THIOCOLCHICOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H33NO10S
Molecular Weight	563.617
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C2=C(CC[C@H](NC(C)=O)C3=CC(=O)C(SC)=CC=C23)C=C1O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

InChI

InChIKey=LEQAKWQJCITZNK-AXHKHJLKSA-N

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+/m0/s1

HIDE SMILES / InChI

Description
Sources: http://www.ema.europa.eu/ema/index.jsp?curl=pages/news_and_events/news/2013/11/news_detail_001967.jsp&mid=WC0b01ac058004d5c1 | https://www.drugbank.ca/drugs/DB11582 | http://plaintips.com/muscoril | https://www.ncbi.nlm.nih.gov/pubmed/16806306

Thiocolchicoside is a muscle relaxant that has been authorised by national procedures in several EU Member States for use by mouth or injection into the muscles in the treatment of painful muscular disorders. Thiocolchicoside is marketed under the brand name Muscoril among others. Thiocolchicoside (TCC) is used clinically for its muscle relaxant, anti-inflammatory, and analgesic properties, and it has been shown to interact with gamma-aminobutyric acid (GABA) type A receptors (GABAARs) and strychnine-sensitive glycine receptors in the rat central nervous system.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucose-6-phosphate 1-dehydrogenase 12 Target ID: CHEMBL5347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21054237	Inhibitor 8297		0.056 mM [IC50]
GABA-A receptor; anion channel 202 Target ID: CHEMBL1907607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16806306 \| https://www.ncbi.nlm.nih.gov/pubmed/10440100 \| https://www.ncbi.nlm.nih.gov/pubmed/6274664	Antagonist 2778		1.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Painful muscle contractures in acute spinal pathology 1 Sources: http://products.sanofi.com.pk/Muscoril_HCP_Guide.pdf http://products.sanofi.com.pk/Muscoril_HCP_Guide.pdf http://www.ema.europa.eu/docs/en_GB/document_library/Press_release/2013/11/WC500155448.pdf	Palliative		Approved 8429	Muscoril Approved Use Muscoril capsules and injections are used as an adjuvant treatment of painful muscle contractures in acute spinal pathology.

