Compound: colistin
SMILES: O=C1NCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCCC(CC)C)CCN)[C@H](O)C)CCN)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(N[C@H](C(N[C@H](C(N[C@H]1[C@H](O)C)=O)CCN)=O)CCN)=O)CC(C)C)CC(C)C)CCN
InChIKey: YKQOSKADJPQZHB-QNPLFGSASA-N
Synonyms: colistin, 1066-17-7, Colomycin, N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(3S,6S,9S,12S,15R,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, Colymysin S, Z67X93HJG1, Colisticin, Sogecoli, Polymixin E, N-((1S)-3-amino-1-(((1S,2R)-1-(((1S)-3-amino-1-(((3S,6S,9S,12S,15R,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-heptaazacyclotricosan-21-yl)carbamoyl)propyl)carbamoyl)-2-hydroxypropyl)carbamoyl)propyl)-5-methylheptanamide, N-((2S)-4-amino-1-(((2S,3R)-1-(((2S)-4-amino-1-oxo-1-(((3S,6S,9S,12S,15R,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, N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9S,12S,15R,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-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-5-methylheptanamide, RefChem:578510, DTXSID1040663, CHEBI:37943, 213-907-3, N-(4-amino-1-(1-(4-amino-1-oxo-1-(3,12,23-tris(2-aminoethyl)-20-(1-hydroxyethyl)-6,9-diisobutyl-2,5,8,11,14,19,22-heptaoxo-1,4,7,10,13,18-hexaazacyclotricosan-15-ylamino)butan-2-ylamino)-3-hydroxybutan-2-ylamino)-1-oxobutan-2-yl)-N,5-dimethylheptanamide, Colisticina, Colistina, Colistinum, Kangdisu, Kolimitsin, Totazina, SCHEMBL1979092, GTPL10794, YKQOSKADJPQZHB-QNPLFGSASA-N, EX-A15751, DA-62445, NS00006868, G92208, AB01566924_01, Q418946, SR-01000872582, SR-01000872582-1, BRD-A18924964-065-01-5, 5-methylheptanoic acid-Dab-Thr-Dab-Cyclo(Dab-Dab-DLeu-Leu-Dab-Dab-Thr), 1393714-00-5, N-[(1S)-3-amino-1-[[(1S,2R)-1-[[(1S)-3-amino-1-[[(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-diisobutyl-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]carbamoyl]propyl]carbamoyl]-2-hydroxy-propyl]carbamoyl]propyl]-5-methyl-heptanamide
Theoretical properties:
molecular_formula: C52H98N16O13
molecular_weight: 1155.4 g/mol
exact_mass: 1154.74992724 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 18
hydrogen_bond_acceptor_count: 18
rotatable_bond_count: 28
heavy_atom_count: 81
topological_polar_surface_area: 491 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 200-220 °C
Descriptions:
wikipedia: 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.
Colistin was discovered in 1947 and colistimethate sodium was approved for medical use in the United States in 1970. It is on the World Health Organization's List of Essential Medicines. The World Health Organization classifies colistin as critically important for human medicine. It is available as a generic medication. It is derived from bacteria of the genus Paenibacillus.