria-Codex|editor=Jasek, W|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2007|edition=62nd|pages=5510–1|isbn=978-3-85200-181-4|language=German}}</ref><ref name="Midocalm-ro">{{ cite web | url = http://www.info-medic.ro/midocalm/ | title = Midocalm | publisher = InfoMedic| location = Romania}}</ref>
 
Other possible uses include:{{fact|date=May 2012}}
*[[Spondylosis]]
*Spondylarthrosis
*Cervical and lumbar syndromes
*[[Arthrosis]] of the large joints
*[[atherosclerosis|Obliterating atherosclerosis]] of the extremity vessels
*[[Diabetic angiopathy]]
*[[Thromboangiitis obliterans]]
*[[Raynaud's syndrome]]
 
== Contraindications and cautions ==
Manufacturers report that tolperisone should not be used in patients with [[myasthenia gravis]]. Only limited data are available regarding the safety in children, youths, during pregnancy and breastfeeding. It is not known whether tolperisone is excreted into mother's milk.<ref name="Austria-Codex" /><ref name="Midocalm-ro" />
 
== Side effects  ==
Adverse effects occur in fewer than 1% of patients and include muscle weakness, headache, arterial [[hypotension]], nausea, vomiting, [[dyspepsia]], and dry mouth. All effects are reversible.<ref name="Austria-Codex" /><ref name="Midocalm-ro" />
Allergic reactions occur in fewer than 0.1% of patient and include skin rash, [[hives]], [[Quincke's edema]], and in some cases [[anaphylactic shock]].<ref name="Austria-Codex" /><ref>{{ cite journal | author = Ribi C, Vermeulen C, Hauser C | title = Anaphylactic reactions to tolperisone (Mydocalm) | journal = Swiss Medical Weekly | volume = 133 | issue = 25–26 | pages = 369–371 | year = 2003 | pmid = 12947534 }}</ref><ref name="pmid14587432">{{cite journal |author=Kwaśniewski A, Korbuszewska-Gontarz B, Mika S |title=[Mydocalm causing anaphylaxis] |language=Polish |journal=Pneumonol Alergol Pol |volume=71 |issue=5-6 |pages=250–2 |year=2003 |pmid=14587432 |doi= |url= |accessdate=2014-12-17}}</ref><ref name="pmid21905508">{{cite journal |author=Glück J, Rymarczyk B, Rogala B |title=An immediate hypersensitivity reaction caused by tolperisone hydrochloride |journal=J Investig Allergol Clin Immunol |volume=21 |issue=5 |pages=411–2 |year=2011 |pmid=21905508 |doi= |url= |accessdate=2014-12-17}}</ref>
 
== Overdose ==
Excitability has been noted after ingestion of high doses by children.<ref name="Austria-Codex" />
In suicide studies of three isolated cases, it is believed that ingestion of tolperisone was the cause of death.<ref>{{ cite journal | author = Sporkert, F.; Brunel, C.; Augsburger, M. P.; Mangin, P. | title = Fatal tolperisone poisoning: Autopsy and toxicology findings in three suicide cases | journal = Forensic Science International | year = 2012 | volume = 215 | issue = 1 | pages = 101–104 | doi = 10.1016/j.forsciint.2011.05.025 | pmid = 21683537 }}</ref>
 
== Interactions ==
Tolperisone does not have a significant potential for interactions with other pharmaceutical drugs. It cannot be excluded that combination with other centrally acting muscle relaxants, [[benzodiazepine]]s or [[non-steroidal anti-inflammatory drug]]s (NSAIDs) may make a dose reduction necessary in some patients.<ref name="Austria-Codex" /><ref name="Midocalm-ro" />
 
