2479. Colistin

Nomenclature

CAS number: 1066-17-7
Polymyxin E.

Description and 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., Chromatographia 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. Agents 25, 11-25 (2005).

Chemical structure

Derivative

Colistin sodium methanesulfonate.

Nomenclature

CAS number: 8068-28-8
Colistimethate sodium; Alficetin (BMS); Colimicina (UCB); Colimycine (Sanofi-Aventis); Colomycin (Forest); Coly-Mycin M (Monarch); Methacolimycin (Kayaku); Promixin (Profile).
C58H105N16Na5O28S5; mol wt 1749.82.
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).

Derivative

Sulfate.

Nomenclature

CAS number: 1264-72-8
Belcomycine (Sanofi-Aventis); Colomycin (tabl.) (Forest).

Derivative

Colistin A.

Nomenclature

CAS number: 7722-44-3
Polymyxin E1.
C53H100N16O13; mol wt 1169.46.
C 54.43%, H 8.62%, N 19.16%, O 17.79%.

Properties

[α]225461 -93.3° (2% acetic acid).

Derivative

Colistin B.

Nomenclature

CAS number: 7239-48-7
Polymyxin E2.
C52H98N16O13; mol wt 1155.43.
C 54.05%, H 8.55%, N 19.40%, O 18.00%.

Properties

[α]225461 -94.5° (2% acetic acid).

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); Polypeptides