Title: Josamycin
CAS Registry Number: 16846-24-5
CAS Name: Leucomycin V 3-acetate 4B-(3-methylbutanoate)
Additional Names: leucomycin A3
Manufacturers' Codes: EN-141
Trademarks: Iosalide (Schering); Jomybel (Sarva); Josamina (Novag)
Molecular Formula: C42H69NO15
Molecular Weight: 827.99
Percent Composition: C 60.92%, H 8.40%, N 1.69%, O 28.98%
Literature References: Macrolide antibiotic produced by Streptomyces narbonensis var. josamyceticus nov. var. Isoln and characterization: T. Osono et al., J. Antibiot. 20A, 174 (1967). Manuf process: H. Umezawa,T. Osono, JP 66 21759 (1966 to Microbiochemical Res. Found.), C.A. 66, 54258w (1967). Prepn: Y. Oka et al., JP Kokai 76 41497 (1976 to Yamanouchi), C.A. 85, 121788b (1976). Identification with leucomycin A3: S. Omura et al., J. Antibiot. 23, 511 (1970). Structure: eidem, ibid. 27, 366 (1974). Absolute configuration: A. Ducruix et al., Chem. Commun. 1976, 947. Stereospecific total synthesis: K. Tatsuta et al., Tetrahedron Lett. 1980, 2837. Retrosynthetic studies: K. C. Nicolaou et al., J. Am. Chem. Soc. 103, 1222 (1981). A 17-membered aglycone was proposed at one time, see T. Osono, H. Umezawa in Drug Action and Drug Resistance in Bacteria 1, S. Mitsuhashi, Ed. (University Park Press, Baltimore, 1971) pp 41-120; T. Osono et al., J. Antibiot. 27, 366 (1974). Pharmacology: K. Kuriaki et al., Jpn. J. Antibiot. 22, 232 (1969). Review: T. Osono, H. Umezawa, loc. cit.
Properties: Colorless needles from benzene, mp 130-133° (after drying under reduced pressure at 100° for 5 hrs). [a]D25 -70° (c = 1 in ethanol). uv max (0.001N HCl): 232 nm (E1%1cm 325). pKa 7.1 (40% aq methanol). Very sol in methanol, ethanol, acetone, chloroform, ethyl acetate, dioxane, acidic water. Sol in butanol, ether, CCl4, benzene, toluene. Practically insol in water, petr ether, ligroin, n-hexane.
Melting point: mp 130-133° (after drying under reduced pressure at 100° for 5 hrs)
pKa: pKa 7.1 (40% aq methanol)
Optical Rotation: [a]D25 -70° (c = 1 in ethanol)
Absorption maximum: uv max (0.001N HCl): 232 nm (E1%1cm 325)
Derivative Type: Propionate
CAS Registry Number: 51016-68-3
Trademarks: Josacine (Bellon); Josamy (Yamanouchi); Josaxin (Boots); Wilprafen (Mack, Illert.)
Molecular Formula: C45H73NO16
Molecular Weight: 884.06
Percent Composition: C 61.14%, H 8.32%, N 1.58%, O 28.96%
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Macrolides. |