Title: Dirithromycin
CAS Registry Number: 62013-04-1
CAS Name: (1
R,2
R,3
R,6
R,7
S,8
S,9
R,10
R,12
R,13
S,15
R,17
S)-7-[(2,6-Dideoxy-3-
C-methyl-3-
O-methyl-a-L-
ribo-hexopyranosyl)oxy]-3-ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-9-[[3,4,6-trideoxy-3-(dimethylamino)-b-D-
xylo-hexopyranosyl]oxy]-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
Synonyms: [9
S(
R)]-9-deoxo-11-deoxy-9,11-[imino[2-(2-methoxyethoxy)ethylidene]oxy]erythromycin
Manufacturers' Codes: LY-237216; AS-E 136
Trademarks: Dynabac (Lilly); Noriclan (Lilly); Nortron (Lilly); Valodin (Ferrer)
Molecular Formula: C42H78N2O14
Molecular Weight: 835.07
Percent Composition: C 60.41%, H 9.41%, N 3.35%, O 26.82%
Literature References: Semi-synthetic derivative of erythromycin,
q.v. Prepn:
BE 840431 (1976 to Thomae); R. Maier
et al., US 4048306 (1977 to Boehringer, Ing.). Synthesis, 1H- and 13C-NMR, and antimicrobial evaluation: F. T. Counter
et al., Antimicrob. Agents Chemother. 35, 1116 (1991). X-ray structure determn: P. Luger, R. Maier,
J. Cryst. Mol. Struct. 9, 329 (1979). HPLC determn in plasma: G. W. Whitaker, T. D. Lindstrom,
J. Liq. Chromatogr. 11, 3011 (1988). Symposium on antibacterial activity, pharmacology, and clinical experience:
J. Antimicrob. Chemother. 31, Suppl. C, 1-185 (1993).
Properties: Crystals from ethanol/water, mp 186-189° (dec) (Counter). pKa 9.0 in 66% aq dimethyl fluoride. LD50 in mice (g/kg): >1 s.c.; >1 orally (Maier).
Melting point: mp 186-189° (dec) (Counter)
pKa: pKa 9.0 in 66% aq dimethyl fluoride
Toxicity data: LD50 in mice (g/kg): >1 s.c.; >1 orally (Maier)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Macrolides.