Title: Myxin
CAS Registry Number: 13925-12-7
CAS Name: 6-Methoxy-1-phenazinol 5,10-dioxide
Additional Names: 1-hydroxy-6-methoxyphenazine 5,10-dioxide; 3C antibiotic
Molecular Formula: C13H10N2O4
Molecular Weight: 258.23
Percent Composition: C 60.47%, H 3.90%, N 10.85%, O 24.78%
Literature References: Potent broad-spectrum antibiotic capable of inhibiting a wide range of gram-positive and gram-negative bacteria, various fungi and yeasts. Isoln from a Sorangium species (strain 3C), a soil-borne myxobacter: Peterson et al., Can. J. Microbiol. 12, 221 (1966). Proposed structure: Edwards, Gillespie, Tetrahedron Lett. 1966, 4867. Revised structure and synthesis: Weigele, Leimgruber, ibid. 1967, 715; Sigg, Toth, Helv. Chim. Acta 50, 716 (1967). Activity: E. Grunberg et al., Chemotherapia 12, 272 (1967). Crystal structure: Hanson, Acta Crystallogr. B24, 1084 (1968). Review: Edwards, Gillespie, Proc. Int. Symp. Drug Res. 1967, 236; Leimgruber, Grunberg, ibid. 240; Baker, Vezina, ibid. 242.
Properties: Red needles from acetone, mp 120-130°; also reported as mp 149° (dec) (Sigg, Toth). Strongly exothermic at 149°. May explode on drying with heat: Rachlin, Chem. Eng. News 45, 32 (Sept. 4, 1967). uv max (0.1 N HCl): 283, 340 nm (e 97000, 5400); absorption max (0.1N HCl): 505 nm (e 6500). Stable in water after 6 hours at 37° in 0.05N acetate buffer at pH 5.0, in 0.05N phosphate at pH 6.0 and 7.0, or in 0.005N tris-HCl at pH 8.0 and 9.0. Stable at 70° except in phosphate buffer. Acetate, methanol, or aq tris buffer solns remain stable indefinitely at 4°. LD50 in mice (mg/kg): >2000 orally, >2000 s.c., 133 i.p. (Grunberg).
Melting point: mp 120-130°; mp 149° (dec) (Sigg, Toth)
Absorption maximum: uv max (0.1 N HCl): 283, 340 nm (e 97000, 5400); absorption max (0.1N HCl): 505 nm (e 6500)
Toxicity data: LD50 in mice (mg/kg): >2000 orally, >2000 s.c., 133 i.p. (Grunberg)
Derivative Type: Copper(II) complex
CAS Registry Number: 39238-36-3
Additional Names: Cuprimyxin
Manufacturers' Codes: Ro-7-4488/1
Trademarks: UNITOP (Roche)
Molecular Formula: C26H18CuN4O8
Molecular Weight: 577.99
Percent Composition: C 54.03%, H 3.14%, Cu 10.99%, N 9.69%, O 22.14%
Literature References: Prepn: W. Leimgruber et al., DE 1931466; eidem, US 3586674 (1970, 1971 both to Hoffmann-La Roche). Activity studies: Maestrone et al., Am. J. Vet. Res. 33, 185 (1972).
Properties: Dark green, fine crystals. uv max (DMSO): 287, 300, 356 nm (e 68500, 63200, 10000); absorption max (DMSO): 408, 610 nm (e 10400, 9500).
Absorption maximum: uv max (DMSO): 287, 300, 356 nm (e 68500, 63200, 10000); absorption max (DMSO): 408, 610 nm (e 10400, 9500)
Therap-Cat-Vet: Antibacterial, antifungal. |