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colistin

Structure via PubChem · Public domain (PubChem)

EntityQ418946· pop 28· linked from 168 articles

Also 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

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 sections
Contents
  • 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.

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