Colchicine

Colchicine

Clinical data
Trade names	Colcrys
AHFS/Drugs.com	Monograph
MedlinePlus	a682711
Pregnancy category	AU: D US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	M04AC01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	45%
Protein binding	35-44%
Metabolism	Metabolism, partly by CYP3A4
Biological half-life	26.6-31.2 hours
Excretion	Faeces (65%)
Identifiers
IUPAC name N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
CAS Number	64-86-8 Y
PubChem (CID)	6167
IUPHAR/BPS	2367
DrugBank	DB01394 Y
ChemSpider	5933 Y
UNII	SML2Y3J35T Y
KEGG	D00570 Y
ChEBI	CHEBI:27882 Y
ChEMBL	CHEMBL107 Y
ECHA InfoCard	100.000.544
Chemical and physical data
Formula	C22H25NO6
Molar mass	399.437
3D model (Jmol)	Interactive image
SMILES O=C(N[C@@H]3C\1=C\C(=O)C(\OC)=C/C=C/1c2c(cc(OC)c(OC)c2OC)CC3)C
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 Y Key:IAKHMKGGTNLKSZ-INIZCTEOSA-N Y

Colchicine is a medication most commonly used to treat gout. It is a toxic natural product and secondary metabolite, originally extracted from plants of the genus Colchicum (autumn crocus, Colchicum autumnale, also known as "meadow saffron").

Adverse effects are primarily gastrointestinal upset at high doses. In addition to gout, colchicine is used to treat familial Mediterranean fever, pericarditis and Behçet's disease.

Colchicine is an alternative for those unable to tolerate NSAIDs in gout. At high doses, side effects (primarily gastrointestinal upset) limit its use. At lower doses, which are still effective, it is well tolerated.

Colchicine is also used as an anti-inflammatory agent for long-term treatment of Behçet's disease. It appears to have limited effect in relapsing polychondritis, as it may only be useful for the treatment of chondritis and mild skin symptoms.

Colchicine is also used in addition to other therapy in the treatment of pericarditis.

Colchicine is used widely in the treatment of familial Mediterranean fever, in which it reduces attacks and the long-term risk of amyloidosis.

It has been studied for the prevention of postoperative complications after heart surgery. Occurrence of atrial fibrillation can be reduced by a third. It has also been investigated in the prevention and treatment of postpericardiotomy syndrome.

Long-term (prophylactic) regimens of oral colchicine are absolutely contraindicated in patients with advanced renal failure (including those on dialysis). About 10-20 percent of a colchicine dose is excreted unchanged by the kidneys; it is not removed by hemodialysis. Cumulative toxicity is a high probability in this clinical setting, and a severe neuromyopathy may result. The presentation includes a progressive onset of proximal weakness, elevated creatine kinase, and sensorimotor polyneuropathy. Colchicine toxicity can be potentiated by the concomitant use of cholesterol-lowering drugs (statins, fibrates). This neuromuscular condition can be irreversible (even after drug discontinuation). Accompanying dementia has been noted in advanced cases. It may culminate in hypercapnic respiratory failure and death.