Structure via PubChem · Public domain (PubChem)
colistin
Sign in to saveAlso known as Polymyxin E, Colistina, Colistine, Colistinum
Colistin, also known as polymyxin E, is an antibiotic medication used as a last-resort treatment for multidrug-resistant Gram-negative infections including pneumonia. These may involve bacteria such as Pseudomonas aeruginosa, carbapenem-resistant Klebsiella pneumoniae (CRKP), or Acinetobacter. It comes in two forms: colistimethate sodium can be injected into a vein, injected into a muscle, or inhaled, and colistin sulfate is mainly applied to the skin or taken by mouth. Colistimethate sodium is a prodrug; it is produced by the reaction of colistin with formaldehyde and sodium bisulfite, which
Chemical data
- Formula
- C52H98N16O13
- Molecular weight
- 1155.4 g/mol
- IUPAC name
- N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(6R,9S,12R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-5-methylheptanamide
- SMILES
- CCC(C)CCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)C(NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(NC(=O)[C@@H](NC1=O)CCN)CC(C)C)CC(C)C)CCN)CCN)[C@@H](C)O
- InChIKey
- YKQOSKADJPQZHB-BRLOSWAASA-N
- XLogP
- -3.3
- Polar surface area
- 491 Ų
- H-bond donors
- 18
- H-bond acceptors
- 18
- Formal charge
- 0
via PubChem
Research
13,651 papers- Colistin resistance mechanisms in Gram-negative bacteria: a Focus on Escherichia coli.Letters in applied microbiology · 2023
- Colistin Resistance in Enterobacterales Strains - A Current View.Polish journal of microbiology · 2019
- Farm to table: colistin resistance hitchhiking through food.Archives of microbiology · 2023
- Colistin Resistance in Acinetobacter baumannii: Basic and Clinical Insights.Biological & pharmaceutical bulletin · 2025
- Global colistin use: a review of the emergence of resistant Enterobacterales and the impact on their genetic basis.FEMS microbiology reviews · 2022
via PubMed
Wikidata facts
- Image
- Colistin Function.jpg
Show 3 more facts
- canonical SMILES
- CCC(C)CCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)CC(C)C)CC(C)C)CCN)CCN)C(C)O
- Commons category
- Colistin
- NCI Thesaurus ID
- C65350
Sources (2)
via Wikidata · CC0
~15 min read
Article
16 sectionsContents
- Medical uses
- Antibacterial spectrum
- Administration and dosage
- Forms
- Dosage
- Resistance
- Inherently resistant
- Variable resistance
- Adverse reactions
- Mechanism of action
- Pharmacokinetics
- History
- Biosynthesis
- References
- Further reading
- External links
Colistin, also known as polymyxin E, is an antibiotic medication used as a last-resort treatment for multidrug-resistant Gram-negative infections including pneumonia. These may involve bacteria such as Pseudomonas aeruginosa, carbapenem-resistant Klebsiella pneumoniae (CRKP), or Acinetobacter. It comes in two forms: colistimethate sodium can be injected into a vein, injected into a muscle, or inhaled, and colistin sulfate is mainly applied to the skin or taken by mouth. Colistimethate sodium is a prodrug; it is produced by the reaction of colistin with formaldehyde and sodium bisulfite, which leads to the addition of a sulfomethyl group to the primary amines of colistin. Colistimethate sodium is less toxic than colistin when administered parenterally. In aqueous solutions, it undergoes hydrolysis to form a complex mixture of partially sulfomethylated derivatives, as well as colistin. Resistance to colistin began to appear as of 2015.
Common side effects of the injectable form include kidney problems and neurological problems. Other serious side effects may include anaphylaxis, muscle weakness, and Clostridioides difficile-associated diarrhea. The inhaled form may result in constriction of the bronchioles. It is unclear if use during pregnancy is safe for the fetus. Colistin is in the polymyxin class of medications. It works by breaking down the cytoplasmic membrane, which generally results in bacterial cell death.