A GABAA receptor antagonist
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Thiocolchicoside

Item No. 35821

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(7S)-3-(β-D-glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2-dimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]-acetamide
CAS Number
602-41-5
Synonyms
  • NSC 147755
  • R-271
Molecular Formula
C27H33NO10S
Formula Weight
563.6
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 5 mg/mlEthanol: insolPBS (pH 7.2): 5 mg/ml
λmax
257, 291, 382 nm
SMILES
COC1=C2C(C([C@H](CCC2=CC(O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO)=C1OC)NC(C)=O)=C4)=CC=C(SC)C4=O
InChi Code
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
InChi Key
LEQAKWQJCITZNK-AXHKHJLKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    Product Description

    Thiocolchicoside is a GABAA receptor antagonist.1 It inhibits GABAA receptor-mediated currents in Purkinje cells isolated from rat cerebellum (IC50 = 0.15 µM). It binds strychnine-sensitive glycine receptors in isolated rat spinal cord (IC50 = 1.58 µM).2 Thiocolchicoside inhibits cell growth in a panel of cancer cell lines, including KBM5 leukemia and U266 myeloma cells, SCC4 squamous cell carcinoma cells, and HCT116 colon, MCF-7 breast, and A293 kidney cancer cells when used at concentrations ranging from 25 to 100 µM.3 It inhibits the anti-apoptotic proteins Bcl-2, X-linked inhibitor of apoptosis (XIAP), myeloid cell leukemia-1 (Mcl-1), Bcl-xL, cIAP-1, and cIAP-2 in KBM5 cells in a concentration-dependent manner. It also inhibits TNF-α-induced NF-κB activation and IκBα degradation in KBM5 cells in a concentration-dependent manner. Formulations containing thiocolchicoside have been used as muscle relaxers in the treatment of rheumatoid arthritis, joint stiffness, and muscle stiffness.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Carta, M., Murru, L., Botta, P., et al. The muscle relaxant thiocolchicoside is an antagonist of GABAA receptor function in the central nervous system. Neuropharmacology 51(4), 805-815 (2006).

    2. Cimino, M., Marini, P., and Cattabeni, F. Interaction of thiocolchicoside with [3H]strychnine binding sites in rat x spinal cord and brainstem. Eur. J. Pharmacol. 318(1), 201-204 (1996).

    3. Reuter, S., Prasad, S., Phromnoi, K., et al. Thiocolchicoside exhibits anticancer effects through downregulation of NF-κB pathway and its regulated gene products linked to inflammation and cancer. Cancer Prev. Res. (Phila) 3(11), 1462-1472 (2010).