Structural Formula Vector Image
Title: Avilamycin
CAS Registry Number: 11051-71-1
Manufacturers' Codes: LY-048740
Trademarks: Maxus (Elanco); Surmax (Elanco)
Literature References: Polyether antibiotic complex produced by Streptomyces viridochromogenes, ETH 23575 (NRRL 2860); belongs to the orthosomycin family of antibiotics, members of which contain one or more ortho ester linkages associated with carbohydrate residues. Isoln: E. Gaeumann et al., DE 1116864; eidem, US 3131126 (1961, 1964 both to Ciba-Geigy); and characterization: F. Buzzetti et al., Experientia 24, 320 (1968). Mechanism of action studies: H. Wolf, FEBS Lett. 36, 181 (1973). Avilamycin A is the main component; avilamycins B through N are also known and are derivatives of A differing at the C-45 linkage and/or the C-56 ketone adduct. Isoln of avilamycin C: W. Heilman et al., Helv. Chim. Acta 62, 1 (1979). Structural study of A and C: eidem, ibid.; W. Keller-Schierlein et al., ibid. 7; E. Kupfer et al., ibid. 65, 3 (1982). Isoln and structure of avilamycins F through N: J. L. Mertz et al., J. Antibiot. 39, 877 (1986). GC determn of avilamycin residues in swine tissue and fluids: G. Formica, C. Giannone, J. Assoc. Off. Anal. Chem. 69, 763 (1986). Synthesis of the A-B fragment of avilamycins A and C: P. Jütten et al., Tetrahedron 43, 4133 (1987); of the disaccharide C-D fragment: J.-M. Beau et al., Tetrahedron Lett. 28, 1105 (1987). Use as a feed additive: F. Knusel et al., US 4185091 (1980 to Ciba-Geigy); in prevention of swine dysentery: E. E. Ose, US 4436734 (1984 to Lilly). Effect on feed conversion efficiency in swine: D. J. Jones et al., J. Anim. Sci. 65, 881 (1987). Metabolism in swine: J. D. Magnussen et al., J. Agric. Food Chem. 39, 306 (1991).
Properties: Colorless, needle-shaped crystals from acetone/ether, mp 188-189.5°. [a]D20 +0.8° (c = 1.165 in abs ethanol) and -7.7° (c = 1.083 in chloroform).
Melting point: mp 188-189.5°
Optical Rotation: [a]D20 +0.8° (c = 1.165 in abs ethanol) and -7.7° (c = 1.083 in chloroform)
Derivative Type: Avilamycin A
Molecular Formula: C61H88Cl2O32
Molecular Weight: 1404.24
Percent Composition: C 52.17%, H 6.32%, Cl 5.05%, O 36.46%
Properties: Colorless needles from chloroform/petr ether, mp 181-182° (1-2.H2O). uv max (methanol): 227, 286 nm (log e 4.15, 3.33).
Melting point: mp 181-182° (1-2.H2O)
Absorption maximum: uv max (methanol): 227, 286 nm (log e 4.15, 3.33)
Derivative Type: Avilamycin C
Molecular Formula: C61H90Cl2O32
Molecular Weight: 1406.25
Percent Composition: C 52.10%, H 6.45%, Cl 5.04%, O 36.41%
Properties: Dihydrate, colorless fine plates from acetone/ether, mp 188-189°. [a]D20 -4.8° (c = 1.44 in chloroform). uv max (methanol): 228, 284 nm (log e 4.12, 3.33).
Melting point: mp 188-189°
Optical Rotation: [a]D20 -4.8° (c = 1.44 in chloroform)
Absorption maximum: uv max (methanol): 228, 284 nm (log e 4.12, 3.33)
Therap-Cat-Vet: Growth promotant.

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