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{{Short description|Chemical compound}}
{{Use mdy dates|date=April 2024}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | verifiedrevid = 446484818
| Watchedfields = changed
⚫ | IUPAC_name = ''N''-heptalen-7-yl]acetamide
⚫ | verifiedrevid = 448013724
⚫ | IUPAC_name = ''N''-heptalen-7-yl]ethanamide
| image = Thiocolchicoside.png | image = Thiocolchicoside.png


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| Drugs.com = {{drugs.com|international|thiocolchicoside}} | Drugs.com = {{drugs.com|international|thiocolchicoside}}
| legal_status = Rx-only | legal_status = Rx-only
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<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 25%<ref name="pmid8983937">{{cite journal | author = Perucca E, Poitou P, Pifferi G | title = Comparative pharmacokinetics and bioavailability of two oral formulations of thiocolchicoside, a GABA-mimetic muscle relaxant drug, in normal volunteers | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 20 | issue = 4 | pages = 301–5 | year = 1995 | pmid = 8983937 | doi = | url = }}</ref> | bioavailability = 25%<ref name="pmid8983937">{{cite journal | vauthors = Perucca E, Poitou P, Pifferi G | title = Comparative pharmacokinetics and bioavailability of two oral formulations of thiocolchicoside, a GABA-mimetic muscle relaxant drug, in normal volunteers | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 20 | issue = 4 | pages = 301–5 | year = 1995 | pmid = 8983937 | doi = 10.1007/bf03190249 | s2cid = 13325496 }}</ref>
| elimination_half-life = 5-6 hours<ref name="pmid8983937"/><ref name="pmid8161719">{{cite journal | author = Sandouk P, Bouvier d'Yvoire M, Chretien P, Tillement JP, Scherrmann JM | title = Single-dose bioavailability of oral and intramuscular thiocolchicoside in healthy volunteers | journal = Biopharmaceutics & Drug Disposition | volume = 15 | issue = 1 | pages = 87–92 | year = 1994 | month = January | pmid = 8161719 | doi = | url = }}</ref> | elimination_half-life = 5-6 hours<ref name="pmid8983937"/><ref name="pmid8161719">{{cite journal | vauthors = Sandouk P, Bouvier d'Yvoire M, Chretien P, Tillement JP, Scherrmann JM | title = Single-dose bioavailability of oral and intramuscular thiocolchicoside in healthy volunteers | journal = Biopharmaceutics & Drug Disposition | volume = 15 | issue = 1 | pages = 87–92 | date = January 1994 | pmid = 8161719 | doi = 10.1002/bdd.2510150108 | s2cid = 6712875 }}</ref>


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 602-41-5 | CAS_number = 602-41-5
| ATC_prefix = M03 | ATC_prefix = M03
| ATC_suffix = BX05 | ATC_suffix = BX05
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB11582
| PubChem = 72067 | PubChem = 72067
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1705373
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = T1X8S697GT | UNII = T1X8S697GT
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07276 | KEGG = D07276
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8091534


<!--Chemical data--> <!--Chemical data-->
| C=27 | H=33 | N=1 | O=10 | S=1 | C=27 | H=33 | N=1 | O=10 | S=1
| molecular_weight = 563.618 g/mol
| smiles = O=C(N4C1=C\C(=O)C(/SC)=C\C=C1c3c(cc(O2O((O)(O)2O)CO)c(OC)c3OC)CC4)C | smiles = O=C(N4C1=C\C(=O)C(/SC)=C\C=C1c3c(cc(O2O((O)(O)2O)CO)c(OC)c3OC)CC4)C
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C27H33NO10S/c1-12(30)28-16-7-5-13-9-18(37-27-24(34)23(33)22(32)19(11-29)38-27)25(35-2)26(36-3)21(13)14-6-8-20(39-4)17(31)10-15(14)16/h6,8-10,16,19,22-24,27,29,32-34H,5,7,11H2,1-4H3,(H,28,30)/t16-,19+,22+,23-,24+,27+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = LEQAKWQJCITZNK-AXHKHJLKSA-N
}} }}


