Thiocolchicoside: Difference between revisions

Thiocolchicoside
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, Topical, IM
ATC code	M03BX05 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	25%
Elimination half-life	5-6 hours
Identifiers
	IUPAC name N-[(7S)-3-(β-D-Glucopyranosyloxy)-1,2-dimethoxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide;
CAS Number	602-41-5 ;
PubChem CID	72067;
UNII	T1X8S697GT;
KEGG	D07276 ;
ChEMBL	ChEMBL1705373 ;
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
Formula	C27H33NO10S
Molar mass	563.618 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(N[C@@H]4C1=C\C(=O)C(/SC)=C\C=C1c3c(cc(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)c(OC)c3OC)CC4)C;
	InChI InChI=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-/m1/s1 ; Key:LEQAKWQJCITZNK-MSQQGMGVSA-N ;
(what is this?) (verify)

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Healthcare Provider Resources
Symptoms of Thiocolchicoside Causes & Risk Factors for Thiocolchicoside Diagnostic studies for Thiocolchicoside Treatment of Thiocolchicoside
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Thiocolchicoside en Espanol Thiocolchicoside en Francais
Business
Thiocolchicoside in the Marketplace Patents on Thiocolchicoside
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Thiocolchicoside
Clinical data
ATC code	M03BX05 (WHO) ;
Identifiers
	IUPAC name N-[1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-benzo[d]heptalen-7-yl]acetamide;
PubChem CID	72067;
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
Formula	C27H33NO10S
Molar mass	563.618 g/mol

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VisualWikitext

Revision as of 17:36, 7 April 2015

Articles
WikiDoc Resources for Thiocolchicoside
Most recent articles on Thiocolchicoside Most cited articles on Thiocolchicoside Review articles on Thiocolchicoside Articles on Thiocolchicoside in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Thiocolchicoside Images of Thiocolchicoside Photos of Thiocolchicoside Podcasts & MP3s on Thiocolchicoside Videos on Thiocolchicoside
Evidence Based Medicine
Cochrane Collaboration on Thiocolchicoside Bandolier on Thiocolchicoside TRIP on Thiocolchicoside
Clinical Trials
Ongoing Trials on Thiocolchicoside at Clinical Trials.gov Trial results on Thiocolchicoside Clinical Trials on Thiocolchicoside at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Thiocolchicoside NICE Guidance on Thiocolchicoside NHS PRODIGY Guidance FDA on Thiocolchicoside CDC on Thiocolchicoside
Books
Books on Thiocolchicoside
News
Thiocolchicoside in the news Be alerted to news on Thiocolchicoside News trends on Thiocolchicoside
Commentary
Blogs on Thiocolchicoside
Definitions
Definitions of Thiocolchicoside
Patient Resources / Community
Patient resources on Thiocolchicoside Discussion groups on Thiocolchicoside Patient Handouts on Thiocolchicoside Directions to Hospitals Treating Thiocolchicoside Risk calculators and risk factors for Thiocolchicoside
Healthcare Provider Resources
Symptoms of Thiocolchicoside Causes & Risk Factors for Thiocolchicoside Diagnostic studies for Thiocolchicoside Treatment of Thiocolchicoside
Continuing Medical Education (CME)
CME Programs on Thiocolchicoside
International
Thiocolchicoside en Espanol Thiocolchicoside en Francais
Business
Thiocolchicoside in the Marketplace Patents on Thiocolchicoside
Experimental / Informatics
List of terms related to Thiocolchicoside

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Thiocolchicoside (Muscoril, Myoril, Neoflax) is a muscle relaxant with anti-inflammatory and analgesic effects.^[3]^[4]^[5]^[6] It acts as a competitive GABA_A receptor antagonist and also glycine receptor antagonist with similar potency and nicotinic acetylcholine receptors to a much lesser extent.^[7]^[8] It has powerful convulsant activity and should not be used in seizure-prone individuals.^[9]^[10]^[11]

Side effects

Side effect of thiocolchicoside can include nausea, somnolence, allergy and vasovagal reactions.^[12]

Although Musle relaxant have major side effect of Sedation, but Thiocholchicoside is free from sedation effect possible due to non-interference with nicotinic receptors.^{[citation needed]}

Pharmacokinetics

Thiocolchicoside is broken down in the body to a metabolite called 3-demethylthiocolchicine (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.^{[citation needed]} Therefore recommended oral dose should not exceed 7 days and intramuscular dose duration should not exceed 5 days.Template:Medcn Local skin preparations are less toxic.

