Rifamide
Title: Rifamide
CAS Registry Number: 2750-76-7
CAS Name: 4-O-[2-(Diethylamino)-2-oxoethyl]-rifamycin
Additional Names: 2-[(1,2-dihydro-5,6,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-9-yl)oxy]-N,N-diethylacetamide 21-acetate; N,N-diethylrifomycin B amide; rifamycin B diethylamide
Manufacturers' Codes: M-14
Trademarks: Rifocin M (Lepetit)
Molecular Formula: C43H58N2O13
Molecular Weight: 810.93
Percent Composition: C 63.69%, H 7.21%, N 3.45%, O 25.65%
Literature References: Prepn: BE 632770; Sensi, Maggi, US 3313804 (1963, 1967 both to Lepetit); Sensi et al., J. Med. Chem. 7, 596 (1964). Physical and chemical properties: Maggi et al., Farmaco Ed. Prat. 20, 147 (1965). Activity data: Pallanza et al., Arzneim.-Forsch. 15, 800 (1965); Monnier, Bourse, Pathol. Biol. 16, 901 (1968). Metabolic studies: Fürész et al., Arzneim.-Forsch. 15, 802 (1965); Maffii, Shiatti, Toxicol. Appl. Pharmacol. 8, 138 (1966). Toxicology: Dezulian et al., ibid. 126.
Properties: Yellow-orange ppt, crystallized from benzene + hexane. No definite mp, begins to soften at 140°, melts completely at 170° (dec). [a]D20 -48.7° (c = 0.4 in methanol). Absorption max in phosphate buffer (pH 7.38): 222, 302, 421 nm (e 42820, 20770, 16200). LD50 in mice, rats (mg/kg): 2450, >4000 orally; 640, 2500 s.c.; 320, 535 i.p.; 315, 380 i.v. (Dezulian).
Optical Rotation: [a]D20 -48.7° (c = 0.4 in methanol)
Absorption maximum: Absorption max in phosphate buffer (pH 7.38): 222, 302, 421 nm (e 42820, 20770, 16200)
Toxicity data: LD50 in mice, rats (mg/kg): 2450, >4000 orally; 640, 2500 s.c.; 320, 535 i.p.; 315, 380 i.v. (Dezulian)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Ansamycins.

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