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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 of THIOCOLCHICOSIDE

SMILES

COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C3CC[C@H](NC(C)=O)C4=CC(=O)C(SC)=CC=C4C3=C1OC

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
Molecular Formula C27H33NO10S
Molecular Weight 563.617
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

CNS Active
4002
Curator's Comment: Intraperitoneal injection of Thiocolchicoside in rats either alone or in combination with negative modulators of GABAergic transmission revealed convulsant and proconvulsant actions of this drug.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.056 mM [IC50]
Antagonist
2849
 1.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
Muscoril

Approved Use

Muscoril capsules and injections are used as an adjuvant treatment of painful muscle contractures in acute spinal pathology.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
61 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
(7S)-7-(ACETYLAMINO)-5,6,7,9-TETRAHYDRO-1,2-DIMETHOXY-10-(METHYLTHIO)-9-OXOBENZO(A)HEPTALEN-3-YL BETA-D-GLUCOPYRANOSIDURONIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
11.7 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, intramuscular
dose: 8 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
(7S)-7-(ACETYLAMINO)-5,6,7,9-TETRAHYDRO-1,2-DIMETHOXY-10-(METHYLTHIO)-9-OXOBENZO(A)HEPTALEN-3-YL BETA-D-GLUCOPYRANOSIDURONIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
174.8 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, intramuscular
dose: 8 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIOCOLCHICOSIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
126 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
(7S)-7-(ACETYLAMINO)-5,6,7,9-TETRAHYDRO-1,2-DIMETHOXY-10-(METHYLTHIO)-9-OXOBENZO(A)HEPTALEN-3-YL BETA-D-GLUCOPYRANOSIDURONIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
83 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, intramuscular
dose: 8 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
(7S)-7-(ACETYLAMINO)-5,6,7,9-TETRAHYDRO-1,2-DIMETHOXY-10-(METHYLTHIO)-9-OXOBENZO(A)HEPTALEN-3-YL BETA-D-GLUCOPYRANOSIDURONIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
417 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, intramuscular
dose: 8 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIOCOLCHICOSIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
(7S)-7-(ACETYLAMINO)-5,6,7,9-TETRAHYDRO-1,2-DIMETHOXY-10-(METHYLTHIO)-9-OXOBENZO(A)HEPTALEN-3-YL BETA-D-GLUCOPYRANOSIDURONIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, intramuscular
dose: 8 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
(7S)-7-(ACETYLAMINO)-5,6,7,9-TETRAHYDRO-1,2-DIMETHOXY-10-(METHYLTHIO)-9-OXOBENZO(A)HEPTALEN-3-YL BETA-D-GLUCOPYRANOSIDURONIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15312157/
8 mg single, intramuscular
dose: 8 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIOCOLCHICOSIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.25 % 3 times / day multiple, topical
Studied dose
Dose: 0.25 %, 3 times / day
Route: topical
Route: multiple
Dose: 0.25 %, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/36589351/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/36589351/
Disc. AE: Application site pain...
AEs leading to
discontinuation/dose reduction:
Application site pain
Sources:
https://pubmed.ncbi.nlm.nih.gov/36589351/
AEs

AEs

AESignificanceDosePopulation
Application site pain Disc. AE
0.25 % 3 times / day multiple, topical
Studied dose
Dose: 0.25 %, 3 times / day
Route: topical
Route: multiple
Dose: 0.25 %, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/36589351/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/36589351/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
1087
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP19A1
429

