Colchicine
Overview
Description
Colchicine is a naturally occurring alkaloid derived from the plants Colchicum autumnale (autumn crocus) and Gloriosa superba (glory lily) . It has been used for centuries in traditional medicine and is primarily known for its effectiveness in treating gout and familial Mediterranean fever . This compound is also utilized in the treatment of various other inflammatory conditions, including Behçet’s disease, pericarditis, and amyloidosis .
Mechanism of Action
Target of Action
Colchicine primarily targets microtubules , a component of the cell’s cytoskeleton . Microtubules play a crucial role in maintaining cell shape, signaling, division, migration, and cellular transport .
Mode of Action
This compound exerts its unique action mainly through the inhibition of microtubule polymerization . This interaction with microtubules leads to the disruption of various cellular processes, including the migration of white blood cells called neutrophils . By binding to neutrophils, this compound prevents these cells from migrating to areas where uric acid crystals have accumulated, thereby tempering the inflammatory response .
Biochemical Pathways
This compound affects several biochemical pathways. It interferes with the assembly of the NLRP3 inflammasome complex present in neutrophils and monocytes, which mediates the activation of interleukin-1β , an inflammatory mediator . Additionally, this compound attenuates neutrophil activation and the release of other inflammatory mediators .
Pharmacokinetics
This compound is a tricyclic, lipid-soluble alkaloid predominantly metabolized in the gastrointestinal tract . Two proteins, P-glycoprotein (P-gp) and CYP3A4 , play a pivotal role in governing its pharmacokinetics . This compound is excreted mainly by the biliary system, intestines, and the kidneys .
Result of Action
The molecular and cellular effects of this compound’s action are primarily anti-inflammatory. It inhibits neutrophil activation and the release of inflammatory mediators, leading to a reduction in inflammation . At the cellular level, this compound inhibits endothelial cell dysfunction and inflammation, smooth muscle cell proliferation and migration, macrophage chemotaxis, migration, and adhesion, and platelet activation .
Action Environment
The action, efficacy, and stability of this compound can be influenced by various environmental factors. For instance, the presence of other drugs can affect the blood level of this compound, as many drugs can inhibit cytochrome 3A4, which metabolizes this compound . Therefore, caution should be exercised when such medications are added. Furthermore, the effectiveness of this compound can be affected by the patient’s liver and kidney functions .
Safety and Hazards
Colchicine may cause serious side effects, including muscle pain or weakness, numbness or tingly feeling in your fingers or toes, pale or gray appearance of your lips, tongue, or hands, severe or ongoing vomiting or diarrhea, fever, chills, body aches, flu symptoms, or easy bruising, unusual bleeding, feeling weak or tired . It is also highly toxic and can be deadly in overdose .
Future Directions
The long-term use of colchicine is established for FMF and the prophylaxis of gout flares, but the safety and efficacy of repeat treatment for gout flares have not been evaluated . Most people take small amounts of it regularly for a long time (months or even years) to prevent severe attacks or other problems caused by inflammation .
Biochemical Analysis
Biochemical Properties
Colchicine interacts with protein filaments called microtubules, inhibiting their formation and thereby arresting cell division . This interaction is due to the unique molecular structure of this compound, which contains an unusual system of rings and a stereocentre .
Cellular Effects
This compound has a profound effect on various types of cells and cellular processes. It influences cell function by impacting cell signaling pathways, gene expression, and cellular metabolism . For instance, it has been observed to reduce a membrane-associated DNA-binding protein during the meiotic prophase .
Molecular Mechanism
This compound exerts its effects at the molecular level through binding interactions with biomolecules, enzyme inhibition or activation, and changes in gene expression . Its binding to microtubules prevents their polymerization, disrupting the formation of the mitotic spindle necessary for cell division .
Temporal Effects in Laboratory Settings
The effects of this compound change over time in laboratory settings. Information on its stability, degradation, and long-term effects on cellular function is observed in in vitro or in vivo studies .
Dosage Effects in Animal Models
The effects of this compound vary with different dosages in animal models. High doses can lead to toxic or adverse effects .
Metabolic Pathways
This compound is involved in several metabolic pathways. It interacts with enzymes and cofactors, and can affect metabolic flux or metabolite levels .
Transport and Distribution
This compound is transported and distributed within cells and tissues. It interacts with transporters or binding proteins, affecting its localization or accumulation .
Subcellular Localization
This compound’s subcellular localization and its effects on activity or function are significant. It may be directed to specific compartments or organelles by targeting signals or post-translational modifications .
