13-08429. Sancycline [Archived]

Nomenclature

CAS number: 808-26-4
[4S-(4α,4aα,5aα,12aα)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide; 6-demethyl-6-deoxytetracycline; norcycline; Bonomycin (Pfizer).
C21H22N2O7; mol wt 414.41.
C 60.86%, H 5.35%, N 6.76%, O 27.03%.

Description and references

Semi-synthetic antibiotic related to tetracycline. Prepn: Beereboom et al., J. Am. Chem. Soc. 82, 1003 (1960); McCormick et al., ibid. 3381; McCormick, Jensen, US 3019260 (1962 to Am. Cyanamid); GB 901209 (1962 to Pfizer). Total synthesis: Conover et al., J. Am. Chem. Soc. 84, 3222 (1962).

Chemical structure

Derivative

Hydrochloride hemihydrate.
C21H22N2O7.HCl.H2O; mol wt 459.88.
C 54.85%, H 5.26%, N 6.09%, O 26.09%, Cl 7.71%.

Properties

Crystals from ethanol, dec 215-220°. uv max (MeOH/0.01N HCl): 267, 347 nm (ε 19300, 15500); in 0.1N H2SO4: 217, 268, 343 nm (ε 13400, 19000, 14600).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); Tetracyclines

Status

This monograph has been retired and is no longer subject to revision or update.