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Chemical Structure
Chemical Structure
Chemical Structure

Colchicine [64-86-8]

Research Use Only
AG-CN2-0048
AdipoGen Life Sciences
CAS Number64-86-8
Product group Chemicals
Estimated Purity>97%
Molecular Weight399.4
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Colchicine
  • Delivery Days Customer
    10
  • ADR Class
    6.1
  • CAS Number
    64-86-8
  • Certification
    Research Use Only
  • Estimated Purity
    >97%
  • Hazard Information
    Danger,Excepted quantity
  • Molecular Formula
    C22H25NO6
  • Molecular Weight
    399.4
  • Scientific Description
    Anti-cancer compound [5]. Microtubule assembly inhibitor. Depolymerizes microtubules and limits microtubule formation (inactivates spindle fibre formation) [1, 2, 5, 6]. Inhibits mitosis during cell division at metaphase by inhibiting spindle formation [6]. Anti-inflammatory compound [7, 9]. Suppresses monosodium urate crystal-induced NLRP3/NALP3 inflammasome-driven caspase-1 activation, IL-1beta processing and release, and L-selectin expression on neutrophils at micromolar concentrations. Blocks the release of a crystal-derived chemotactic factor from neutrophil lysosomes, blocks neutrophil adhesion to, and inhibits monosodium urate crystal-induced production of superoxide anions from neutrophils at nanomolar concentrations [7]. Drug used in treatment of gout, familial Mediterranean fever, pericarditis and Behects disease. Investigated for its anti-cancer activity [5, 8, 9]. It has a narrow therapeutic index with no clear-cut distinction between nontoxic, toxic and lethal doses, causing substantial confusion among clinicians [8]. Apoptosis inducer in a variety of normal and tumor cell lines [3, 4]. Inhibitor of autophagosome-lysosome fusion. Inhibits acetylated a-tubulin mediated dynein dependent transport of mitochondria and subsequent apposition of ASC on mitochondria to NLRP3 on the endoplasmic reticulum in vitro and in vivo. - Chemical. CAS: 64-86-8. Formula: C22H25NO6. MW: 399.4. Isolated from Colchicum autumnale. Anti-cancer compound. Microtubule assembly inhibitor. Depolymerizes microtubules and limits microtubule formation (inactivates spindle fibre formation). Inhibits mitosis during cell division at metaphase by inhibiting spindle formation. Anti-inflammatory compound. Suppresses monosodium urate crystal-induced NLRP3/NALP3 inflammasome-driven caspase-1 activation, IL-1beta processing and release, and L-selectin expression on neutrophils at micromolar concentrations. Blocks the release of a crystal-derived chemotactic factor from neutrophil lysosomes, blocks neutrophil adhesion to, and inhibits monosodium urate crystal-induced production of superoxide anions from neutrophils at nanomolar concentrations. Drug used in treatment of gout, familial Mediterranean fever, pericarditis and Behects disease. Investigated for its anti-cancer activity. It has a narrow therapeutic index with no clear-cut distinction between nontoxic, toxic and lethal doses, causing substantial confusion among clinicians. Apoptosis inducer in a variety of normal and tumor cell lines. Inhibitor of autophagosome-lysosome fusion. Inhibits acetylated a-tubulin mediated dynein dependent transport of mitochondria and subsequent apposition of ASC on mitochondria to NLRP3 on the endoplasmic reticulum in vitro and in vivo.
  • SMILES
    COC1=CC2=C(C(OC)=C1OC)C1=CC=C(OC)C(=O)C=C1C(CC2)NC(C)=O
  • Storage Instruction
    -20°C,2°C to 8°C
  • UN Number
    UN 3462
  • UNSPSC
    12352200

References

  • Interactions of colchicine with tubulin: S.B. Hastie; Pharmacol. Ther. 51, 377 (1991) (Review)
  • Analysis of the colchicine-binding site of beta-tubulin: R.G. Burns; FEBS Lett. 297, 205 (1992) (Review)
  • Colchicine induces apoptosis in cerebellar granule cells: E. Bonfoco, et al.; Exp. Cell. Res. 218, 189 (1995)
  • Sustained JNK activation induces endothelial apoptosis: studies with colchicine and shear stress: Y.L. Hu, et al.; Am. J. Physiol. 277, H1593 (1999)
  • Microtubules as a target for anticancer drugs: M.A. Jordan & L. Wilson; Nat. Rev. Cancer 4, 253 (2004)
  • Anti-mitotic activity of colchicine and the structural basis for its interaction with tubulin: B. Bhattacharyya, et al.; Med. Res. Rev. 28, 155 (2008) (Review)
  • Colchicine: its mechanism of action and efficacy in crystal-induced inflammation: G. Nuki; Curr. Rheumatol. Rep. 10, 218 (2008) (Review)
  • Colchicine poisoning: the dark side of an ancient drug: Y. Finkelstein, et al.; Clin. Toxicol. (Phila). 48, 407 (2010) (Review)
  • Colchicine for the treatment of gout: P. Richette & T. Bardin; Expert Opin. Pharmacother. 11, 2933 (2010) (Review)
  • Microtubule-driven spatial arrangement of mitochondria promotes activation of the NLRP3 inflammasome: T. Misawa, et al.; Nat. Immunol. 14, 454 (2013)