Structural Formula Vector Image
Title: Narasin
CAS Registry Number: 55134-13-9
CAS Name: (4S)-4-Methylsalinomycin
Additional Names: narasin A
Manufacturers' Codes: Compd 79891; Antibiotic A-28086 factor A; C-7819B
Trademarks: Monteban (Elanco)
Molecular Formula: C43H72O11
Molecular Weight: 765.03
Percent Composition: C 67.51%, H 9.49%, O 23.00%
Literature References: Main component of a polyether antibiotic complex produced by Streptomyces aureofaciens NRRL 5758 & NRRL 8092. Production: D. H. Berg et al., DE 2525095 corresp to US 4038384 (1975, 1977 to Lilly); L. D. Boeck et al., Dev. Ind. Microbiol. 18, 471 (1976). Isoln and characterization: D. H. Berg, R. L. Hamill, J. Antibiot. 31, 1 (1978). Biosynthetic studies using 13C-NMR study: D. E. Dorman et al., Helv. Chim. Acta 59, 2625 (1976). Structure: J. L. Occolowitz et al., Biomed. Mass Spectrom. 3, 272 (1976); H. Seto et al., J. Antibiot. 30, 530 (1977). Anticoccidial activity: M. D. Ruff et al., Poult. Sci. 59, 2008 (1980). Total synthesis: Y. Kishi et al., Front. Chem., Plenary Keynote Lect. IUPAC Congr., 28th 1981, K. J. Laidler, Ed. (Pergamon, Oxford, 1982) pp 287-304. HPLC determn in animal feeds: M. R. LaPointe, H. Cohen, J. Assoc. Off. Anal. Chem. 71, 480 (1988).
Properties: Crystals from acetone-water, mp 98-100°; resolidif and remelts at 198-200°. uv max (ethanol): 285 nm (e 58). [a]D25 -54° (c = 0.2 in methanol). pKa 7.9 (80% aq DMF). Sol in alcohols, acetone, DMF, DMSO, benzene, chloroform, ethyl acetate. Insol in water. LD50 i.p. in mice: 7.15 mg/kg (Berg).
Melting point: mp 98-100°
pKa: pKa 7.9 (80% aq DMF)
Optical Rotation: [a]D25 -54° (c = 0.2 in methanol)
Absorption maximum: uv max (ethanol): 285 nm (e 58)
Toxicity data: LD50 i.p. in mice: 7.15 mg/kg (Berg)
Therap-Cat-Vet: Coccidiostat; growth stimulant.

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