Chemical Component Summary

NameN-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]ethanamide
SynonymsCOLCHICINE
IdentifiersN-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]ethanamide
FormulaC22 H25 N O6
Molecular Weight399.437
TypeNON-POLYMER
Isomeric SMILESCC(=O)N[C@H]1CCc2cc(c(c(c2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
InChIInChI=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
InChIKeyIAKHMKGGTNLKSZ-INIZCTEOSA-N

Chemical Details

Formal Charge0
Atom Count54
Chiral Atom Count1
Bond Count56
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB01394 
NameColchicine
Groups approved
DescriptionColchicine is an alkaloid drug derived from a plant belonging to the Lily family, known as _Colchicum autumnale_, or "autumn crocus."[A183611] Its use was first approved by the FDA in 1961.[L8192] Colchicine is used in the treatment of gout flares and Familial Mediterranean fever,[L8138] and prevention of major cardiovascular events.[L47591] It has also been investigated in other inflammatory and fibrotic conditions.[A183602]
Synonyms
  • Colchicin
  • Colchicine
  • Colchicinum
  • Colchicina
Brand Names
  • Colchicine
  • Probenecid and Colchicine
  • Lodoco
  • PMS-colchicine
  • Mitigare
IndicationColchicine is indicated for the prophylaxis and treatment of gout flares. It is also indicated in Familial Mediterranean fever (FMF) in children and adults of four years of age and older.[L8138] It is also indicated to reduce the risk of myocardial infarction (MI), stroke, coronary revascularization, and cardiovascular death in adult patients with established atherosclerotic disease or with multiple risk factors for cardiovascular disease.[L47591] Some off-label uses of colchicine include the treatment of the manifestations of Behcet's syndrome, pericarditis, and postpericardiotomy syndrome.[A183932,A183935]
Categories
  • Agents Causing Muscle Toxicity
  • Alkaloids
  • Antigout Preparations
  • Antimitotic Agents
  • Cytochrome P-450 CYP2B6 Inhibitors
ATC-CodeM04AC01
CAS number64-86-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Tubulin beta chainMREIVHIQAGQCGNQIGAKFWEVISDEHGIDPTGTYHGDSDLQLDRISVY...unknowninhibitor,binder
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
Cytochrome P450 2B6MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...unknowninhibitor
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknowninhibitor
Cytochrome P450 2E1MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...unknowninducer
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL107
PubChem 6167
ChEMBL CHEMBL107
ChEBI CHEBI:27882
CCDC/CSD HOCMOD, COLCDH, HOCMOD01