Title: Viomycin
CAS Registry Number: 32988-50-4
Additional Names: Celiomycin; florimycin; tuberactinomycin B
Molecular Formula: C25H43N13O10
Molecular Weight: 685.69
Percent Composition: C 43.79%, H 6.32%, N 26.56%, O 23.33%
Literature References: Polypeptide antibiotic produced by various Streptomyces species including S. puniceus, S. floridae, S. vinaceus. Isoln: A. C. Finlay et al., Am. Rev. Tuberc. 63, 1 (1951); Bartz et al., ibid. 4. Production: Marsh et al., US 2633445 (1953 to Ciba); Freaney, US 2828245 (1958 to C.S.C.). Purification and chemical characterization: T. Kitagawa et al., Chem. Pharm. Bull. 20, 2176 (1972). Proposed structure: Yoshioka et al., Tetrahedron Lett. 1971, 2043. Alternate structure: B. W. Bycroft et al., ibid. 1968, 5901; eidem, Experientia 27, 501 (1971); eidem, J. Chem. Soc. Perkin Trans. 1 1972, 820, 827. Confirmed structure: Noda et al., J. Antibiot. 25, 427 (1972); T. Kitagawa et al., Chem. Pharm. Bull. 20, 2215 (1972). X-ray crystallography: B. W. Bycroft, Chem. Commun. 1972, 660. Biosynthesis: J. H. Carter II et al., Biochemistry 13, 1221, 1227 (1974). Toxicological study: H. Keller et al., Arzneim.-Forsch. 6, 61 (1956). Enzyme immunoassay for determn in body fluids: T. Kitagawa et al., Chem. Pharm. Bull. 30, 2487 (1982).
Derivative Type: Sulfate
CAS Registry Number: 37883-00-4
Trademarks: Viocin (Pfizer)
Properties: Hygroscopic plates, mp 266° (dec). [a]D18 -29.5° (c = 1 in H2O). uv max (water or 0.1N HCl; 0.1N NaOH): 268 nm (log e 4.4); 285 nm (log e 4.2). LD50 in mice (mg/kg): 240 i.v. (Finlay); 1750 s.c. (Keller). Sol in water. Relatively insol in most organic solvents. Solns adjusted to pH 5-6 are quite stable. Soly data: Weiss et al., Antibiot. Chemother. 7, 374 (1957).
Melting point: mp 266° (dec)
Optical Rotation: [a]D18 -29.5° (c = 1 in H2O)
Absorption maximum: uv max (water or 0.1N HCl; 0.1N NaOH): 268 nm (log e 4.4); 285 nm (log e 4.2)
Toxicity data: LD50 in mice (mg/kg): 240 i.v. (Finlay); 1750 s.c. (Keller)
Derivative Type: Pantothenate sulfate
CAS Registry Number: 1401-79-2
Molecular Formula: C25H43N13O10.C9H17NO5.H2SO4
Molecular Weight: 1003.00
Percent Composition: C 40.71%, H 6.23%, N 19.55%, O 30.31%, S 3.20%
Literature References: Prepn: H. Keller, H. Mückter, DE 1011800 (1957 to Grünenthal), C.A. 53, 13519c (1959).
Properties: Crystals, mp 242° (dec).
Melting point: mp 242° (dec)
Derivative Type: Hydrochloride
Properties: Hygroscopic plates, mp 270° (dec). [a]D18 -16.6° (c = 1 in H2O). uv max (water; 0.1N HCl; 0.1N NaOH): 268 nm (log e 4.5); 268 nm (log e 4.4); 285 nm (log e 4.3).
Melting point: mp 270° (dec)
Optical Rotation: [a]D18 -16.6° (c = 1 in H2O)
Absorption maximum: uv max (water; 0.1N HCl; 0.1N NaOH): 268 nm (log e 4.5); 268 nm (log e 4.4); 285 nm (log e 4.3)
Therap-Cat: Antibacterial (tuberculostatic).
Keywords: Antibacterial (Antibiotics); Polypeptides; Antibacterial (Tuberculostatic). |