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Summary
General Info

PubChem

PubChem Compound 2833

PubChem Compound 2833

Name:	Colchicine
PubChem Compound ID:	2833
Description:	A major alkaloid from Colchicum autumnale L. and found also in other Colchicum species. Its primary therapeutic use is in the treatment of gout, but it has been used also in the therapy of familial Mediterranean fever (PERIODIC DISEASE).
Molecular formula:	C₂₂H₂₅NO₆
Molecular weight:	399.437 g/mol
Synonyms:	Colchicine, (+)-; Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-; Colchine; Colchicine

DrugBank

Identification

Name:	Colchicine
Name (isomeric):	DB01394
Drug Type:	small molecule
Description:	A major alkaloid from Colchicum autumnale L. and found also in other Colchicum species. Its primary therapeutic use is in the treatment of gout, but it has been used also in the therapy of familial Mediterranean fever (PERIODIC DISEASE).
Synonyms:	Colchicinum; Colchicin; Colchicina
Brand:	Condylon, Proben-C, Col-probenecid, Colbenemid
Brand name mixture:	Sciat HP(Aconitinum + Arnica Montana + Colchicine + Esculin + Hypericum Perforatum + Magnesium Phosphate Dibasic + Plumbum Metallicum + Poison Ivy), Sucurnix HP(Colchicine + Eugenia Jambolana + Lactic Acid + Lycopodium Clavatum + Phosphoric Acid + Phosphorus + Uranium Nitrate), Art HP(Apis Mellifica + Bryonia + Colchicine + Hahnemann's Causticum... show more » Sciat HP(Aconitinum + Arnica Montana + Colchicine + Esculin + Hypericum Perforatum + Magnesium Phosphate Dibasic + Plumbum Metallicum + Poison Ivy), Sucurnix HP(Colchicine + Eugenia Jambolana + Lactic Acid + Lycopodium Clavatum + Phosphoric Acid + Phosphorus + Uranium Nitrate), Art HP(Apis Mellifica + Bryonia + Colchicine + Hahnemann's Causticum + Ivy + Ledum Palustre + Poison Ivy + Pulsatilla + Rhododendron Chrysanthemum), Arnix Gel(Colchicine + Hahnemann's Causticum + Ivy + Ledum Palustre + Poison Ivy + Propolis + Rhododendron Chrysanthemum + Thuja Occidentalis), Edma HP(Apis Mellifica + Cinchona Officinalis + Colchicine + Ledum Palustre + Lycopodium Clavatum + Poison Ivy + Sambucus Nigra + Strophanthus Hispidus), Edemnix HP(Apis Mellifica + Cinchona Officinalis + Colchicine + Ledum Palustre + Lycopodium Clavatum + Poison Ivy + Sambucus Nigra + Strophanthus Hispidus), Arnix HP(Apis Mellifica + Bryonia + Colchicine + Hahnemann's Causticum + Ivy + Ledum Palustre + Poison Ivy + Pulsatilla + Rhododendron Chrysanthemum), Sciatinix HP(Aconitinum + Arnica Montana + Colchicine + Esculin + Hypericum Perforatum + Magnesium Phosphate Dibasic + Plumbum Metallicum + Poison Ivy), Jnt-Nix HP(Bryonia + Colchicine + Kalmia Latifolia + Ledum Palustre + Lycopodium Clavatum + Poison Ivy + Rhododendron Chrysanthemum), DB HP(Colchicine + Eugenia Jambolana + Lactic Acid + Lycopodium Clavatum + Phosphoric Acid + Phosphorus + Uranium Nitrate) show less «
Category:	Tubulin Modulators, Gout Suppressants
CAS number:	64-86-8

