Colchicine

Colchicine
Skeletal formula of colchicine
Ball-and-stick model of the colchicine molecule
Clinical data
Pronunciation/ˈkɒltʃɪsiːn/ KOL-chiss-een
Trade namesColcrys, Mitigare, others
AHFS/Drugs.comMonograph
MedlinePlusa682711
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability45%
Protein binding35-44%
MetabolismMetabolism, partly by CYP3A4
Elimination half-life26.6-31.2 hours
ExcretionFeces (65%)
Identifiers
  • N-[(7S)-1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.544 Edit this at Wikidata
Chemical and physical data
FormulaC22H25NO6
Molar mass399.443 g·mol−1
3D model (JSmol)
  • CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
  • 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 checkY
  • Key:IAKHMKGGTNLKSZ-INIZCTEOSA-N checkY
  (verify)

Colchicine is a medication used to prevent and treat gout,[3][4] to treat familial Mediterranean fever[5] and Behçet's disease,[6] and to reduce the risk of myocardial infarction.[7] The American College of Rheumatology recommends colchicine, nonsteroidal anti-inflammatory drugs (NSAIDs) or steroids in the treatment of gout.[8][9] Other uses for colchicine include the management of pericarditis.[10]

Colchicine is taken by mouth.[11] The parenteral (injectable) route of administration for colchicine can be lethal, and in 2008, the FDA removed all injectable colchicine from the US market.[12]

Colchicine has a narrow therapeutic index, so overdosing is a significant risk. Common side effects of colchicine include gastrointestinal upset, particularly at high doses.[13] Severe side effects may include pancytopenia (low blood cell counts) and rhabdomyolysis (damage to skeletal muscle), and the medication can be deadly in overdose.[11] Whether colchicine is safe for use during pregnancy is unclear, but its use during breastfeeding appears to be safe.[11][14] Colchicine works by decreasing inflammation via multiple mechanisms.[15]

Colchicine, in the form of the autumn crocus (Colchicum autumnale), was used as early as 1500 BC to treat joint swelling.[16] It was approved for medical use in the United States in 1961.[2] It is available as a generic medication.[14] In 2022, it was the 197th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[17][18]

Colchicine is used in plant breeding to induce polyploidy, in which the number of chromosomes in plant cells are doubled. This helps produce larger, hardier, faster-growing, and in general, more desirable plants than the normally diploid parents.[19]

  1. ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  2. ^ a b "Colchicine capsule". DailyMed. Retrieved 27 March 2019.
  3. ^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 29 May 2024.
  4. ^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 29 May 2024.
  5. ^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 29 May 2024.
  6. ^ Schachner LA, Hansen RC (2011). Pediatric Dermatology E-Book. Elsevier Health Sciences. p. 177. ISBN 978-0-7234-3665-2.
  7. ^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 29 May 2024.
  8. ^ Khanna D, Fitzgerald JD, Khanna PP, Bae S, Singh MK, Neogi T, et al. (October 2012). "2012 American College of Rheumatology guidelines for management of gout. Part 1: systematic nonpharmacologic and pharmacologic therapeutic approaches to hyperuricemia". Arthritis Care & Research. 64 (10): 1431–1446. doi:10.1002/acr.21772. PMC 3683400. PMID 23024028.
  9. ^ Khanna D, Khanna PP, Fitzgerald JD, Singh MK, Bae S, Neogi T, et al. (October 2012). "2012 American College of Rheumatology guidelines for management of gout. Part 2: therapy and antiinflammatory prophylaxis of acute gouty arthritis". Arthritis Care & Research. 64 (10): 1447–1461. doi:10.1002/acr.21773. PMC 3662546. PMID 23024029.
  10. ^ Hutchison SJ (2009). Pericardial Diseases: Clinical Diagnostic Imaging Atlas with DVD. Elsevier Health Sciences. p. 58. ISBN 978-1-4160-5274-6.
  11. ^ a b c "Colchicine Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 27 March 2019.
  12. ^ "FDA Enforcement Against Injectable Colchicine". The Rheumatologist. May 2008. Retrieved 29 May 2024.
  13. ^ "Colchicine for acute gout: updated information about dosing and drug interactions". National Prescribing Service, Australia. 14 May 2010. Archived from the original on 30 June 2012. Retrieved 14 May 2010.
  14. ^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 1085–1086. ISBN 978-0-85711-338-2. "Colchicine". British national formulary. National Institute for Health and Care Excellence (NICE). Retrieved 26 January 2024. Available online in UK only
  15. ^ Dalbeth N, Lauterio TJ, Wolfe HR (October 2014). "Mechanism of action of colchicine in the treatment of gout". Clinical Therapeutics. 36 (10): 1465–1479. doi:10.1016/j.clinthera.2014.07.017. PMID 25151572.
  16. ^ Wall WJ (2015). The Search for Human Chromosomes: A History of Discovery. Springer. p. 88. ISBN 978-3-319-26336-6.
  17. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  18. ^ "Colchicine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  19. ^ Cite error: The named reference Griffiths was invoked but never defined (see the help page).