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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(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

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 TargetPharmacologyConditionPotency
0.056 mM [IC50]
1.9 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Muscoril

Cmax

ValueDoseCo-administeredAnalytePopulation
61 ng/mL
8 mg single, oral
(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
11.7 ng/mL
8 mg single, intramuscular
(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
174.8 ng/mL
8 mg single, intramuscular
THIOCOLCHICOSIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
126 ng × h/mL
8 mg single, oral
(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
83 ng × h/mL
8 mg single, intramuscular
(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
417 ng × h/mL
8 mg single, intramuscular
THIOCOLCHICOSIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.3 h
8 mg single, oral
(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
8.6 h
8 mg single, intramuscular
(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
1.5 h
8 mg single, intramuscular
THIOCOLCHICOSIDE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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.