PubMed

Title	Date	PubMed
Epileptic seizures after treatment with thiocolchicoside.	2001 Aug	11554898
Photosensitizing activity of thiocolchicoside: photochemical and in vitro phototoxicity studies.	2001 Jan	11210677
Autoradiographic localization of [3H]thiocolchicoside binding sites in the rat brain and spinal cord.	2001 Jun	11406196
Comparative bioavailability and tolerability study of two intramuscular formulations of thiocolchicoside in healthy volunteers.	2001 Oct-Dec	11808868
Highly specific and sensitive liquid chromatography-tandem mass spectrometry method for the determination of 3-desmethylthiocolchicine in human plasma as analyte for the assessment of bioequivalence after oral administration of thiocolchicoside.	2002 Mar 8	11999759
Vehicle effects on in vitro skin permeation of thiocolchicoside.	2002 Nov	12611278
Physicochemical compatibility between thiocolchicoside injections (Miotens) and pharmaceutical products frequently used for combined therapy.	2002 Nov	12484541
In vitro permeation screening of a new formulation of thiocolchicoside containing various enhancers.	2002 Oct-Dec	12511205
Buccal delivery of thiocolchicoside: in vitro and in vivo permeation studies.	2003 Jan 2	12480286
Determination of thiocolchicoside in its binary mixtures (thiocolchicoside-glafenine and thiocolchicoside-floctafenine) by TLC-densitometry.	2003 Jun	12767387
Focal and secondarily generalised convulsive status epilepticus induced by thiocolchicoside in the rat.	2003 Oct	12967581
Multicenter, randomized, double-blinded, placebo-controlled trial of thiocolchicoside in acute low back pain.	2003 Sep	14563464
New metabolic and pharmacokinetic characteristics of thiocolchicoside and its active metabolite in healthy humans.	2004 Aug	15312157
Effect of chemical enhancers and iontophoresis on thiocolchicoside permeation across rabbit and human skin in vitro.	2004 Oct	15349953
Treatment of refractory seizures due to a benign mass present in the corpus callosum with an ion magnetic inductor: case report.	2005	18095111
Assessment of efficacy and psychomotor performances of thiocolchicoside and tizanidine in patients with acute low back pain.	2005 Jul	15963201
Skin atrophy caused by thiocolchicoside injections.	2006 Dec	17184273
Ultraviolet absorbance detection of colchicine and related alkaloids on a capillary electrophoresis microchip.	2006 Jul 21	17723479
The muscle relaxant thiocolchicoside is an antagonist of GABAA receptor function in the central nervous system.	2006 Sep	16806306
A placebo-controlled comparison of the efficiency of triple- and monotherapy in category III B chronic pelvic pain syndrome (CPPS).	2007 Apr	17084960
Thiocolchicoside inhibits the activity of various subtypes of recombinant GABA(A) receptors expressed in Xenopus laevis oocytes.	2007 Mar 8	17234181
Novel 3-O-glycosyl-3-demethylthiocolchicines as ligands for glycine and gamma-aminobutyric acid receptors.	2007 May 3	17411024
UV-Vis spectrophotometrical and analytical methodology for the determination of singlet oxygen in new antibacterials drugs.	2007 Nov 11	19662185
Penetration and distribution of thiocolchicoside through human skin: comparison between a commercial foam (Miotens) and a drug solution.	2008	19051040
Embolia cutis medicamentosa following thiocolchicoside injection.	2008 Aug	18070022
Efficacy and safety of eperisone in patients with low back pain: a double blind randomized study.	2008 Jul-Aug	18727454
Efficacy of thiocolchicoside in Indian patients suffering from low back pain associated with muscle spasm.	2008 May	18839644
Effect of interlaminar epidural steroid injection in acute and subacute pain due to lumbar disk herniation: a randomized comparison of 2 different protocols.	2009 Dec 24	20111695
The efficacy of topical thiocolchicoside (Muscoril) in the treatment of acute cervical myofascial pain syndrome: a single-blind, randomized, prospective, phase IV clinical study.	2009 Jul	19780000
Epileptic seizure after treatment with thiocolchicoside.	2009 Jun	19707540
[A rare cause of cyanosis: Sulphaemoglobinaemia related to thiocolchicoside (Miorel)].	2010	20146957
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Effects of some drugs on human erythrocyte glucose 6-phosphate dehydrogenase: an in vitro study.	2010 Dec	21054237
High-performance thin-layer chromatographic determination of etoricoxib and thiocolchicoside in combined tablet dosage form.	2010 May-Jun	20629376
Thiocolchicoside exhibits anticancer effects through downregulation of NF-κB pathway and its regulated gene products linked to inflammation and cancer.	2010 Nov	20978115
[Usefulness of botulinum toxin injections in the treatment of postoperative pain after cervical spine surgery: Preliminary results].	2010 Oct	20870255

Patents

Sample Use Guides

In Vivo Use Guide

For oral use: The recommended and maximal dose of Muscoril (Thiocolchicoside) is 8 mg every 12 hours (i.e. 16 mg per day). The treatment duration is limited to 7 consecutive days. For IM use: The recommended and maximal dose of Muscoril Injection is 4 mg every 12 hours (i.e. 8 mg per day). The treatment duration is limited to 5 consecutive days.

Route of Administration: Other

In Vitro Use Guide

The phasic and tonic GABAAR-mediated currents recorded from Purkinje cells and granule neurons, respectively, in parasagittal cerebellar slices from adult male rats were inhibited by Thiocolchicoside in a concentration-dependent manner. The median inhibitory concentrations of Thiocolchicoside for these effects were approximately 0.15 and approximately 0.9 uM, respectively.

Name

Type

Language

THIOCOLCHICOSIDE

Official Name

English

thiocolchicoside [INN]

Common Name

English

Thiocolchicoside [WHO-DD]

Common Name

English

NSC-147755

Code

English

THIOCOLCHICOSIDE [MART.]

Common Name

English

2-10-DI(DEMETHOXY)-2-GLUCOSYLOXY-10-METHYLTHIOCOLCHICINE

Common Name

English

THIOCOLCHICINE 2-GLUCOSIDE ANALOG

Common Name

English

COLTRAMYL

Brand Name

English

COLTRAX

Brand Name

English

THIOCOLCHICINE 2-GLUCOSIDE ANALOG [MI]

Common Name

English

MIOREL

Brand Name

English

MUSCO-RIL

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QM03BX05