Maduramicin
Title: Maduramicin
CAS Registry Number: 84878-61-5
CAS Name: (2R,3S,4S,5R,6S)-6-[(1R)-1-[(2S,5R,7S,8R,9S)-2-[(2S,2¢R,3¢S,5R,5¢R)-3¢-[(2,6-Dideoxy-3,4-di-O-methyl-b-L-arabino-hexopyranosyl)oxy]octahydro-2-methyl-5¢-[(2S,3S,5R,6S)-tetrahydro-6-hydroxy-3,5,6-trimethyl-2H-pyran-2-yl][2,2¢-bifuran]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]dec-7-yl]ethyl]tetrahydro-2-hydroxy-4,5-dimethoxy-3-methyl-2H-pyran-2-acetic acid, monoammonium salt
Additional Names: antibiotic X-14868A ammonium salt
Manufacturers' Codes: CL-273703
Trademarks: Cygro (Am. Cyanamid)
Molecular Formula: C47H83NO17
Molecular Weight: 934.16
Percent Composition: C 60.43%, H 8.96%, N 1.50%, O 29.12%
Literature References: Polyether antibiotic chemically related to the lonomycins, q.v. Isoln as sodium salt from Nocardia sp X-14868 and biological activity: C.-M. Liu et al., US 4278663 (1981 to Hoffmann-La Roche); as free acid hydrate from Actinomadura yumaense sp nov.: D. P. Labeda et al., US 4407946 (1983 to Am. Cyanamid). Fermentation and properties: C.-M. Liu et al., J. Antibiot. 36, 343 (1983). 13C-NMR spectrum: S. Rajan, ibid. 37, 1495 (1984). Biosynthetic studies: H.-R. Tsou et al., ibid. 1651; H.-R. Tsou et al., ibid. 40, 94 (1987). Antimalarial activity: L. Oronsky, US 4496549 (1985 to Am. Cyanamid). Nematocidal activity: I. B. Wood, US 4510134 (1985 to Am. Cyanamid).
 
Derivative Type: Sodium salt
Molecular Formula: C47H79NaO17
Molecular Weight: 939.11
Percent Composition: C 60.11%, H 8.48%, Na 2.45%, O 28.96%
Properties: Crystals from ethyl acetate + n-hexane, mp 193-195°. [a]D +40.6° (chloroform). [a]D +23.8° (methanol).
Melting point: mp 193-195°
Optical Rotation: [a]D +40.6° (chloroform); [a]D +23.8° (methanol)
 
NOTE: Not to be confused with maduramycin isolated from Actinomadura rubra, C28H22O10: W. F. Fleck et al., 16th Interscience Conference on Antimicrob. Ag. Chemother., Chicago, 1976, Abstracts of Papers, no. 51.
Therap-Cat-Vet: Coccidiostat.

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