Title: Methacycline
CAS Registry Number: 914-00-1
CAS Name: [4S-(4a,4aa,5a,5aa,12aa)]-4-Dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide
Additional Names: 6-methyleneoxytetracycline; 6-methylene-5-hydroxytetracycline; metacycline
Molecular Formula: C22H22N2O8
Molecular Weight: 442.42
Percent Composition: C 59.73%, H 5.01%, N 6.33%, O 28.93%
Literature References: Broad spectrum, semi-synthetic antibiotic related to tetracycline, q.v. Prepn from oxytetracycline, q.v.: R. K. Blackwood et al., US 2984686 (1961 to Pfizer); eidem, J. Am. Chem. Soc. 83, 2773 (1961); 85, 3943 (1963). Solubility data: J. R. Marsh, P. J. Weiss, J. Assoc. Off. Anal. Chem. 50, 257 (1967). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Comparative clinical study with ampicillin, q.v., in chronic bronchitis: S. Chodosh et al., Chest 69, 587 (1976).
Derivative Type: Hydrochloride
CAS Registry Number: 3963-95-9
Trademarks: Adriamicina (Farmochim. Ital.); Ciclobiotic (Beta); Germiciclin (Mendelejeff); Metadomus (Med. Domus); Metilenbiotic (Coli); Londomycin; Optimycin (Novartis); Physiomycine; Rindex (Sidus); Rondomycin (Wallace)
Molecular Formula: C22H22N2O8.HCl
Molecular Weight: 478.88
Percent Composition: C 55.18%, H 4.84%, N 5.85%, O 26.73%, Cl 7.40%
Properties: Obtained as crystals containing 0.5 mol water and 0.5 mol methanol from methanol + acetone + concd HCl + ether. Yellow, crystalline powder, dec ~205°. Bitter taste. Soluble in water, sparingly sol in alcohol. Practically insol in ether, chloroform. uv max (methanol + 0.01N HCl): 253, 345 nm (log e 4.37, 4.19). LD50 in rats, mice (mg/kg): 252, 288 i.p. (Goldenthal).
Absorption maximum: uv max (methanol + 0.01N HCl): 253, 345 nm (log e 4.37, 4.19)
Toxicity data: LD50 in rats, mice (mg/kg): 252, 288 i.p. (Goldenthal)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Tetracyclines.

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