Pharmacology

Indication:	For treatment and relief of pain in attacks of acute gouty arthritis.
Pharmacology:	Colchicine is a highly poisonous alkaloid, originally extracted from plants of the genus Colchicum (Autumn crocus, also known as the "Meadow saffron"). Originally used to treat rheumatic complaints and especially gout, it was also prescribed for its cathartic and emetic effects. Its present medicinal use is mainly in the treatment of gout; as well,... show more » Colchicine is a highly poisonous alkaloid, originally extracted from plants of the genus Colchicum (Autumn crocus, also known as the "Meadow saffron"). Originally used to treat rheumatic complaints and especially gout, it was also prescribed for its cathartic and emetic effects. Its present medicinal use is mainly in the treatment of gout; as well, it is being investigated for its potential use as an anti-cancer drug. It can also be used as initial treatment for pericarditis and preventing recurrences of the condition. show less «
Mechanism of Action:	The precise mechanism of action has not been completely established. In patients with gout, colchicine apparently interrupts the cycle of monosodium urate crystal deposition in joint tissues and the resultant inflammatory response that initiates and sustains an acute attack. Colchicine decreases leukocyte chemotaxis and phagocytosis and inhibits th... show more » The precise mechanism of action has not been completely established. In patients with gout, colchicine apparently interrupts the cycle of monosodium urate crystal deposition in joint tissues and the resultant inflammatory response that initiates and sustains an acute attack. Colchicine decreases leukocyte chemotaxis and phagocytosis and inhibits the formation and release of a chemotactic glycoprotein that is produced during phagocytosis of urate crystals. Colchicine also inhibits urate crystal deposition, which is enhanced by a low pH in the tissues, probably by inhibiting oxidation of glucose and subsequent lactic acid production in leukocytes. Colchicine has no analgesic or antihyperuricemic activity. Colchicine inhibits microtubule assembly in various cells, including leukocytes, probably by binding to and interfering with polymerization of the microtubule subunit tubulin. Although some studies have found that this action probably does not contribute significantly to colchicine's antigout action, a recent in vitro study has shown that it may be at least partially involved. show less «
Absorption:	Colchicine is rapidly absorbed after oral administration, probably from the jejunum and ileum. However, the rate and extent of absorption are variable, depending on the tablet dissolution rate; variability in gastric emptying, intestinal motility, and pH at the absorption site; and the extent to which colchicine is bound to microtubules in gastrointestinal mucosal cells.
Protein binding:	Low to moderate (30 to 50%).
Biotransformation:	Probably hepatic. Although colchicine metabolites have not been identified in humans, metabolism by mammalian hepatic microsomes has been demonstrated in vitro.
Route of elimination:	In healthy volunteers (n=12) 40 – 65% of 1 mg orally administered colchicine was recovered unchanged in urine. Enterohepatic recirculation and biliary excretion are also postulated to play a role in colchicine elimination.
Half Life:	Elimination half-life is approximately 1 hour in healthy subjects, although a study with an extended sampling time reported mean terminal elimination half-life values of approximately 9 to 10.5 hours. Other studies have reported half-life values of approximately 2 hours in patients with alcoholic cirrhosis and approximately 2.5 hours in patients with familial Mediterranean fever.
Clearance:	0.17 L/hr/kg [familial Mediterranean fever patients with end-stage renal disease] 0.73 L/hr/kg [familial Mediterranean fever patients with normal renal function]
Toxicity:	The onset of toxic effects is usually delayed for several hours or more after the ingestion of an acute overdose. Nausea, vomiting, abdominal pain, and diarrhea occur first. The diarrhea may be bloody due to hemorrhagic gastroenteritis. Burning sensations of the throat, stomach, and skin may be prominent symptoms. Extensive vascular damage may result in shock. Kidney damage, evidenced by hematuria and oliguria, may occur. Muscular weakness may be marked, and ascending paralysis of the central nervous system may develop; the patient usually remains conscious. Delirium and convulsions may occur. Death due to respiratory arrest may result. Although death from the ingestion of as little as 7 mg has been reported, much larger doses have been survived .
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Drink liberally.

Avoid alcohol since it increases uric acid levels.

Take without regard to meals.

