1757. Capreomycin
Nomenclature
Description and references
Cyclic peptide antibiotic similar to viomycin; produced by Streptomyces capreolus NRRL 2773; Herr et al., 140th Am. Chem. Soc. Meet. (Chicago, Sept. 1961), Abstracts of Papers, p 49C; Chem. Eng. News 39, 57 (Sept. 18, 1961); GB 920563; US 3143468 (1963, 1964 both to Lilly). Mixture of capreomycins IA, IB, IIA, and IIB in the approx percentages, 25%, 67%, 3%, 6%, resp.: Herr, Redstone, Ann. N.Y. Acad. Sci. 135, 940 (1966). Activity studies: Sutton et al., ibid. 947; Lucchesi, Antibiot. Chemother. 16, 27 (1970). Proposed structure: Bycroft et al., Nature 231, 301 (1971). Revised structure and total synthesis: T. Shiba et al., Tetrahedron Lett. 1976, 3907; S. Nomoto et al., Tetrahedron 34, 921 (1978). Structure of IA and IB: eidem, J. Antibiot. 30, 955 (1977). Toxicity study: Welles et al., Ann. N.Y. Acad. Sci. 135, 960 (1966).
Properties
The mixture is a white solid. Sol in water. Practically insol in most organic solvents. pKa in 66% aq DMF: 6.2, 8.2, 10.1, 13.3. Stable in aq soln at pH 4-8; unstable in strongly acidic or strongly basic solns.Derivative
Disulfate.Nomenclature
Properties
Solubility data: March, Weiss, J. Assoc. Off. Anal. Chem. 50, 457 (1967). LD50 in mice, rats (mg/kg): 250, 325 i.v.; 514, 1191 s.c. (Welles).Derivative
Capreomycin IA.Nomenclature
Properties
mp 246-248° (dec). [α]D22 -21.9° (c = 0.5 in water). uv max (0.1N HCl): 269 nm (ε 24000); (H2O): 268 nm (ε 23900); (0.1N NaOH): 287 nm (ε 15900) (all for hydrochloride ethanolate).Derivative
Capreomycin IB.Nomenclature
Properties
mp 253-255° (dec). [α]D22 -44.6° (c = 0.5 in water). uv max (0.1N HCl): 268 nm (ε 22700); (H2O): 268 nm (ε 22300); (0.1N NaOH): 290 nm (ε 14400) (all for hydrochloride ethanolate).Note
Capreomycin IIA, capreomycin IIB. Structures corresp to capreomycins IA and IB but lack β-lysine residues.Therapeutic Category
Antibacterial (tuberculostatic).
Keywords
Antibacterial (Antibiotics); Polypeptides; Antibacterial (Tuberculostatic)