References

↑ ^1.0 ^1.1 Perucca E, Poitou P, Pifferi G (1995). "Comparative pharmacokinetics and bioavailability of two oral formulations of thiocolchicoside, a GABA-mimetic muscle relaxant drug, in normal volunteers". European Journal of Drug Metabolism and Pharmacokinetics. 20 (4): 301–5. doi:10.1007/bf03190249. PMID 8983937.
↑ Sandouk P, Bouvier d'Yvoire M, Chretien P, Tillement JP, Scherrmann JM (January 1994). "Single-dose bioavailability of oral and intramuscular thiocolchicoside in healthy volunteers". Biopharmaceutics & Drug Disposition. 15 (1): 87–92. doi:10.1002/bdd.2510150108. PMID 8161719.
↑ Tüzün F, Unalan H, Oner N; et al. (September 2003). "Multicenter, randomized, double-blinded, placebo-controlled trial of thiocolchicoside in acute low back pain". Joint, Bone, Spine : Revue Du Rhumatisme. 70 (5): 356–61. doi:10.1016/S1297-319X(03)00075-7. PMID 14563464.
↑ Ketenci A, Basat H, Esmaeilzadeh S (July 2009). "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 of the Turkish Society of Algology. 21 (3): 95–103. PMID 19780000.
↑ Soonawalla DF, Joshi N (May 2008). "Efficacy of thiocolchicoside in Indian patients suffering from low back pain associated with muscle spasm". Journal of the Indian Medical Association. 106 (5): 331–5. PMID 18839644.
↑ Ketenci A, Ozcan E, Karamursel S (July 2005). "Assessment of efficacy and psychomotor performances of thiocolchicoside and tizanidine in patients with acute low back pain". International Journal of Clinical Practice. 59 (7): 764–70. doi:10.1111/j.1742-1241.2004.00454.x. PMID 15963201.
↑ Carta M, Murru L, Botta P; et al. (September 2006). "The muscle relaxant thiocolchicoside is an agonist of GABAA receptor function in the central nervous system". Neuropharmacology. 51 (4): 805–15. doi:10.1016/j.neuropharm.2006.05.023. PMID 16806306.
↑ Mascia MP, Bachis E, Obili N; et al. (March 2007). "Thiocolchicoside inhibits the activity of various subtypes of recombinant GABA(A) receptors expressed in Xenopus laevis oocytes". European Journal of Pharmacology. 558 (1–3): 37–42. doi:10.1016/j.ejphar.2006.11.076. PMID 17234181.
↑ De Riu PL, Rosati G, Sotgiu S, Sechi G (August 2001). "Epileptic seizures after treatment with thiocolchicoside". Epilepsia. 42 (8): 1084–6. doi:10.1046/j.1528-1157.2001.0420081084.x. PMID 11554898.
↑ Giavina-Bianchi P, Giavina-Bianchi M, Tanno LK, Ensina LF, Motta AA, Kalil J (June 2009). "Epileptic seizure after treatment with thiocolchicoside". Therapeutics and Clinical Risk Management. 5 (3): 635–7. doi:10.2147/tcrm.s4823. PMC 2731019. PMID 19707540.
↑ Sechi G, De Riu P, Mameli O, Deiana GA, Cocco GA, Rosati G (October 2003). "Focal and secondarily generalised convulsive status epilepticus induced by thiocolchicoside in the rat". Seizure : the Journal of the British Epilepsy Association. 12 (7): 508–15. doi:10.1016/S1059-1311(03)00053-0. PMID 12967581.
↑ "Thiocolchicoside-induced liver injury". Mar 2011. Retrieved Dec 2014. Check date values in: |accessdate= (help)

Template:Anti-inflammatory

[pmid8983937-1] 1.0 ^1.1 Perucca E, Poitou P, Pifferi G (1995). "Comparative pharmacokinetics and bioavailability of two oral formulations of thiocolchicoside, a GABA-mimetic muscle relaxant drug, in normal volunteers". European Journal of Drug Metabolism and Pharmacokinetics. 20 (4): 301–5. doi:10.1007/bf03190249. PMID 8983937.

[pmid8161719-2] Sandouk P, Bouvier d'Yvoire M, Chretien P, Tillement JP, Scherrmann JM (January 1994). "Single-dose bioavailability of oral and intramuscular thiocolchicoside in healthy volunteers". Biopharmaceutics & Drug Disposition. 15 (1): 87–92. doi:10.1002/bdd.2510150108. PMID 8161719.

[pmid14563464-3] Tüzün F, Unalan H, Oner N; et al. (September 2003). "Multicenter, randomized, double-blinded, placebo-controlled trial of thiocolchicoside in acute low back pain". Joint, Bone, Spine : Revue Du Rhumatisme. 70 (5): 356–61. doi:10.1016/S1297-319X(03)00075-7. PMID 14563464.

[pmid19780000-4] Ketenci A, Basat H, Esmaeilzadeh S (July 2009). "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 of the Turkish Society of Algology. 21 (3): 95–103. PMID 19780000.

