12-03755. Etamycin [Archived]
Nomenclature
Description and references
Monocyclic peptide lactone antibiotic produced by Streptomyces griseus and allied Streptomyces spp., which shows activity vs gram positive bacteria, Mycobacterium tuberculosis and some fungi. Obtained together with griseoviridin. Production and isoln: B. Heinemann et al., Antibiot. Annu. 1954-55, 728; Q. R. Bartz et al., ibid. 777. Pharmacology: H. L. Dickison et al., ibid. 733. Chemical studies: T. H. Haskell et al., ibid. 784. Biological studies: J. Ehrlich et al., ibid. 790. Structure: Sheehan et al., J. Am. Chem. Soc. 80, 3349 (1958). Confirmation of structure: Arnold et al., J. Chem. Soc. 1958, 4466. Prodn with griseoviridin: Q. R. Bartz et al., US 3023204 (1962 to Parke, Davis). Total synthesis: Sheehan, Ledis, J. Am. Chem. Soc. 95, 875 (1973). Mode of action: Garcia-Mendoza, Biochim. Biophys. Acta 97, 94 (1965). Mass spectra data: Rozynov et al., Zh. Obshch. Khim. 39, 891 (1969). Prodn of congeners by S. griseoviridus: C. Chopra et al., J. Antibiot. 32, 392 (1979). Biosynthetic studies of neoviridogriseins, homologs of etamycin: Y. Akumura et al., ibid. 575, 1002, 1130.
Properties
Weakly basic polypeptide, dec 168-170°. [α]D26 +62°, +31° (c = 5 in chloroform, alc). uv max (alc): 304.5 nm (log ε 3.91). pKa about 1 to 2. Soly in water about 1 mg/ml. Also sol in 1.0N HCl and 1.0N NaOH, in the lower alcohols and ketones, benzene, chloroform, carbon tetrachloride, carbon disulfide, ethyl acetate, peanut oil, ether. Practically insol in petr ether. LD50 in mice (mg/kg): >3000 orally, >2000 s.c., 273 i.p., 36-39 i.v. (Dickison).Derivative
Hydrochloride.Properties
Crystals, mp 163-170° (some dec). uv max: 304 nm (E1%1cm 86), after addition of alkali: 335 nm (E1%1cm 82). Soly in water about 4 mg/ml. Sol in methanol, ethanol, formamide. Slightly sol in acetone, ethyl acetate, or less polar solvents.Status
This monograph has been retired and is no longer subject to revision or update.