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.
OverviewAI-generated
(S)-(−)-colchicine is a chemical compound with the formula C₂₂H₂₅NO₆. Its IUPAC name is N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide. The substance has a mass of 399.168188 and a weight of 399.4. It features a melting point of 156 and a pKa of 12.36. The defined daily dose is 1.
Physicochemical properties include a solubility of 42, an xlogp of 1, and a topological polar surface area of 83.1. The molecule contains one hydrogen bond donor and six hydrogen bond acceptors, with a charge of 0. It is referenced by 1,697 other encyclopedia articles.
Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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.