[pmid18839644-5] Soonawalla DF, Joshi N (May 2008). "Efficacy of thiocolchicoside in Indian patients suffering from low back pain associated with muscle spasm". Journal of the Indian Medical Association. 106 (5): 331–5. PMID 18839644.

[pmid15963201-6] Ketenci A, Ozcan E, Karamursel S (July 2005). "Assessment of efficacy and psychomotor performances of thiocolchicoside and tizanidine in patients with acute low back pain". International Journal of Clinical Practice. 59 (7): 764–70. doi:10.1111/j.1742-1241.2004.00454.x. PMID 15963201.

[pmid16806306-7] Carta M, Murru L, Botta P; et al. (September 2006). "The muscle relaxant thiocolchicoside is an agonist of GABAA receptor function in the central nervous system". Neuropharmacology. 51 (4): 805–15. doi:10.1016/j.neuropharm.2006.05.023. PMID 16806306.

[pmid17234181-8] Mascia MP, Bachis E, Obili N; et al. (March 2007). "Thiocolchicoside inhibits the activity of various subtypes of recombinant GABA(A) receptors expressed in Xenopus laevis oocytes". European Journal of Pharmacology. 558 (1–3): 37–42. doi:10.1016/j.ejphar.2006.11.076. PMID 17234181.

[pmid11554898-9] De Riu PL, Rosati G, Sotgiu S, Sechi G (August 2001). "Epileptic seizures after treatment with thiocolchicoside". Epilepsia. 42 (8): 1084–6. doi:10.1046/j.1528-1157.2001.0420081084.x. PMID 11554898.

[pmid19707540-10] Giavina-Bianchi P, Giavina-Bianchi M, Tanno LK, Ensina LF, Motta AA, Kalil J (June 2009). "Epileptic seizure after treatment with thiocolchicoside". Therapeutics and Clinical Risk Management. 5 (3): 635–7. doi:10.2147/tcrm.s4823. PMC 2731019. PMID 19707540.

[pmid12967581-11] Sechi G, De Riu P, Mameli O, Deiana GA, Cocco GA, Rosati G (October 2003). "Focal and secondarily generalised convulsive status epilepticus induced by thiocolchicoside in the rat". Seizure : the Journal of the British Epilepsy Association. 12 (7): 508–15. doi:10.1016/S1059-1311(03)00053-0. PMID 12967581.

[12] "Thiocolchicoside-induced liver injury". Mar 2011. Retrieved Dec 2014. Check date values in: |accessdate= (help)

[1]

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[3]

[4]

[5]

[6]

[7]

[8]

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[12]

@@ Line 28: / Line 28: @@
+{{Drugbox
+| Verifiedfields = changed
+| Watchedfields = changed
+| verifiedrevid = 448013724
+| IUPAC_name = ''N''-[(7''S'')-3-(β-<small>D</small>-Glucopyranosyloxy)-1,2-dimethoxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[''a'']heptalen-7-yl]acetamide
+| image = Thiocolchicoside.png
+<!--Clinical data-->
+| tradename =
+| Drugs.com = {{drugs.com|international|thiocolchicoside}}
+| legal_status = Rx-only
+| routes_of_administration = [[oral administration|Oral]], [[Topical]], [[Intramuscular|IM]]
+<!--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 = 10.1007/bf03190249| url = }}</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 |date=January 1994 | pmid = 8161719 | doi = 10.1002/bdd.2510150108| url = }}</ref>
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 602-41-5
+| ATC_prefix = M03
+| ATC_suffix = BX05
+| PubChem = 72067
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 1705373
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = T1X8S697GT
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D07276
+<!--Chemical data-->
+| C=27 | H=33 | N=1 | O=10 | S=1
+| molecular_weight = 563.618 g/mol
+| smiles = O=C(N[C@@H]4C1=C\C(=O)C(/SC)=C\C=C1c3c(cc(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]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-/m1/s1
+| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChIKey = LEQAKWQJCITZNK-MSQQGMGVSA-N
+}}
+__Notoc__
+{{SI}}
+{{CMG}}
 ==Overview==
-'''Thiocolchicoside''' is a [[muscle relaxant]].
+'''Thiocolchicoside''' ('''Muscoril''', '''Myoril''', '''Neoflax''') is a [[muscle relaxant]] with [[anti-inflammatory]] and [[analgesic]] 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 |date=September 2003 | pmid = 14563464 | doi = 10.1016/S1297-319X(03)00075-7| 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 |date=July 2009 | 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 |date=May 2008 | 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 |date=July 2005 | 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 [[competitive inhibition|competitive]] [[GABAA receptor|GABA<sub>A</sub> receptor]] [[receptor antagonist|antagonist]] and also [[glycine receptor]] antagonist with similar [[potency (pharmacology)|potency]] and [[nicotinic acetylcholine receptor]]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 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 | 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 |date=March 2007 | 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 [[convulsant]] activity and should not be used in [[seizure]]-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 |date=August 2001 | 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 |date=June 2009 | pmid = 19707540 | pmc = 2731019 | doi = 10.2147/tcrm.s4823| 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 |date=October 2003 | pmid = 12967581 | doi = 10.1016/S1059-1311(03)00053-0| url = http://linkinghub.elsevier.com/retrieve/pii/S1059131103000530}}</ref>
-{{Muscle relaxants}}
+== Side effects ==
+Side effect of thiocolchicoside can include nausea, somnolence, allergy and vasovagal reactions.<ref>{{Cite web|url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3072020/|title = Thiocolchicoside-induced liver injury|date = Mar 2011|accessdate = Dec 2014|website = |publisher = |last = |first = }}</ref>
+Although Musle relaxant have major side effect of Sedation, but Thiocholchicoside is free from sedation effect possible due to non-interference with nicotinic receptors.{{Citation needed|date = December 2014}}
+==Pharmacokinetics==
+Thiocolchicoside is broken down in the body to a [[metabolite]] called [[3-demethylthiocolchicine]] (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.{{citation needed|date=November 2013}} Therefore recommended oral dose should not exceed 7 days and intramuscular dose duration should not exceed 5 days.{{medcn|date=February 2014}}  Local skin preparations are less toxic.
-[[Category:Glycosides]]
+==References==
+{{Reflist|2}}
-{{WikiDoc Sources}}
+{{Muscle relaxants}}
+{{Analgesics}}
+{{Anti-inflammatory}}
+{{GABAergics}}
+{{Glycinergics}}
+{{Cholinergics}}
-{{WH}}
+[[Category:Glucosides]]
+[[Category:Phenol ethers]]
+[[Category:Acetamides]]
+[[Category:Tropones]]
+[[Category:Heptalenes]]
+[[Category:Thioethers]]
+[[Category:Glycine receptor antagonists]]
+[[Category:GABAA receptor antagonists]]
+[[Category:Nicotinic antagonists]]