Preparation Methods
Synthetic Routes and Reaction Conditions: The preparation of colchicine involves several steps, including extraction from plant sources and chemical synthesis. One common method involves ultrasonic-assisted dual-water phase extraction . The process includes grinding the raw material containing this compound, performing dual-water phase extraction under ultrasonic waves, concentrating the extract, adding chloroform, and filtering. The filtrate is then separated using a macroporous absorption resin column, eluted, concentrated, crystallized, and dried to obtain pure this compound .
Industrial Production Methods: Industrial production of this compound follows similar extraction and purification processes but on a larger scale. The use of advanced techniques like ultrasonic-assisted extraction ensures higher yields and efficiency .
Chemical Reactions Analysis
Types of Reactions: Colchicine undergoes various chemical reactions, including oxidation, reduction, and substitution.
Common Reagents and Conditions:
Oxidation: this compound can be oxidized using reagents like potassium permanganate or hydrogen peroxide under controlled conditions.
Reduction: Reduction of this compound can be achieved using reducing agents such as sodium borohydride.
Substitution: Substitution reactions often involve nucleophiles like amines or thiols.
Major Products Formed: The major products formed from these reactions depend on the specific reagents and conditions used. For example, oxidation may yield this compound derivatives with altered functional groups, while reduction can lead to the formation of dihydrothis compound .
Scientific Research Applications
Colchicine has a wide range of scientific research applications:
Chemistry: Used as a reagent in various chemical reactions and studies involving microtubule polymerization.
Medicine: Apart from treating gout and familial Mediterranean fever, this compound is being investigated for its potential in treating cardiovascular diseases, including coronary artery disease and atherosclerosis.
Comparison with Similar Compounds
Vincristine: Another alkaloid that inhibits microtubule formation, used in cancer therapy.
Vinblastine: Similar to vincristine, used in the treatment of various cancers.
Podophyllin: An antitubulin agent with similar mechanisms of action.
Uniqueness of Colchicine: this compound’s unique ability to inhibit microtubule polymerization without causing significant cytotoxicity makes it distinct from other similar compounds . Its effectiveness in treating a wide range of inflammatory conditions and its potential in cardiovascular therapy further highlight its uniqueness .
Properties
IUPAC Name |
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide | |
---|---|---|
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1 | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
InChI Key |
IAKHMKGGTNLKSZ-INIZCTEOSA-N | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C22H25NO6 | |
Record name | COLCHICINE | |
Source | CAMEO Chemicals | |
URL | https://cameochemicals.noaa.gov/chemical/4925 | |
Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID5024845 | |
Record name | Colchicine | |
Source | EPA DSSTox | |
URL | https://comptox.epa.gov/dashboard/DTXSID5024845 | |
Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
399.4 g/mol | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Physical Description |
Colchicine appears as odorless or nearly odorless pale yellow needles or powder that darkens on exposure to light. Used to treat gouty arthritis, pseudogout, sarcoidal arthritis and calcific tendinitis. (EPA, 1998) | |
Record name | COLCHICINE | |
Source | CAMEO Chemicals | |
URL | https://cameochemicals.noaa.gov/chemical/4925 | |
Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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Solubility |
greater than or equal to 100 mg/mL at 70 °F (NTP, 1992), 1 g dissolves in 22 mL water, 220 mL ether, 100 mL benzene; freely sol in alcohol or chloroform; practically insoluble in petroleum ether, SOL IN METHANOL; SLIGHTLY SOL IN CARBON TETRACHLORIDE, At 25 °C, 4.5 g/100 g water | |
Record name | COLCHICINE | |
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Record name | COLCHICINE | |
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URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3044 | |
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Mechanism of Action |
... HUVEC cells were exposed to various concentrations of colchicine and were harvested at different time points. Ribonucleic acid was extracted, amplified, reverse transcribed and hybridized to complementary deoxyribonucleic acid microarrrays containing more than 40,000 probes to human expressed sequence tags. This approach enabled us to have a global look at the transcriptional response induced by colchicine treatment. Colchicine changed the expression of many genes in HUVEC cells following exposure to a concentration of 100 ng/ml or higher. Following short exposure (30 or 120 min), colchicine affected genes known to be involved in the cell cycle and its regulation. However, change in expression of genes involved in neutrophil migration or other inflammatory processes were observed mainly after 12 to 24 hr. The anti-inflammatory