7573. Polymyxin

Nomenclature

CAS number: 1406-11-7

Description and references

Antibiotic complex produced by Bacillus polymyxa: Brownlee, Jones, Biochem. J. 43, XXV (1948). Prepn: Ainsworth, Pope, US 2565057 (1951 to Burroughs Wellcome); Petty, US 2595605 (1952 to Am. Cyanamid); Benedict, Stodola, US 2771397 (1956 to USDA). Purification: Hastings et al., GB 782926 (1957 to Distillers Co.). Polymyxins A, B, C, D, E, F, K, M, P, S and T have been identified. Isoln of polymyxins A, B, C and E: Few, Schulman, Biochem. J. 54, 171 (1953); of polymyxin D: Stansley et al., Bull. Johns Hopkins Hosp. 81, 43 (1947); of polymyxin F: W. L. Parker et al, J. Antibiot. 30, 767 (1977); of polymyxin K: Kimura, JP 71 16152 (1971), C.A. 75, 62180r (1971); of polymyxin M: Khokhlov et al., C.A. 55, 5653h (1961); of polymyxin P: Kimura et al., J. Antibiot. 22, 449 (1969); of polymyxin S1 and polymyxin T1: J. Shoji et al., ibid. 30, 1029 (1977). Resolution of polymyxin B into B1 and B2: Hausmann, Craig, J. Am. Chem. Soc. 76, 4892 (1954). Structure and synthesis of polymyxin B1: Wilkinson, Lowe, Nature 202, 1211 (1964); Vogler et al., Helv. Chim. Acta 48, 1161 (1965). Structure of polymyxin B2: Wilkinson, Lowe, Nature 204, 993 (1964). Separation of polymyxin D into D1 and D2 and structures: Hayashi et al., Experientia 22, 354 (1966). Structure of polymyxin S1: J. Shoji et al., J. Antibiot. 30, 1035 (1977); of polymyxin T1: eidem, ibid. 1042. Review: Vogler, Studer, Experientia 22, 345-354 (1966); Paulus, “Polymyxins” in Antibiotics II, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 254-267.

Chemical structure

Properties

Obtained as the hydrochloride. Nearly colorless powder, dec 228-230°. [α]D23 -40° (c = 1.05). The hydrochloride is very sol (more than 40%) in water and methanol. The soly decreases in the higher alcs. Practically insol in the usual ethers, esters, ketones, hydrocarbons, and the chlorinated solvents. Forms water insol salts with a number of ppts such as picric acid, helianthic acid, Reinecke salt. The free base is slightly sol in water; almost insol in alc.

Derivative

Polymyxin B.

Nomenclature

CAS number: 1404-26-8

Properties

Mixture of polymyxins B1 and B2. [α]5461 -106.3° (1N HCl).

Derivative

Polymyxin B sulfate.

Nomenclature

CAS number: 1405-20-5
Aerosporin (Burroughs Wellcome); Mastimyxin (Chassot).

Description and references

Solubilities: Weiss et al., Antibiot. Chemother. 7, 374 (1957).

Derivative

Polymyxin B sulfate mixture with trimethoprim.

Nomenclature

Polytrim (Wellcome).

Derivative

Polymyxin B1.

Nomenclature

CAS number: 4135-11-9
C56H98N16O13; mol wt 1203.48.
C 55.89%, H 8.21%, N 18.62%, O 17.28%.

Derivative

Polymyxin B1 pentahydrochloride.
C56H98N16O13.5HCl; mol wt 1385.78.
C 48.54%, H 7.49%, N 16.17%, O 15.01%, Cl 12.79%.

Properties

White powder. [α]D25 -85.11° (c = 2.33 in 75% ethanol).

Derivative

Polymyxin B2.

Nomenclature

CAS number: 34503-87-2
C55H96N16O13; mol wt 1189.45.
C 55.54%, H 8.14%, N 18.84%, O 17.49%.

Properties

[α]225461 -112.4° (2% Acetic acid).

Derivative

Polymyxin D1.

Nomenclature

CAS number: 10072-50-1
C50H93N15O15; mol wt 1144.36.
C 52.48%, H 8.19%, N 18.36%, O 20.97%.

Derivative

Polymyxin D2.

Nomenclature

CAS number: 34167-45-8
C49H91N15O15; mol wt 1130.34.
C 52.07%, H 8.11%, N 18.59%, O 21.23%.

Derivative

Polymyxin E see Colistin.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); Polypeptides