Colchicine
Vue d'ensemble
Description
Colchicine is a chemical compound derived from the plant Colchicum autumnale, commonly known as the autumn crocus or wild saffron. This ancient drug has been utilized for over 3,000 years, initially documented in the Ebers Papyrus, an Egyptian medical text from around 1550 B.C., where it was prescribed for pain and swelling. The historical significance of this compound is further highlighted by its mention in the writings of Greek physician Pedanius Dioscorides, who recognized its efficacy in treating gout in the 1st century A.D. [“].
The name "this compound" is believed to stem from its use as a poison in ancient Greek mythology, specifically linked to Medea, the daughter of the king of Colchis, who was said to have used it as a deadly toxin[“].
Despite its long history, this compound was only officially approved by the U.S. Food and Drug Administration (FDA) in 2009 for treating gout and familial Mediterranean fever (FMF) under the Unapproved Drugs Initiative . Today, this compound is being explored for various other medical applications, including cardiovascular diseases and even COVID-19 infections[“].
Mécanisme D'action
Colchicine primarily functions by binding to tubulin, a protein essential for microtubule formation. This binding inhibits the assembly and polymerization of microtubules, which are critical for various cellular processes including mitosis. At higher concentrations, this compound can also cause depolymerization of existing microtubules[“].
This compound's effects extend beyond mere cytotoxicity; it modulates immune responses by inhibiting neutrophil chemotaxis, adhesion, and superoxide production. Additionally, it interferes with the NLRP3 inflammasome complex, which plays a significant role in mediating inflammation through interleukin-1β activation[“]. This multifaceted mechanism allows this compound to exert anti-inflammatory effects while minimizing potential toxicities.
Biological Effects
The biological impact of this compound is profound. By disrupting microtubule dynamics, it effectively reduces inflammation associated with conditions like gout and FMF. Furthermore, recent studies have indicated that this compound may also play a role in managing chronic inflammatory diseases through its inhibitory effects on various immune cells[“].
Efficacy and Safety Profile of this compound
Numerous randomized controlled trials have established this compound's effectiveness across different clinical settings. For instance, low-dose this compound has been shown to decrease adverse cardiovascular outcomes significantly[“].
While concerns about gastrointestinal intolerance exist, evidence suggests that low-dose this compound is generally safe when prescribed appropriately. Long-term studies indicate that its use does not significantly increase risks associated with concurrent medications or lead to severe adverse events when monitored correctly [“].
Applications De Recherche Scientifique
Colchicine in Gout Management
This compound is most well-known for its role in managing gout flares. It acts by reducing inflammation caused by uric acid crystals that precipitate in joints, leading to acute arthritis episodes. Compared to other treatments for gout, this compound offers a unique mechanism that targets inflammation directly rather than merely addressing pain[“].
This compound for Familial Mediterranean Fever (FMF)
In patients with FMF, this compound has demonstrated significant efficacy in preventing attacks and managing symptoms. Its ability to modulate inflammatory responses makes it a cornerstone treatment for this hereditary condition[“] .
This compound in Cardiovascular Disease
Recent clinical trials have highlighted this compound's potential benefits in cardiovascular disease management. Studies such as LoDoCo and COLCOT have shown that low-dose this compound can significantly reduce the risk of myocardial infarction and stroke when used alongside standard therapies like antiplatelet agents and statins[“]. This emerging role positions this compound as an attractive option for secondary prevention strategies in patients with cardiovascular conditions.
Potential Uses in Other Conditions
Beyond gout and FMF, this compound is being investigated for its therapeutic potential in various conditions:
Atrial Fibrillation: Research indicates that this compound may help reduce recurrence rates.
COVID-19: Preliminary studies suggest it might mitigate inflammatory responses associated with severe cases[“].
Common Problem
What is colchicine used for?
This compound is primarily used to treat gout flares and familial Mediterranean fever but is also being studied for cardiovascular diseases and other inflammatory conditions.
How does this compound work?
It works by binding to tubulin, disrupting microtubule formation which leads to reduced inflammation through various immune modulation pathways.
Is this compound safe for long-term use?
When used at low doses under medical supervision, this compound has been found safe for long-term use without significant adverse effects.
Can this compound be used in combination with other medications?
Yes, low-dose this compound can be safely used alongside other medications commonly prescribed for cardiovascular diseases without increasing risks significantly.
Propriétés
IUPAC Name |
N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide |
Source
|
|---|---|---|
| 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
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
IAKHMKGGTNLKSZ-INIZCTEOSA-N |
Source
|
| 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
|
| 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
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C22H25NO6 |
Source
|
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID5024845 |
Source
|
| 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
|
| 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) |
Source
|
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
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 |
Source
|
| 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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| Record name | COLCHICINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. | |
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. |
Source
|
| Record name | COLCHICINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. |
Source
|
| Record name | COLCHICINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. | |
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 |
Source
|
| 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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| Record name | Colchicine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=64-86-8 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Colchicine [USP:JAN] | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000064868 | |
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| Record name | colchicine | |
| Source | DTP/NCI | |
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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]- | |
| Source | EPA Chemicals under the TSCA | |
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| Record name | Colchicine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID5024845 | |
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| Record name | Colchicine | |
| Source | European Chemicals Agency (ECHA) | |
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| Record name | Colchicine | |
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| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/SML2Y3J35T | |
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| Record name | COLCHICINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. | |
Melting Point |
288 to 302 °F (EPA, 1998), 142-150 °C |
Source
|
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | COLCHICINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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. | |
Synthesis routes and methods
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Veuillez noter que tous les articles et informations sur les produits présentés sur BenchChem sont destinés uniquement à des fins informatives. Les produits disponibles à l'achat sur BenchChem sont spécifiquement conçus pour des études in vitro, qui sont réalisées en dehors des organismes vivants. Les études in vitro, dérivées du terme latin "in verre", impliquent des expériences réalisées dans des environnements de laboratoire contrôlés à l'aide de cellules ou de tissus. Il est important de noter que ces produits ne sont pas classés comme médicaments et n'ont pas reçu l'approbation de la FDA pour la prévention, le traitement ou la guérison de toute condition médicale, affection ou maladie. Nous devons souligner que toute forme d'introduction corporelle de ces produits chez les humains ou les animaux est strictement interdite par la loi. Il est essentiel de respecter ces directives pour assurer la conformité aux normes légales et éthiques en matière de recherche et d'expérimentation.
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