'''Thiocolchicoside''' ('''Muscoril''', '''Myoril''', '''Neoflax''') is a ] with ] and ] effects.<ref name="pmid14563464">{{cite journal | author = Tüzün F, Unalan H, Oner N, ''et al.'' | title = Multicenter, randomized, double-blinded, placebo-controlled trial of thiocolchicoside in acute low back pain | journal = Joint, Bone, Spine : Revue Du Rhumatisme | volume = 70 | issue = 5 | pages = 356–61 | year = 2003 | month = September | pmid = 14563464 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/S1297319X03000757}}</ref><ref name="pmid19780000">{{cite journal | author = Ketenci A, Basat H, Esmaeilzadeh S | title = The efficacy of topical thiocolchicoside (Muscoril) in the treatment of acute cervical myofascial pain syndrome: a single-blind, randomized, prospective, phase IV clinical study | journal = Journal of the Turkish Society of Algology | volume = 21 | issue = 3 | pages = 95–103 | year = 2009 | month = July | pmid = 19780000 | doi = | url = http://www.journalagent.com/pubmed/linkout.asp?ISSN=1300-0012&PMID=19780000}}</ref><ref name="pmid18839644">{{cite journal | author = Soonawalla DF, Joshi N | title = Efficacy of thiocolchicoside in Indian patients suffering from low back pain associated with muscle spasm | journal = Journal of the Indian Medical Association | volume = 106 | issue = 5 | pages = 331–5 | year = 2008 | month = May | pmid = 18839644 | doi = | url = }}</ref><ref name="pmid15963201">{{cite journal | author = Ketenci A, Ozcan E, Karamursel S | title = Assessment of efficacy and psychomotor performances of thiocolchicoside and tizanidine in patients with acute low back pain | journal = International Journal of Clinical Practice | volume = 59 | issue = 7 | pages = 764–70 | year = 2005 | month = July | pmid = 15963201 | doi = 10.1111/j.1742-1241.2004.00454.x | url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1368-5031&date=2005&volume=59&issue=7&spage=764}}</ref> It acts as a ] ] ] and also inhibits ]s with similar ] and ]s to a much lesser extent.<ref name="pmid16806306">{{cite journal | author = Carta M, Murru L, Botta P, ''et al.'' | title = The muscle relaxant thiocolchicoside is an antagonist of GABAA receptor function in the central nervous system | journal = Neuropharmacology | volume = 51 | issue = 4 | pages = 805–15 | year = 2006 | month = September | pmid = 16806306 | doi = 10.1016/j.neuropharm.2006.05.023 | url = http://linkinghub.elsevier.com/retrieve/pii/S0028-3908(06)00148-1}}</ref><ref name="pmid17234181">{{cite journal | author = Mascia MP, Bachis E, Obili N, ''et al.'' | title = Thiocolchicoside inhibits the activity of various subtypes of recombinant GABA(A) receptors expressed in Xenopus laevis oocytes | journal = European Journal of Pharmacology | volume = 558 | issue = 1-3 | pages = 37–42 | year = 2007 | month = March | pmid = 17234181 | doi = 10.1016/j.ejphar.2006.11.076 | url = http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(06)01380-X}}</ref> It has powerful ] activity and should not be used in ]-prone individuals.<ref name="pmid11554898">{{cite journal | author = De Riu PL, Rosati G, Sotgiu S, Sechi G | title = Epileptic seizures after treatment with thiocolchicoside | journal = Epilepsia | volume = 42 | issue = 8 | pages = 1084–6 | year = 2001 | month = August | pmid = 11554898 | doi = 10.1046/j.1528-1157.2001.0420081084.x| url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0013-9580&date=2001&volume=42&issue=8&spage=1084}}</ref><ref name="pmid19707540">{{cite journal | author = Giavina-Bianchi P, Giavina-Bianchi M, Tanno LK, Ensina LF, Motta AA, Kalil J | title = Epileptic seizure after treatment with thiocolchicoside | journal = Therapeutics and Clinical Risk Management | volume = 5 | issue = 3 | pages = 635–7 | year = 2009 | month = June | pmid = 19707540 | pmc = 2731019 | doi = | url = http://www.dovepress.com/articles.php?article_id=3422}}</ref><ref name="pmid12967581">{{cite journal | author = Sechi G, De Riu P, Mameli O, Deiana GA, Cocco GA, Rosati G | title = Focal and secondarily generalised convulsive status epilepticus induced by thiocolchicoside in the rat | journal = Seizure : the Journal of the British Epilepsy Association | volume = 12 | issue = 7 | pages = 508–15 | year = 2003 | month = October | pmid = 12967581 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/S1059131103000530}}</ref> '''Thiocolchicoside''' ('''Muscoril''', '''Myoril''', '''Neoflax''') is a ] with ] and ] effects.