Title: Maduramicin
CAS Registry Number: 84878-61-5
CAS Name: (2
R,3
S,4
S,5
R,6
S)-6-[(1
R)-1-[(2
S,5
R,7
S,8
R,9
S)-2-[(2
S,2¢
R,3¢
S,5
R,5¢
R)-3¢-[(2,6-Dideoxy-3,4-di-
O-methyl-b-L-
arabino-hexopyranosyl)oxy]octahydro-2-methyl-5¢-[(2
S,3
S,5
R,6
S)-tetrahydro-6-hydroxy-3,5,6-trimethyl-2
H-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-2
H-pyran-2-acetic acid, monoammonium salt
Synonyms: 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.