2886. Demeclocycline
Nomenclature
CAS number: 127-33-3
[4S-(4α,4aα,5aα,6β,12aα)]-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide; 7-chloro-6-demethyltetracycline; demethylchlortetracycline (obsolete); RP-10192; Bioterciclin; Declomycin (Wyeth); Deganol; Ledermycin (Wyeth); Periciclina. C21H21ClN2O8; mol wt 464.85.
C 54.26%, H 4.55%, Cl 7.63%, N 6.03%, O 27.53%.
Description and references
Antibiotic related to tetracycline produced by Streptomyces aureofaciens. Prepn: McCormick et al., J. Am. Chem. Soc. 79, 4561 (1957); US 2878289 (1959 to Am. Cyanamid). Improved fermentation processes: Szumski, US 3012946; Goodman, Matrishin, US 3019172; Goodman, US 3050446 (1961, 1962, 1962 all to Am. Cyanamid); FR 1344645 (1963 to Merck & Co.); Neidleman, US 3154476 (1964 to Olin Mathieson). Abs config: Dobrynin et al., Tetrahedron Lett. 1962, 901. Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).
Derivative
Sesquihydrate.Properties
mp 174-178° (dec). [α]D25 -258° (c = 0.5 in 0.1N H2SO4). Solubilities: Marsh, Weiss, J. Assoc. Off. Anal. Chem. 50, 457 (1967).Derivative
Hydrochloride.Nomenclature
CAS number: 64-73-3
Clortetrin (Fargal); Demetraciclina (Bios); Detravis (Vis); Meciclin (Citobios); Mexocine (Specia). Properties
LD50 orally in rats: 2372 mg/kg (Goldenthal).Therapeutic Category
Antibacterial.
Therapeutic Category (Veterinary)
Antibacterial.Keywords
Antibacterial (Antibiotics); Tetracyclines