<ref name="pmid14563464">{{cite journal | vauthors = Tüzün F, Unalan H, Oner N, Ozgüzel H, Kirazli Y, Içağasioğlu A, Kuran B, Tüzün S, Başar G | title = Multicenter, randomized, double-blinded, placebo-controlled trial of thiocolchicoside in acute low back pain | journal = Joint, Bone, Spine | volume = 70 | issue = 5 | pages = 356–61 | date = September 2003 | pmid = 14563464 | doi = 10.1016/S1297-319X(03)00075-7 }}</ref><ref name="pmid19780000">{{cite journal | vauthors = Ketenci A, Basat H, Esmaeilzadeh S | title = The efficacy of topical thiocolchicoside (Muscoril) in the treatment of acute cervical myofascial pain syndrome: a single-blind, randomized, prospective, phase IV clinical study | journal = Agri | volume = 21 | issue = 3 | pages = 95–103 | date = July 2009 | pmid = 19780000 | url = http://www.journalagent.com/pubmed/linkout.asp?ISSN=1300-0012&PMID=19780000 | access-date = April 8, 2010 | archive-date = December 15, 2019 | archive-url = https://web.archive.org/web/20191215233829/http://www.journalagent.com/pubmed/linkout.asp?ISSN=1300-0012&PMID=19780000 | url-status = live }}</ref><ref name="pmid18839644">{{cite journal | vauthors = Soonawalla DF, Joshi N | title = Efficacy of thiocolchicoside in Indian patients suffering from low back pain associated with muscle spasm | journal = Journal of the Indian Medical Association | volume = 106 | issue = 5 | pages = 331–5 | date = May 2008 | pmid = 18839644 }}</ref><ref name="pmid15963201">{{cite journal | vauthors = Ketenci A, Ozcan E, Karamursel S | title = Assessment of efficacy and psychomotor performances of thiocolchicoside and tizanidine in patients with acute low back pain | journal = International Journal of Clinical Practice | volume = 59 | issue = 7 | pages = 764–70 | date = July 2005 | pmid = 15963201 | doi = 10.1111/j.1742-1241.2004.00454.x | s2cid = 20671452 | doi-access = free }}</ref> Its mechanism of action is unknown, but it is believed to be act via ] of ]s (nAchRs). However, it also appears to be a ] antagonist of ] and ].<ref name="pmid16806306">{{cite journal | vauthors = Carta M, Murru L, Botta P, Talani G, Sechi G, De Riu P, Sanna E, Biggio G | title = The muscle relaxant thiocolchicoside is an agonist of GABAA receptor function in the central nervous system | journal = Neuropharmacology | volume = 51 | issue = 4 | pages = 805–15 | date = September 2006 | pmid = 16806306 | doi = 10.1016/j.neuropharm.2006.05.023 | s2cid = 11390033 }}</ref><ref name="pmid17234181">{{cite journal | vauthors = Mascia MP, Bachis E, Obili N, Maciocco E, Cocco GA, Sechi GP, Biggio G | title = Thiocolchicoside inhibits the activity of various subtypes of recombinant GABA(A) receptors expressed in Xenopus laevis oocytes | journal = European Journal of Pharmacology | volume = 558 | issue = 1–3 | pages = 37–42 | date = March 2007 | pmid = 17234181 | doi = 10.1016/j.ejphar.2006.11.076 }}</ref> As such, it has powerful ] activity and should not be used in ]-prone individuals.<ref name="pmid11554898">{{cite journal | vauthors = De Riu PL, Rosati G, Sotgiu S, Sechi G | title = Epileptic seizures after treatment with thiocolchicoside | journal = Epilepsia | volume = 42 | issue = 8 | pages = 1084–6 | date = August 2001 | pmid = 11554898 | doi = 10.1046/j.1528-1157.2001.0420081084.x | s2cid = 24017279 | doi-access = free }}</ref><ref name="pmid19707540">{{cite journal | vauthors = Giavina-Bianchi P, Giavina-Bianchi M, Tanno LK, Ensina LF, Motta AA, Kalil J | title = Epileptic seizure after treatment with thiocolchicoside | journal = Therapeutics and Clinical Risk Management | volume = 5 | issue = 3 | pages = 635–7 | date = June 2009 | pmid = 19707540 | pmc = 2731019 | doi = 10.2147/tcrm.s4823 | doi-access = free }}</ref><ref name="pmid12967581">{{cite journal | vauthors = Sechi G, De Riu P, Mameli O, Deiana GA, Cocco GA, Rosati G | title = Focal and secondarily generalised convulsive status epilepticus induced by thiocolchicoside in the rat | journal = Seizure | volume = 12 | issue = 7 | pages = 508–15 | date = October 2003 | pmid = 12967581 | doi = 10.1016/S1059-1311(03)00053-0 | s2cid = 14308541 | doi-access = free }}</ref>
== Medical uses ==
=== Low back pain ===
In low back pain, thiocolchicoside is efficacious in reducing pain intensity, improving physical flexibility as seen in decreasing the distance from the hands to the floor when leaning forward without bending the knees (finger-floor distance), and reducing the total consumption of ].<ref name="pmid32064669"/> Thiocolchicoside administration also leads to a reduction in muscle spasm during palpation, an improvement in the overall assessment of patients with low back pain, and an enhancement in their ability to perform daily activities.<ref name="pmid32064669">{{cite journal |vauthors=Patel M, Shah R, Ramteke-Jadhav S, Patil V, Patel SK, Lila A, Shah N, Bandgar T |trans-title=Management of Insulin Autoimmune Hypoglycaemia: Single-centre experience from Western India with systematic review of world literature |journal=Clin Endocrinol (Oxf) |volume=92 |issue=5 |pages=409–420 |date=May 2020 |pmid=32064669 |doi=10.1111/cen.14174 |doi-access=free|language=ru|title=Систематический обзор по применению миорелаксантов при боли в нижней части спины}}</ref><ref name="pmid27065070"/>