BSEP
550
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BSEP
554
 no [IC50 >133 uM]
CYP19A1
430
 no
CYP3A4
2633
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010-12
Effects of some drugs on human erythrocyte glucose 6-phosphate dehydrogenase: an in vitro study.
2010-12
Thiocolchicoside exhibits anticancer effects through downregulation of NF-κB pathway and its regulated gene products linked to inflammation and cancer.
2010-11
[Usefulness of botulinum toxin injections in the treatment of postoperative pain after cervical spine surgery: Preliminary results].
2010-10
High-performance thin-layer chromatographic determination of etoricoxib and thiocolchicoside in combined tablet dosage form.
2010-07-16
[A rare cause of cyanosis: Sulphaemoglobinaemia related to thiocolchicoside (Miorel)].
2010
Effect of interlaminar epidural steroid injection in acute and subacute pain due to lumbar disk herniation: a randomized comparison of 2 different protocols.
2009-12-24
The efficacy of topical thiocolchicoside (Muscoril) in the treatment of acute cervical myofascial pain syndrome: a single-blind, randomized, prospective, phase IV clinical study.
2009-07
Epileptic seizure after treatment with thiocolchicoside.
2009-06
Efficacy and safety of eperisone in patients with low back pain: a double blind randomized study.
2008-08-30
Embolia cutis medicamentosa following thiocolchicoside injection.
2008-08
Efficacy of thiocolchicoside in Indian patients suffering from low back pain associated with muscle spasm.
2008-05
Penetration and distribution of thiocolchicoside through human skin: comparison between a commercial foam (Miotens) and a drug solution.
2008
UV-Vis spectrophotometrical and analytical methodology for the determination of singlet oxygen in new antibacterials drugs.
2007-11-11
Novel 3-O-glycosyl-3-demethylthiocolchicines as ligands for glycine and gamma-aminobutyric acid receptors.
2007-05-03
A placebo-controlled comparison of the efficiency of triple- and monotherapy in category III B chronic pelvic pain syndrome (CPPS).
2007-04
Thiocolchicoside inhibits the activity of various subtypes of recombinant GABA(A) receptors expressed in Xenopus laevis oocytes.
2007-03-08
Skin atrophy caused by thiocolchicoside injections.
2006-12
The muscle relaxant thiocolchicoside is an antagonist of GABAA receptor function in the central nervous system.
2006-09
Ultraviolet absorbance detection of colchicine and related alkaloids on a capillary electrophoresis microchip.
2006-07-21
Assessment of efficacy and psychomotor performances of thiocolchicoside and tizanidine in patients with acute low back pain.
2005-07
Treatment of refractory seizures due to a benign mass present in the corpus callosum with an ion magnetic inductor: case report.
2005
Effect of chemical enhancers and iontophoresis on thiocolchicoside permeation across rabbit and human skin in vitro.
2004-10
New metabolic and pharmacokinetic characteristics of thiocolchicoside and its active metabolite in healthy humans.
2004-08
Focal and secondarily generalised convulsive status epilepticus induced by thiocolchicoside in the rat.
2003-10
Multicenter, randomized, double-blinded, placebo-controlled trial of thiocolchicoside in acute low back pain.
2003-09
Determination of thiocolchicoside in its binary mixtures (thiocolchicoside-glafenine and thiocolchicoside-floctafenine) by TLC-densitometry.
2003-06
In vitro permeation screening of a new formulation of thiocolchicoside containing various enhancers.
2003-01-04
Buccal delivery of thiocolchicoside: in vitro and in vivo permeation studies.
2003-01-02
Vehicle effects on in vitro skin permeation of thiocolchicoside.
2002-11
Physicochemical compatibility between thiocolchicoside injections (Miotens) and pharmaceutical products frequently used for combined therapy.
2002-11
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.
2002-03-08
Comparative bioavailability and tolerability study of two intramuscular formulations of thiocolchicoside in healthy volunteers.
2002-01-26
Epileptic seizures after treatment with thiocolchicoside.
2001-08
Autoradiographic localization of [3H]thiocolchicoside binding sites in the rat brain and spinal cord.
2001-06
Photosensitizing activity of thiocolchicoside: photochemical and in vitro phototoxicity studies.
2001-01
Patents

Patents

WO2010120253A1
1
WO2011112161A1
1

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:47:47 GMT 2025
Edited
by admin
on Mon Mar 31 18:47:47 GMT 2025
Record UNII
T1X8S697GT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIOCOLCHICOSIDE
INN   MART.   WHO-DD  
INN  
Official Name English
COLTRAMYL
Preferred 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
MI  
Common 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
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
WHO-ATC M03BX05
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
NCI_THESAURUS C29696
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
WHO-ATC M03BX55
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
Code System Code Type Description
SMS_ID
100000091997
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
RXCUI
38085
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY RxNorm
INN
671
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
NCI_THESAURUS
C152589
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
WIKIPEDIA
Thiocolchicoside
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
DRUG CENTRAL
4731
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID5045330
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
DRUG BANK
DB11582
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
EVMPD
SUB10976MIG
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
MESH
C004280
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
FDA UNII
T1X8S697GT
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
NSC
147755
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
PUBCHEM
9915886
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
CAS
602-41-5
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
210-017-7
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
MERCK INDEX
m10747
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1705373
Created by admin on Mon Mar 31 18:47:47 GMT 2025 , Edited by admin on Mon Mar 31 18:47:47 GMT 2025
PRIMARY
Related Record Type Details
Structure of (7S)-7-(ACETYLAMINO)-5,6,7,9-TETRAHYDRO-1,2-DIMETHOXY-10-(METHYLTHIO)-9-OXOBENZO(A)HEPTALEN-3-YL .BETA.-D-GLUCOPYRANOSIDURONIC ACID
METABOLITE ACTIVE -> PARENT
Structure of 3-DESMETHYLTHIOCOLCHICINE
METABOLITE -> PARENT
Related Record Type Details
Structure of THIOCOLCHICOSIDE
ACTIVE MOIETY
NIH
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