Title: Clarithromycin
CAS Registry Number: 81103-11-9
CAS Name: 6-
O-Methylerythromycin
Manufacturers' Codes: A-56268; TE-031
Trademarks: Biaxin (Abbott); Clarosip (Grñenthal); Clathromycin (Taisho); Cyllind (Abbott); Klacid (Abbott); Klaricid (Abbott); Macladin (Guidotti); Naxy (Sanofi Winthrop); Veclam (Zambon); Zeclar (Abbott)
Molecular Formula: C38H69NO13
Molecular Weight: 747.95
Percent Composition: C 61.02%, H 9.30%, N 1.87%, O 27.81%
Literature References: Semisynthetic macrolide antibiotic; derivative of erythromycin,
q.v. Prepn: Y. Watanabe
et al., EP 41355;
eidem, US 4331803 (1981, 1982 both to Taisho); and
in vitro antibacterial activity: S. Morimoto
et al., J. Antibiot. 37, 187 (1984).
In vitro and
in vivo antibacterial activity: P. B. Fernandes
et al., Antimicrob. Agents Chemother. 30, 865 (1986). Comparative antibacterial spectrum
in vitro: C. Benson
et al., Eur. J. Clin. Microbiol. 6, 173 (1987); H. M. Wexler, S. M. Finegold,
ibid. 492. HPLC determn in biological fluids: D. Croteau
et al., J. Chromatogr. 419, 205 (1987); in plasma: H. Amini, A. Ahmadiani,
J. Chromatogr. B 817, 193 (2005). Acute toxicity study: S. Abe
et al., Chemotherapy (Tokyo) 36, Suppl. 3, 274 (1988). Symposium on pharmacology and comparative clinical studies:
J. Antimicrob. Chemother. 27, Suppl. A, 1-124 (1991). Comprehensive description: I. I. Salem,
Anal. Profiles Drug Subs. Excip. 24, 45-85, (1996).
Properties: Colorless needles from chloroform + diisopropyl ether (1:2), mp 217-220° (dec). Also reported as crystals from ethanol, mp 222-225° (Morimoto). uv max (CHCl3): 288 nm (e 27.9). uv max (CHCl3): 240, 288 nm; (methanol): 211, 288 nm. [a]D24 -90.4° (c = 1 in CHCl3). Stable at acidic pH. LD50 in male, female mice, male, female rats (mg/kg): 2740, 2700, 3470, 2700 orally, 1030, 850, 669, 753 i.p., >5000 all s.c. (Abe).
Melting point: mp 217-220° (dec); mp 222-225° (Morimoto)
Optical Rotation: [a]D24 -90.4° (c = 1 in CHCl3)
Absorption maximum: uv max (CHCl3): 288 nm (e 27.9). uv max (CHCl3): 240, 288 nm
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 2740, 2700, 3470, 2700 orally, 1030, 850, 669, 753 i.p., >5000 all s.c. (Abe)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Macrolides.