When thiocolchicoside is added to standard ] (NSAID) therapy in lower back pain, such therapy reduces pain intensity and improves functional status according to the average estimates of ] (VAS) and life disorders questionnaires. The use of thiocolchicoside in combination with NSAIDs results in a more pronounced decrease in pain when assessed by VAS, as well as an increase in functional activity based on an estimate of the distance from the fingertips to the floor by the 7th day of therapy (but not by the 3rd) compared with the use of NSAIDs alone.<ref name="pmid32064669"/><ref name="pmid27065070"/>

Several medicines, including ], ] plus ], and ], are effective in reducing pain intensity. Another comparative study found that ] with ] was more effective in terms of finger-floor distance and improvement in ] (straight leg raise angle laying on back), VAS score, and global assessment scale than thiocolchicoside with diclofenac.<ref name="pmid32064669"/><ref name="pmid27065070">{{cite journal |vauthors=Petousis S, Margioula-Siarkou C, Kalogiannidis I |title=Effectiveness of Tocolytic Agents on Prevention of Preterm Delivery, Neonatal Morbidity, and Mortality: Is There a Consensus? A Review of the Literature |journal=Obstet Gynecol Surv |volume=71 |issue=4 |pages=243–52 |date=April 2016 |pmid=27065070 |doi=10.1097/OGX.0000000000000302}}</ref><ref name="pmid35706494">{{cite journal |vauthors=Qin Z, Zhang C, Guo J, Kwong JS, Li X, Pang R, Doiron RC, Nickel JC, Wu J |title=Oral pharmacological treatments for chronic prostatitis/chronic pelvic pain syndrome: A systematic review and network meta-analysis of randomised controlled trials |journal=eClinicalMedicine |volume=48 |issue= |pages=101457 |date=June 2022 |pmid=35706494 |pmc=9125656 |doi=10.1016/j.eclinm.2022.101457}}</ref>


