Meclocycline
Title: Meclocycline
CAS Registry Number: 2013-58-3
CAS Name: [4S-(4a,4aa,5a,5aa,12aa)]-7-Chloro-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: 7-chloro-6-methylene-5-hydroxytetracycline
Manufacturers' Codes: GS-2989; NSC-78502
Molecular Formula: C22H21ClN2O8
Molecular Weight: 476.86
Percent Composition: C 55.41%, H 4.44%, Cl 7.43%, N 5.87%, O 26.84%
Literature References: Semi-synthetic antibiotic derived from tetracycline, q.v. Prepn: R. K. Blackwood et al., US 2984686 (1961 to Pfizer); eidem, J. Am. Chem. Soc. 83, 2773 (1961); of the free base and 5-sulfosalicylate salt: eidem, ibid. 85, 3943 (1963). In vitro study: L. Lucca, G. Vittadini, G. Ital. Chemioter. 26, 203 (1979). 13C-NMR study: E. Mazzola et al., J. Pharm. Sci. 69, 229 (1980). Toxicity study: F. Bernardi et al., G. Ital. Chemioter. 17, 276 (1970).
Properties: uv max (methanol, 0.01N HCl): 245, 347 nm (log e 4.34, 410). LD50 in mice (mg/kg): >5000 orally, 425 i.p. (Bernardi).
Absorption maximum: uv max (methanol, 0.01N HCl): 245, 347 nm (log e 4.34, 410)
Toxicity data: LD50 in mice (mg/kg): >5000 orally, 425 i.p. (Bernardi)
 
Derivative Type: 5-Sulfosalicylate
CAS Registry Number: 73816-42-9
Trademarks: Meclan (Ortho); Mecloderm; Meclosorb (Basotherm); Meclutin (ABC); Traumatociclina (Biomed. Foscama)
Molecular Formula: C29H27ClN2O14S
Molecular Weight: 695.05
Percent Composition: C 50.11%, H 3.92%, Cl 5.10%, N 4.03%, O 32.23%, S 4.61%
Properties: uv max (methanol, 0.01N HCl): 239, 268, 346 nm (log e 4.46, 4.07, 4.11).
Absorption maximum: uv max (methanol, 0.01N HCl): 239, 268, 346 nm (log e 4.46, 4.07, 4.11)
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Tetracyclines.

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