Drug interaction:

Conivaptan	CYP3A4 Inhibitors (Strong) may increase the serum concentration of Colchicine. In patients with normal renal and hepatic function, reduce colchicine dose (for gout flares: to 0.6 mg x 1 dose, followed by 0.3 mg 1 hour later, with next dose no sooner than 3 days later; for gout flare prophylaxis: if target dose would otherwise be 0.6 mg daily, change to 0.3 mg every other day, and if target dose would otherwise be 0.6 mg twice daily, change to 0.3 mg daily; for Familial Mediterranean Fever: to no more than 0.6 mg/day) when using in combination with a strong CYP3A4 inhibitor such as clarithromycin or ritonavir. Increase monitoring for colchicine-related toxicity when using such combinations. Colchicine use is contraindicated in patients with impaired renal and/or hepatic function who are also receiving a strong CYP3A4 inhibitor.
Fluvastatin	Increased risk of rhabdomyolysis with this combination
Simvastatin	Increased risk of rhabdomyolysis with this combination
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of colchicine by decreasing its metabolism. A dose reduction of colchicine is recommended along with increased monitoring for colchicine toxicity. Concomitant therapy is contraindicated in patients with renal and/or hepatic impairment.
Troleandomycin	Severe colchicine toxicity can occur

Conivaptan	CYP3A4 Inhibitors (Strong) may increase the serum concentration of Colchicine. In patients with normal renal and hepatic function, reduce colchicine dose (for gout flares: to 0.6 mg x 1 dose, followed by 0.3 mg 1 hour later, with next dose no sooner than 3 days later; for gout flare prophylaxis: if target dose would otherwise be 0.6 mg daily, change to 0.3 mg every other day, and if target dose would otherwise be 0.6 mg twice daily, change to 0.3 mg daily; for Familial Mediterranean Fever: to no more than 0.6 mg/day) when using in combination with a strong CYP3A4 inhibitor such as clarithromycin or ritonavir. Increase monitoring for colchicine-related toxicity when using such combinations. Colchicine use is contraindicated in patients with impaired renal and/or hepatic function who are also receiving a strong CYP3A4 inhibitor.
Fluvastatin	Increased risk of rhabdomyolysis with this combination
Simvastatin	Increased risk of rhabdomyolysis with this combination
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of colchicine by decreasing its metabolism. A dose reduction of colchicine is recommended along with increased monitoring for colchicine toxicity. Concomitant therapy is contraindicated in patients with renal and/or hepatic impairment.
Troleandomycin	Severe colchicine toxicity can occur
Atorvastatin	Increased risk of rhadbomyolysis with this combination.
Cerivastatin	Increased risk of rhabdomyolysis with this combination
Cyclosporine	Increased toxicity of both drugs
Clarithromycin	Severe colchicine toxicity can occur
Telithromycin	Telithromycin may reduce clearance of Colchicine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Colchicine if Telithromycin is initiated, discontinued or dose changed.
Pravastatin	Increased risk of rhabdomyolysis with this combination
Erythromycin	Severe colchicine toxicity can occur
Verapamil	Verapamil may increase the serum concentration of Colchicine. This likely occurs via Verapamil-mediated inhibition of CYP3A4 and p-glycoprotein-mediated transport. Monitor for changes in the therapeutic/adverse effects of Colchicine if Verapamil is initiated, discontinued or dose changed.
Lovastatin	Increased risk of rhabdomyolysis with this combination
Clotrimazole	CYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of colchicine. Reduce colchicine dose (for gout flares: to 1.2 mg x 1 dose, with next dose no sooner than 3 days later; for Familial Mediterranean Fever: to no more than 1.2 mg/day) when using in combination with a moderate CYP3A4 inhibitor such as erythromycin or verapamil. Increase monitoring for colchicine-related toxicity when using such combinations. Use extra caution in patients with impaired renal and/or hepatic function.
Rosuvastatin	Increased risk of rhabdomyolysis with this combination
Bicalutamide	CYP3A4 Inhibitors like bicalutamide may increase the serum concentration of colchicine. Increase monitoring for colchicine-related toxicity when using such combinations. Use extra caution in patients with impaired renal and/or hepatic function.

Targets

Tubulin beta-1 chain

Tubulin beta chain

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2B6

Cytochrome P450 2C8

Cytochrome P450 2C9

Cytochrome P450 2E1

Transporters

Multidrug resistance protein 3

Solute carrier family 22 member 3

Multidrug resistance protein 1

Multidrug resistance-associated protein 1