effect of colchicine may be mediated not only through direct interaction with microtubules but also through changes at the transcriptional level. This latter effect apparently requires a higher concentration and a longer time to occur., Colchicine, long used to treat gout, arrests microtubule assembly and inhibits many cellular functions. At micromolar concentrations, it suppresses monosodium urate crystal-induced NACHT-LRR-PYD-containing protein-3 (NALP3) inflammasome-driven caspase-1 activation, IL-1beta processing and release, and L-selectin expression on neutrophils. At nanomolar concentrations, colchicine blocks the release of a crystal-derived chemotactic factor from neutrophil lysosomes, blocks neutrophil adhesion to endothelium by modulating the distribution of adhesion molecules on the endothelial cells, and inhibits monosodium urate crystal-induced production of superoxide anions from neutrophils. Cyto-chrome P450 3A4, the multidrug transporter P-glycoprotein, and the drugs that bind these proteins influence its pharmacokinetics and pharmacodynamics. Trial evidence supports its efficacy in acute gout and in preventing gout flares, but it has narrow therapeutic index, and overdosage is associated with gastrointestinal, hepatic, renal, neuromuscular, and cerebral toxicity; bone marrow damage; and high mortality., The actions of colchicine were examined with the two-electrode voltage-clamp technique and radioligand binding assays in mouse and human 5-hydroxytryptamine(3A) receptors (5-HT(3A)Rs) expressed in Xenopus laevis oocytes. Colchicine inhibited 5-hydroxytryptamine (5-HT)-evoked currents in oocytes expressing mouse 5-HT(3A)Rs, with an IC(50) of 59.5 +/- 3 uM. In contrast to the mouse receptor, coapplication of colchicine with 5-HT (<1 uM) strongly enhanced 5-HT-evoked currents in oocytes expressing human 5-HT(3A)Rs. Colchicine applied alone did not induce a detectable current. In the presence of 0.5 microM 5-HT, the potentiation was concentration-dependent and reached the maximum (approximately 100%) when 750 microM colchicine was applied. However, colchicine-dependent inhibition can be observed at 5-HT concentrations > 1 uM. In oocyte membranes expressing mouse or human receptors, binding studies with colchicine (25 nM-1 mM) revealed no displacement of 1-methyl-N-((1R,3r,5S)-9-methyl-9 azabicyclo [3.3.1]nonan-3yl)-1H-indazole-3 carboxamide ([(3)H]BRL-43694), suggesting that actions of colchicine do not occur at the ligand binding domain. Functional effects of colchicine on both receptors occurred in the absence of preincubation and after cold temperature incubation, suggesting that the microtubule-depolymerizing effects of colchicine play no role in modulation of receptor function. Studies with interspecies chimeric receptors demonstrated that the distal one third of the N terminus is responsible for the bidirectional modulation by colchicine. Collectively, these results suggest that colchicine modulates receptor function through loops C and/or F through a gating mechanism., Colchicine exerts a variety of pharmacological effects, but how these occur or how they relate to its activity in gout is not well understood. It has antimitotic effects, arresting cell division in GI by interfering with microtubule and spindle formation (an effect shared with vinca alkaloids). This effect is greatest on cells with rapid turnover (e.g., neutrophils and GI epithelium). Although somewhat controversial, colchicine may alter neutrophil motility in ex vivo assays. Colchicine also renders cell membranes more rigid and decreases the secretion of chemotactic factors by activated neutrophils., For more Mechanism of Action (Complete) data for COLCHICINE (8 total), please visit the HSDB record page. | |
Record name | COLCHICINE | |
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URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3044 | |
Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Impurities |
Beta-lumicolchicine, Colchiceine, Colchicoside, N-deacetyl-N-formylcolchicine, For more Impurities (Complete) data for COLCHICINE (6 total), please visit the HSDB record page. | |
Record name | COLCHICINE | |
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Color/Form |
Pale yellow scales or powder; pale yellow needles when crystallized from ethyl acetate, Yellow plates from water + 1/2 mol of water of crystallization; yellow crystals from benzene | |
CAS No. |
64-86-8 | |
Record name | COLCHICINE | |
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Record name | Colchicine | |
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Record name | Acetamide, N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]- | |
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Record name | Colchicine | |
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Record name | COLCHICINE | |
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Melting Point |
288 to 302 °F (EPA, 1998), 142-150 °C | |
Record name | COLCHICINE | |
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URL | https://cameochemicals.noaa.gov/chemical/4925 | |
Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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Record name | COLCHICINE | |
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