== Side effects == == Side effects ==
Side effects of thiocolchicoside can include nausea, allergy and ] reactions.<ref name="pmid21552685">{{cite journal | vauthors = Efe C, Purnak T, Ozaslan E, Milanlioglu A | title = Thiocolchicoside-induced liver injury | journal = Clinics | volume = 66 | issue = 3 | pages = 521–2 | date = Mar 2011 | pmid = 21552685 | pmc = 3072020 | doi = 10.1590/s1807-59322011000300029 }}</ref>
Liver injury, ], seizures, blood cell disorders, ], ], and reproductive disorders have all been recorded in the French and European ] databases and in the periodic updates that the companies concerned submit to regulatory agencies. These data do not specify the frequency of the disorders nor do they identify the most susceptible patient populations. Thiocolchicoside is ] in experimental animals and also damages chromosomes. Human data are limited to a follow-up of about 30 pregnant women (no major malformations) and reports of altered spermatogenesis, including cases of ]. In practice, there is no justification for exposing patients to the adverse effects of thiocolchicoside. It is better to use an effective, well-known analgesic for patients complaining of muscle pain, starting with ].<ref name="pmid27042729">{{cite journal | title = Thiocolchicoside: review of adverse effects | journal = Prescrire International | volume = 25 | issue = 168 | pages = 41–3 | date = February 2016 | pmid = 27042729 }}</ref>


Although muscle relaxants may have the major side effect of sedation, thiocolchicoside is free from sedation effects, likely due to its lack of potentiation of ] receptors.<ref name="pmid16806306" />
Side effect of skeletal muscle relaxants may include: sedation, drowsiness, blurred or double vision,
constipation or diarrhea, dizziness and drowsiness, nervousness and confusion, dry mouth, dyspepsia (chronic or recurrent pain in the upper abdomen, upper abdominal fullness, and feeling full earlier than expected when eating), fatigue, headache, heartburn, hiccups and nausea, insomnia, stomach cramps, trembling, vomiting, and weakness; and possible dependence following long-term use.


==Pharmacokinetics==
⚫ ==References==
Thiocolchicoside is broken down in the body to a ] called ] (also known as SL59.0955 or M2) that could damage dividing cells therefore inducing toxicity in the embryo, neoplastic changes and fertility reduction in males.<ref name="EMA-thiocolchicoside-2024-restrict">{{cite web | url=https://www.ema.europa.eu/en/news/european-medicines-agency-recommends-restricting-use-thiocolchicoside-mouth-or-injection | title=European Medicines Agency recommends restricting use of thiocolchicoside by mouth or injection | date=November 22, 2013 | access-date=2024-05-25 | archive-date=2024-04-21 | archive-url=https://web.archive.org/web/20240421104947/https://www.ema.europa.eu/en/news/european-medicines-agency-recommends-restricting-use-thiocolchicoside-mouth-or-injection | url-status=live }}</ref> Therefore, recommended oral dose should not exceed 7 days and intramuscular dose duration should not exceed 5 days.<ref name="EMA-thiocolchicoside-2018-contain">{{cite web|url=http://www.aifa.gov.it/en/content/thiocolchicoside-containing-products-systemic-use-important-information-regarding-indication|archive-url=https://web.archive.org/web/20190521231101/http://www.aifa.gov.it/en/content/thiocolchicoside-containing-products-systemic-use-important-information-regarding-indication|title=Thiocolchicoside-containing products for systemic use - important information regarding indications, treatment regimen, contraindications and warnings|date=February 7, 2024|archive-date=May 21, 2019}}</ref> Local skin preparations are less toxic.{{medical citation needed|date=April 2024}}

⚫ == References ==
{{Reflist}} {{Reflist}}


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{{Analgesics}} {{Analgesics}}
{{Anti-inflammatory}} {{Anti-inflammatory}}
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