Natamycin
Title: Natamycin
CAS Registry Number: 7681-93-8
CAS Name: Pimaricin
Additional Names: antibiotic A 5283; tennecetin
Manufacturers' Codes: CL-12625
Trademarks: Mycophyt (Mycofarm); Myprozine (Am. Cyanamid); Natacyn (Alcon); Pimafucin (Basotherm); Synogil (Basotherm)
Molecular Formula: C33H47NO13
Molecular Weight: 665.73
Percent Composition: C 59.54%, H 7.12%, N 2.10%, O 31.24%
Literature References: Polyene antifungal antibiotic produced by Streptomyces natalensis from soil near Pietermaritzburg, South Africa and by S. chattanoogensis. Isoln: Struyk et al., Antibiot. Annu. 1957-1958, 878. Prodn: GB 844289 (1960 to Koninklijke Nederlandsche Gist en Spiritus-Fabriek); GB 846933 (1960 to Am. Cyanamid). Identity with tennecetin: Divekar et al., Antibiot. Chemother. 11, 377 (1961). Structure: Golding et al., Tetrahedron Lett. 1966, 3551; Meyer, Chem. Commun. 1968, 470. Configuration: Gaudiano et al., Chim. Ind. (Milan) 48, 1327 (1966). Revised structure: R. C. Pandey, K. L. Rinehart, J. Antibiot. 29, 1035 (1976). Soly data: Marsh, Weiss, J. Assoc. Off. Anal. Chem. 50, 457 (1967). Toxicology: G. J. Levinskas et al., Toxicol. Appl. Pharmacol. 8, 97 (1966). Comprehensive description: H. Brik, Anal. Profiles Drug Subs. Excip. 23, 399-419 (1994).
Properties: Crystals from methanol + water, darkens ~200°, dec 280-300°. [a]D20 +278° (c = 1 in CH3COOH). Sensitive to light, but otherwise very stable in the dry state. uv max (methanol + 0.1% CH3COOH): 220, 280, 290, 303, 318 nm (e 21300, 26630, 52930, 83220, 76230). Soly at 20° (g/ml): 87% glycerol 0.18. Practically insol in higher alcohols, ether, esters, aromatic or aliphatic hydrocarbons, chlorinated hydrocarbons, ketones, dioxane, cyclohexanol, oils. LD50 orally in male, female rats (g/kg): 2.73, 4.67 (Levinskas).
Optical Rotation: [a]D20 +278° (c = 1 in CH3COOH)
Absorption maximum: uv max (methanol + 0.1% CH3COOH): 220, 280, 290, 303, 318 nm (e 21300, 26630, 52930, 83220, 76230)
Toxicity data: LD50 orally in male, female rats (g/kg): 2.73, 4.67 (Levinskas)
Therap-Cat: Antifungal (topical).
Keywords: Antifungal (Antibiotics); Polyenes.

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