Structure via PubChem · Public domain (PubChem)
(RS)-thiocolchicoside
Sign in to saveAlso known as N-[1,2-dimethoxy-10-(methylthio)-9-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy}-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide, thiocolchicoside
Thiocolchicoside (Muscoril, Myoril, Neoflax) is a semi-synthetic derivative of colchicine, used as muscle relaxant with anti-inflammatory and analgesic effects. Its mechanism of action is unknown, but it is believed to act via antagonism of nicotinic acetylcholine receptors (nAchRs). However, it also appears to be a competitive antagonist of GABAA and glycine receptors. As such, it has powerful convulsant activity and should not be used in seizure-prone individuals.
Chemical data
- Formula
- C27H33NO10S
- Molecular weight
- 563.6 g/mol
- 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[a]heptalen-7-yl]acetamide
- SMILES
- CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)SC)OC)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
- InChIKey
- LEQAKWQJCITZNK-MSQQGMGVSA-N
- XLogP
- -0.4
- Polar surface area
- 189 Ų
- H-bond donors
- 5
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 563.183
Show 4 more facts
- chemical formula
- C₂₇H₃₃NO₁₀S
- canonical SMILES
- CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)SC)OC)OC)OC4C(C(C(C(O4)CO)O)O)O
- isomeric SMILES
- CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)SC)OC)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
- Commons category
- Thiocolchicoside
Sources (1)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Medical uses
- Low back pain
- Side effects
- Pharmacokinetics
- References
Thiocolchicoside (Muscoril, Myoril, Neoflax) is a semi-synthetic derivative of colchicine, used as muscle relaxant with anti-inflammatory and analgesic effects. Its mechanism of action is unknown, but it is believed to act via antagonism of nicotinic acetylcholine receptors (nAchRs). However, it also appears to be a competitive antagonist of GABAA and glycine receptors. As such, it has powerful convulsant activity and should not be used in seizure-prone individuals.
== 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 paracetamol. 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.
Excerpted from Wikipedia’s “(RS)-thiocolchicoside” article, available under the CC BY-SA 4.0 licence.