Colistin

Synonym(s): Polymyxin E

Class: Polymyxin

Spectrum of activity:	Gram-negative
Details of activity:	Disrupts the outer membrane by direct interaction with the lipid A component of the LPS and and disrupts the physical integrity of the phospholipid bilayer of the inner membrane, and possibly additional modes of action. Active against Gram-negative bacteria including Acinetobacter and Pseudomonas
Description:	Natural product produced by Bacillus colistinus composed of a mixture of Polymyxins E1 and E2 (or Colistins A, B, and C). For systemic treatment it is used as the prodrug Colistimethate sodium (CMS) for topical use as Colistin sulfate. Nephrotoxic but still active in most cases of pan drug resistant Gram-negative bacteria.
Year first mentioned:	1947
Development status:	Approved, off-patent

Chemical structure(s):
Canonical 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@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O
Isomeric 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@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CCN)CC(C)C)CC(C)C)CCN)CCN)[C@@H](C)O
InChI:	InChI=1S/C52H98N16O13/c1-9-29(6)11-10-12-40(71)59-32(13-19-53)47(76)68-42(31(8)70)52(81)64-35(16-22-56)44(73)63-37-18-24-58-51(80)41(30(7)69)67-48(77)36(17-23-57)61-43(72)33(14-20-54)62-49(78)38(25-27(2)3)66-50(79)39(26-28(4)5)65-45(74)34(15-21-55)60-46(37)75/h27-39,41-42,69-70H,9-26,53-57H2,1-8H3,(H,58,80)(H,59,71)(H,60,75)(H,61,72)(H,62,78)(H,63,73)(H,64,81)(H,65,74)(H,66,79)(H,67,77)(H,68,76)/t29?,30-,31-,32+,33+,34+,35+,36+,37+,38+,39-,41+,42+/m1/s1
InChI Key:	YKQOSKADJPQZHB-QNPLFGSASA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/5311054

External links:
Guide to Pharmacology:	colistin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/25459221/
Citations:	https://pubmed.ncbi.nlm.nih.gov/29456043/ https://www.clinicalmicrobiologyandinfection.com/article/S1198-743X(14)62699-9/fulltext