Polymyxin
Title: Polymyxin
CAS Registry Number: 1406-11-7
Literature 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.
Properties: Obtained as the hydrochloride. Nearly colorless powder, dec 228-230°. [a]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.
Optical Rotation: [a]D23 -40° (c = 1.05)
 
Derivative Type: Polymyxin B
CAS Registry Number: 1404-26-8
Properties: Mixture of polymyxins B1 and B2. [a]5461 -106.3° (1N HCl).
Optical Rotation: [a]5461 -106.3° (1N HCl)
 
Derivative Type: Polymyxin B sulfate
CAS Registry Number: 1405-20-5
Trademarks: Aerosporin (Burroughs Wellcome); Mastimyxin (Chassot)
Literature References: Solubilities: Weiss et al., Antibiot. Chemother. 7, 374 (1957).
 
Derivative Type: Polymyxin B sulfate mixture with trimethoprim
Trademarks: Polytrim (Wellcome)
 
Derivative Type: Polymyxin B1
CAS Registry Number: 4135-11-9
Molecular Formula: C56H98N16O13
Molecular Weight: 1203.48
Percent Composition: C 55.89%, H 8.21%, N 18.62%, O 17.28%
 
Derivative Type: Polymyxin B1 pentahydrochloride
Molecular Formula: C56H98N16O13.5HCl
Molecular Weight: 1385.78
Percent Composition: C 48.54%, H 7.49%, N 16.17%, O 15.01%, Cl 12.79%
Properties: White powder. [a]D25 -85.11° (c = 2.33 in 75% ethanol).
Optical Rotation: [a]D25 -85.11° (c = 2.33 in 75% ethanol)
 
Derivative Type: Polymyxin B2
CAS Registry Number: 34503-87-2
Molecular Formula: C55H96N16O13
Molecular Weight: 1189.45
Percent Composition: C 55.54%, H 8.14%, N 18.84%, O 17.49%
Properties: [a]225461 -112.4° (2% Acetic acid).
Optical Rotation: [a]225461 -112.4° (2% Acetic acid)
 
Derivative Type: Polymyxin D1
CAS Registry Number: 10072-50-1
Molecular Formula: C50H93N15O15
Molecular Weight: 1144.36
Percent Composition: C 52.48%, H 8.19%, N 18.36%, O 20.97%
 
Derivative Type: Polymyxin D2
CAS Registry Number: 34167-45-8
Molecular Formula: C49H91N15O15
Molecular Weight: 1130.34
Percent Composition: C 52.07%, H 8.11%, N 18.59%, O 21.23%
 
Derivative Type: Polymyxin E see Colistin
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.

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