== Mechanism of action ==
Tolperisone is a centrally acting muscle relaxant that acts at the [[reticular formation]] in the brain stem<ref name="Austria-Codex" /> by blocking [[Voltage-gated sodium channel|voltage-gated sodium]] and [[Voltage-gated calcium channel|calcium channels]].<ref>{{ cite journal | author = Kocsis P, Farkas S, Fodor L, Bielik N, Thán M, Kolok S, Gere A, Csejtei M, Tarnawa I | title = Tolperisone-type drugs inhibit spinal reflexes via blockade of voltage-gated sodium and calcium channels | journal = Journal of Pharmacology and Experimental Therapeutics | volume = 315 | issue = 3 | pages = 1237–1246 | year = 2005 | pmid = 16126840 | doi = 10.1124/jpet.105.089805 }}</ref><ref>{{ cite journal | author = Hofer D, Lohberger B, Steinecker B, Schmidt K, Quasthoff S, Schreibmayer W | title = A comparative study of the action of tolperisone on seven different voltage dependent sodium channel isoforms | journal = European Journal of Pharmacology | volume = 538 | issue = 1–3 | pages = 5–14 | year = 2006 | pmid = 16650844 | doi = 10.1016/j.ejphar.2006.03.034 }}</ref>
 
== Pharmacokinetics ==
Tolperisone is absorbed nearly completely from the gut and reaches its [[peak (pharmacology)|peak]] blood plasma concentration after 1.5 hours. It is extensively metabolised in the liver and kidneys. The substance is excreted via the kidneys in two phases; the first with a half-life of two hours, and the second with a half-life of 12 hours.<ref name="Austria-Codex" />
 
== See also ==
* Chemically and mechanistically related drugs: [[eperisone]], [[inaperisone]], [[lanperisone]], [[silperisone]]


==Overview==
== References ==
'''Tolperisone''', a [[piperidine]] derivative, is a centrally acting [[muscle relaxant]]. Brand names include '''Mydocalm''' and '''Mydeton'''.
{{reflist|2}}


==External links==
== External links ==
* {{cite journal | author = Hofer D, Lohberger B, Steinecker B, Schmidt K, Quasthoff S, Schreibmayer W | title = A comparative study of the action of tolperisone on seven different voltage dependent sodium channel isoforms. | journal = Eur J Pharmacol | volume = 538 | issue = 1-3 | pages = 5-14 | year = 2006 | id = PMID 16650844}}
* {{ cite web | url = http://lib.bioinfo.pl/meid:189350 | title = Tolperisone: Administration & Dosage - Papers | publisher = BioInfo | location = Poland }}{{dead link|date=December 2013}}
* {{cite journal | author = Kocsis P, Farkas S, Fodor L, Bielik N, Thán M, Kolok S, Gere A, Csejtei M, Tarnawa I | title = Tolperisone-type drugs inhibit spinal reflexes via blockade of voltage-gated sodium and calcium channels. | journal = J Pharmacol Exp Ther | volume = 315 | issue = 3 | pages = 1237-46 | year = 2005 | id = PMID 16126840}}
* {{cite journal | author = Ribi C, Vermeulen C, Hauser C | title = Anaphylactic reactions to tolperisone (Mydocalm). | journal = Swiss Med Wkly | volume = 133 | issue = 25-26 | pages = 369-71 | year = 2003 | id = PMID 12947534}}


{{Muscle relaxants}}
{{Muscle relaxants}}


[[Category:Drug]]
[[Category:Drug]]
[[Category:Piperidines]]
[[Category:Muscle relaxants]]
[[Category:Aromatic ketones]]

Revision as of 12:50, 10 April 2015

Tolperisone
Clinical data
Trade namesMydocalm and others
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, parenteral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismLiver, kidney
Elimination half-life1st phase: 2 hrs
2nd phase: 12 hrs
ExcretionRenal
Identifiers
CAS Number
PubChem CID
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC16H23NO
Molar mass245.36 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Tolperisone, a piperidine derivative, is a centrally acting muscle relaxant. Trade names include Biocalm, Muscodol, Mydeton, Mydocalm, Myolax, Myoxan and Viveo.