v t e Skeletal Muscle relaxants (M03)
Peripherally acting (primarily antinicotinic, neuromuscular-blocking drugs)	Template:Navbox subgroup
Centrally Acting	Template:Navbox subgroup
Directly acting	Dantrolene

v t e Analgesic products (N02A, N02B)
Opioids See also: Opioids template	Alphaprodine · Anileridine · Buprenorphine · Butorphanol · Codeine · Dextromoramide · Dextropropoxyphene · Dezocine · Desomorphine · Diamorphine · Dihydrocodeine · Dihydromorphine · Fentanyl · Hydrocodone · Hydromorphone · Ketobemidone · Levorphanol · Meptazinol · Methadone · Morphine · Nalbuphine · Nicomorphine · Opium · Oxycodone · Oxymorphone · Pethidine · Pentazocine · Pethidine · Piminodine · Piritramide · Tilidine · Tramadol · Tapentadol
Salicylic acid and derivatives	Aspirin (Acetylsalicylic Acid) · Benorylate · Diflunisal · Ethenzamide · Magnesium Salicylate · Salicin · Salicylamide · Salsalate · See also: NSAIDs
Pyrazolones	Ampyrone/Aminophenazone · Metamizole · Phenazone
Cannabinoids	Cannabis · Tetrahydrocannabinol · AM404
Anilides	Paracetamol (acetaminophen) · Phenacetin · Propacetamol
Non-Salicylate Non-Steroidal Anti-Inflammatories See also: NSAIDs template	Template:Navbox subgroup
Atypical, Adjunct & Miscellaneous	Bicifadine · Clonidine · Cyclobenzaprine · Duloxetine · Flupirtine · Gabapentin · Nefopam · Orphenadrine · Trazadone · Ziconotide

Clinical data
ATC code	M03BX05 (WHO)
Identifiers
IUPAC name N-[1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-benzo[d]heptalen-7-yl]acetamide
PubChem CID	72067
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
Formula	C₂₇H₃₃NO₁₀S
Molar mass	563.618 g/mol

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, Topical, IM
ATC code	M03BX05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	25%^[1]
Elimination half-life	5-6 hours^[1]^[2]
Identifiers
IUPAC name N-[(7S)-3-(β-D-Glucopyranosyloxy)-1,2-dimethoxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
CAS Number	602-41-5^Y
PubChem CID	72067
UNII	T1X8S697GT
KEGG	D07276^Y
ChEMBL	ChEMBL1705373^N
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
Formula	C₂₇H₃₃NO₁₀S
Molar mass	563.618 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(N[C@@H]4C1=C\C(=O)C(/SC)=C\C=C1c3c(cc(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)c(OC)c3OC)CC4)C
InChI InChI=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-/m1/s1^N Key:LEQAKWQJCITZNK-MSQQGMGVSA-N^N
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