Primycin

Literature References: Macrolide antibiotic complex of more than 20 components produced by actinomycetes found in the intestinal tract of the wax moth (Galeria melonella). Nine primary components, in 3 major groups designated A, B, and C, represent 90% of the total material. Originally thought to be a single entity which was subseqently identified as the major component, primycin A1. Isoln from cultures of Streptomyces primycini: Vályi-Nagy et al., Nature 174, 1105 (1954); HU 146332 and HU 151197 (1962, 1964 both to Hung. Acad. Sci.). Production by Thermopolyspora galeriensis (also designated Micromonospora galeriensis): T. Vályi-Nagy et al., HU 153593; eidem, US 3498884 (1967, 1970 both to Chinoin). Structure of A1: J. Aberhart et al., J. Am. Chem. Soc. 92, 5816 (1970); eidem, J. Chem. Soc. Perkin Trans. 1 1974, 816, 836. TLC sepn of components: I. Szilagyi et al., J. Chromatogr. 295, 141 (1984). Structures of the nine primary components: J. Frank et al., Tetrahedron Lett. 28, 2759 (1987). Antibacterial activity and toxicity: T. Vályi-Nagy et al., Pharmazie 11, 304 (1956). Antifungal activity in vitro: J. V. Uri, P. Actor, J. Antibiot. 32, 1207 (1979). Mode of action: I. Horvath et al., Arch. Microbiol. 121, 135 (1979). Clinical studies in dermatological infections: C. Mészáros, K. Vezekényi, Ther. Hung. 35, 77 (1987); J. Biro, V. Várkonyi, ibid. 136; G. Bálint, ibid. 140. Review: J. V. Uri, Acta Microbiol. Hung. 33, 141 (1986).

Properties: mp 192-195° (dec) (Aberhart, 1974); also reported as 202-206° (dec) (Uri, 1986). Infrared and ultraviolet spectra: Szilágyi et al., Nature 193, 243 (1962). Fairly soluble in methanol (2.5%), less sol in the higher alcohols, sparingly sol in pyridine, glacial acetic acid, water. LD50 in mice, guinea pigs, rats, rabbits (mg/kg): 2.5, 5.0, 10.0, 10.0 i.p. (Vályi-Nagy, 1956).