Capreomycin
Title: Capreomycin
CAS Registry Number: 11003-38-6
Trademarks: Capastat (Lilly)
Literature 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.
pKa: pKa in 66% aq DMF: 6.2, 8.2, 10.1, 13.3
 
Derivative Type: Disulfate
CAS Registry Number: 1405-36-3
Trademarks: Caprocin (Lilly); Ogostal (Lilly)
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).
Toxicity data: LD50 in mice, rats (mg/kg): 250, 325 i.v.; 514, 1191 s.c. (Welles)
 
Derivative Type: Capreomycin IA
CAS Registry Number: 37280-35-6
Molecular Formula: C25H44N14O8
Molecular Weight: 668.71
Percent Composition: C 44.90%, H 6.63%, N 29.32%, O 19.14%
Properties: mp 246-248° (dec). [a]D22 -21.9° (c = 0.5 in water). uv max (0.1N HCl): 269 nm (e 24000); (H2O): 268 nm (e 23900); (0.1N NaOH): 287 nm (e 15900) (all for hydrochloride ethanolate).
Melting point: mp 246-248° (dec)
Optical Rotation: [a]D22 -21.9° (c = 0.5 in water)
Absorption maximum: uv max (0.1N HCl): 269 nm (e 24000)
 
Derivative Type: Capreomycin IB
CAS Registry Number: 33490-33-4
Molecular Formula: C25H44N14O7
Molecular Weight: 652.71
Percent Composition: C 46.00%, H 6.79%, N 30.04%, O 17.16%
Properties: mp 253-255° (dec). [a]D22 -44.6° (c = 0.5 in water). uv max (0.1N HCl): 268 nm (e 22700); (H2O): 268 nm (e 22300); (0.1N NaOH): 290 nm (e 14400) (all for hydrochloride ethanolate).
Melting point: mp 253-255° (dec)
Optical Rotation: [a]D22 -44.6° (c = 0.5 in water)
Absorption maximum: uv max (0.1N HCl): 268 nm (e 22700)
 
NOTE: Capreomycin IIA, capreomycin IIB. Structures corresp to capreomycins IA and IB but lack b-lysine residues.
Therap-Cat: Antibacterial (tuberculostatic).
Keywords: Antibacterial (Antibiotics); Polypeptides; Antibacterial (Tuberculostatic).

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