Clinical use

In Tolperisone is indicated for use in the treatment of pathologically increased tone of the cross-striated muscle caused by neurological diseases (damage of the pyramidal tract, multiple sclerosis, myelopathy, encephalomyelitis) and of spastic paralysis and other encephalopathies manifested with muscular dystonia.[1][2]

Other possible uses include:[citation needed]

Contraindications and cautions

Manufacturers report that tolperisone should not be used in patients with myasthenia gravis. Only limited data are available regarding the safety in children, youths, during pregnancy and breastfeeding. It is not known whether tolperisone is excreted into mother's milk.[1][2]

Side effects

Adverse effects occur in fewer than 1% of patients and include muscle weakness, headache, arterial hypotension, nausea, vomiting, dyspepsia, and dry mouth. All effects are reversible.[1][2] Allergic reactions occur in fewer than 0.1% of patient and include skin rash, hives, Quincke's edema, and in some cases anaphylactic shock.[1][3][4][5]

Overdose

Excitability has been noted after ingestion of high doses by children.[1] In suicide studies of three isolated cases, it is believed that ingestion of tolperisone was the cause of death.[6]

Interactions

Tolperisone does not have a significant potential for interactions with other pharmaceutical drugs. It cannot be excluded that combination with other centrally acting muscle relaxants, benzodiazepines or non-steroidal anti-inflammatory drugs (NSAIDs) may make a dose reduction necessary in some patients.[1][2]

Mechanism of action

Tolperisone is a centrally acting muscle relaxant that acts at the reticular formation in the brain stem[1] by blocking voltage-gated sodium and calcium channels.[7][8]

Pharmacokinetics

Tolperisone is absorbed nearly completely from the gut and reaches its peak blood plasma concentration after 1.5 hours. It is extensively metabolised in the liver and kidneys. The substance is excreted via the kidneys in two phases; the first with a half-life of two hours, and the second with a half-life of 12 hours.[1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 Jasek, W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 5510–1. ISBN 978-3-85200-181-4.
  2. ↑ 2.0 2.1 2.2 2.3 "Midocalm". Romania: InfoMedic.
  3. ↑ Ribi C, Vermeulen C, Hauser C (2003). "Anaphylactic reactions to tolperisone (Mydocalm)". Swiss Medical Weekly. 133 (25–26): 369–371. PMID 12947534.
  4. ↑ Kwaśniewski A, Korbuszewska-Gontarz B, Mika S (2003). "[Mydocalm causing anaphylaxis]". Pneumonol Alergol Pol (in Polish). 71 (5–6): 250–2. PMID 14587432. |access-date= requires |url= (help)
  5. ↑ Glück J, Rymarczyk B, Rogala B (2011). "An immediate hypersensitivity reaction caused by tolperisone hydrochloride". J Investig Allergol Clin Immunol. 21 (5): 411–2. PMID 21905508. |access-date= requires |url= (help)
  6. ↑ Sporkert, F.; Brunel, C.; Augsburger, M. P.; Mangin, P. (2012). "Fatal tolperisone poisoning: Autopsy and toxicology findings in three suicide cases". Forensic Science International. 215 (1): 101–104. doi:10.1016/j.forsciint.2011.05.025. PMID 21683537.
  7. ↑ Kocsis P, Farkas S, Fodor L, Bielik N, Thán M, Kolok S, Gere A, Csejtei M, Tarnawa I (2005). "Tolperisone-type drugs inhibit spinal reflexes via blockade of voltage-gated sodium and calcium channels". Journal of Pharmacology and Experimental Therapeutics. 315 (3): 1237–1246. doi:10.1124/jpet.105.089805. PMID 16126840.
  8. ↑ Hofer D, Lohberger B, Steinecker B, Schmidt K, Quasthoff S, Schreibmayer W (2006). "A comparative study of the action of tolperisone on seven different voltage dependent sodium channel isoforms". European Journal of Pharmacology. 538 (1–3): 5–14. doi:10.1016/j.ejphar.2006.03.034. PMID 16650844.

External links

Retrieved from "https://www.wikidoc.org/index.php?title=Tolperisone&oldid=1085698"