Colistin

Title: Colistin
CAS Registry Number: 1066-17-7
Additional Names: Polymyxin E
Literature References: Cyclic polypeptide antibiotic produced by Bacillus polymyxa subsp. colistinus. Complex mixture of at least 30 components, primarily colistins A and B. Isoln from Japanese soil: Y. Koyama, JP 52 1546 (1952). Identification of colistins A, B and C: T. Suzuki et al., J. Biochem. (Tokyo) 54, 25 (1963). Structure of colistin A: eidem, ibid. 173, 412. Identity of colistin A with polymyxin E1: S. Wilkinson, L. A. Lowe, J. Chem. Soc. 1964, 4107. Synthesis of colistin A: R. O. Studer et al., Helv. Chim. Acta 48, 1371 (1965). Prepn of sodium sulfomethyl derivs and toxicity study: M. Barnett et al., Br. J. Pharmacol. Chemother. 23, 552 (1964). Comparative pharmacology of sulfate and methansulfonate salts: A. A. Al-Khayyat, A. L. Aronson, Chemotherapy (Basel) 19, 82 (1973). HPLC determn in medicated animal feeds: B. Cancho-Grande et al., Chromatagraphia 54, 481 (2001); in human plasma: J. Li et al., J. Chromatogr. B 761, 167 (2001). Review and comparison with polymyxin B, q.v.: J. Horton, G. A. Pankey, Med. Clin. North Am. 66, 135-142 (1982); M. E. Evans et al, Ann. Pharmacother. 33, 960-967 (1999). Review of clinical experience in cystic fibrosis: J. M. Littlewood et al., Respir. Med. 94, 632 (2000); in treatment of multi-resistant bacterial infections: J. Li et al., Int. J. Antimicrob. Ag. 25, 11-25 (2005).
Derivative Type: Colistin sodium methanesulfonate
CAS Registry Number: 8068-28-8
Additional Names: Colistimethate sodium
Trademarks: Alficetin (BMS); Colimicina (UCB); Colimycine (Sanofi-Aventis); Colomycin (Forest); Coly-Mycin M (Monarch); Methacolimycin (Kayaku); Promixin (Profile)
Molecular Formula: C58H105N16Na5O28S5
Molecular Weight: 1749.82
Percent Composition: C 39.81%, H 6.05%, N 12.81%, Na 6.57%, O 25.60%, S 9.16%
Properties: Prepd by treating colistin complex with formaldehyde and sodium bisulfite. Sol in water and stable in the dry form. LD50 i.v. in mice: >550 mg/kg (Barnett).
Toxicity data: LD50 i.v. in mice: >550 mg/kg (Barnett)
Derivative Type: Sulfate
CAS Registry Number: 1264-72-8
Trademarks: Belcomycine (Sanofi-Aventis); Colomycin (tabl.) (Forest)
Derivative Type: Colistin A
CAS Registry Number: 7722-44-3
CAS Name: Polymyxin E1
Molecular Formula: C53H100N16O13
Molecular Weight: 1169.46
Percent Composition: C 54.43%, H 8.62%, N 19.16%, O 17.79%
Properties: [a]225461 -93.3° (2% acetic acid).
Optical Rotation: [a]225461 -93.3° (2% acetic acid)
Derivative Type: Colistin B
CAS Registry Number: 7239-48-7
CAS Name: Polymyxin E2
Molecular Formula: C52H98N16O13
Molecular Weight: 1155.43
Percent Composition: C 54.05%, H 8.55%, N 19.40%, O 18.00%
Properties: [a]225461 -94.5° (2% acetic acid).
Optical Rotation: [a]225461 -94.5° (2% acetic acid)
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.
Collagenase Collinomycin Collinsonia Colloidal Bismuth Subcitrate Colocynthin

Colistin
Colistin.svg
Systematic (IUPAC) name
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
Clinical data
Trade names Coly-mycinm
Pregnancy cat. C
Legal status PoM (UK), not available in US
Routes topical, oral, intravenous, inhaled
Pharmacokinetic data
Bioavailability 0%
Half-life 5 hours
Identifiers
CAS number 1264-72-8 YesY
ATC code A07AA10 J01XB01 QJ51XB01
PubChem CID 5311054
DrugBank DB00803
ChemSpider 4470591 YesY
UNII WP15DXU577 N
KEGG D02138 YesY
ChEMBL CHEMBL501505 N
Chemical data
Formula C52H98N16O13 
Mol. mass 1155,4495 g/mol
 N (what is this?)  (verify)

Colistin (polymyxin E) is a polymyxin antibiotic produced by certain strains of Bacillus polymyxa var. colistinus. Colistin is a mixture of cyclic polypeptides colistin A and B. Colistin is effective against most Gram-negative bacilli and is used as a polypeptide antibiotic.

Colistin is a decades-old drug that fell out of favor due to its nephrotoxicity. It remains one of the last-resort antibiotics for multidrug-resistant Pseudomonas aeruginosa, Klebsiella pneumoniae, and Acinetobacter.[1] NDM-1 metallo-β-lactamase multidrug-resistant Enterobacteriaceae have also shown susceptibility to Colistin.[2]