Structure via PubChem · Public domain (PubChem)
(S)-(−)-colchicine
Sign in to saveAlso known as N-acetyltrimethylcolchicinic acid methyl ether, (S)-N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide, N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide, Colchicine
Colchicine is a medication used to prevent and treat gout, to treat familial Mediterranean fever and Behçet's disease, and to reduce the risk of myocardial infarction. The American College of Rheumatology recommends colchicine, nonsteroidal anti-inflammatory drugs (NSAIDs) or steroids in the treatment of gout. Other uses for colchicine include the management of pericarditis.
Chemical data
- Formula
- C22H25NO6
- Molecular weight
- 399.4 g/mol
- IUPAC name
- N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
- SMILES
- CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
- InChIKey
- IAKHMKGGTNLKSZ-INIZCTEOSA-N
- XLogP
- 1
- Polar surface area
- 83.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
11,657 papers- Colchicine's Role in Cardiovascular Disease Management.Arteriosclerosis, thrombosis, and vascular biology · 2024
- Colchicine in Cardiovascular Disease: In-Depth Review.Circulation · 2022
- Colchicine's Long and Winding Road.Clinical therapeutics · 2023
- Colchicine--Update on mechanisms of action and therapeutic uses.Seminars in arthritis and rheumatism · 2015
- Colchicine poisoning: the dark side of an ancient drug.Clinical toxicology (Philadelphia, Pa.) · 2010
via PubMed
~19 min read
Encyclopedic overview
25 sectionsContents
- Medical uses
- Gout
- Risk of cardiovascular disorders
- Other conditions
- Contraindications
- Adverse effects
- Toxicity
- Mechanism of toxicity
- Epidemiology
- Drug interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- History
- Sources and uses
- Physical properties
- Structure
- Light sensitivity
- Regulation
- Formulations and dosing
- Biosynthesis
- Purification
- Botanical use and seedless fruit
- References
- External links
Colchicine is a medication used to prevent and treat gout, to treat familial Mediterranean fever and Behçet's disease, and to reduce the risk of myocardial infarction. The American College of Rheumatology recommends colchicine, nonsteroidal anti-inflammatory drugs (NSAIDs) or steroids in the treatment of gout. Other uses for colchicine include the management of pericarditis.
Colchicine is taken by mouth. The injectable route of administration for colchicine can be toxic. In 2008, the US Food and Drug Administration removed all injectable colchicine from the US market.
Excerpted from Wikipedia’s “(S)-(−)-colchicine” article, available under the CC BY-SA 4.0 licence.