3440. Doxycycline

Nomenclature

CAS number: 17086-28-1 (monohydrate); 564-25-0 (anhydrous)
[4S-(4α,4aα,5α,5aα,6α,12aα)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide monohydrate; α-6-deoxy-5-hydroxytetracycline monohydrate; α-6-deoxyoxytetracycline monohydrate; 5-hydroxy-α-6-deoxytetracycline monohydrate; GS-3065; Doxirobe (Pharmacia & Upjohn); Supracyclin (Grünenthal).
C22H24N2O8.H2O; mol wt 462.45.
C 57.14%, H 5.67%, N 6.06%, O 31.14%.

Description and references

Prepn of family of 6-deoxytetracyclines: C. R. Stephens et al., J. Am. Chem. Soc. 80, 5324 (1958). See also: McCormick, Jensen, US 3019260 (1962 to Am. Cyanamid). Prepn, separation and configuration of 6α- and 6β-epimers: M. S. von Wittenau et al., J. Am. Chem. Soc. 84, 2645 (1962); C. R. Stephens et al., ibid. 85, 2643 (1963). Prepn of 6α-deoxyoxytetracycline: R. K. Blackwood et al., US 3200149 (1965 to Pfizer). 1H-NMR study: M. S. von Wittenau, R. K. Blackwood, J. Org. Chem. 31, 613 (1966). Biological properties: English, Proc. Soc. Exp. Biol. Med. 122, 1107 (1966). Pharmacology: Fabre, Chemotherapia 11, 73 (1966); Gibaldi, ibid. 12, 265 (1967). Toxicity of hyclate: Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Clinical trial in prophylaxis of leptospirosis: E. T. Takafuji et al., N. Engl. J. Med. 310, 497 (1984). Clinical trial in periodontitis: A. M. Polson et al., J. Periodontol. 68, 110, 119 (1997). Review: C. Edwards in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 305-332.

Chemical structure

Derivative

Hydrochloride hemiethanolate hemihydrate.

Nomenclature

CAS number: 24390-14-5
Doxycycline hyclate; Atridox (Atrix); Azudoxat (Azupharma); Bassado (Pharmacia); Clinofug (Wolff); Diocimex (Cimex); Doryx (Faulding); Doxicrisol (Quimifar); Doxylar (Sandoz); Duradoxal (Merck KGaA); Granudoxy (Pierre Fabre); Mespafin (Merckle); Retens (Chiesi); Ronaxan (Merial); Spanor (Bailleul); Tetradox (Ranbaxy); Unacil (Firma); Vibramycin (Pfizer); Vibra-Tabs (Pfizer); Vibraveineuse (Pfizer); Vibraven"os (Pfizer); Zadorin (Mepha).
C22H25ClN2O8. 1/2 C2H6O. 1/2 H2O; mol wt 512.94.
C 53.86%, H 5.70%, Cl 6.91%, N 5.46%, O 28.07%.

Properties

Light yellow, crystalline powder from ethanol + HCl. Chars without melting at about 201°. [α]D25 -110° (c = 1 in 0.01N methanolic HCl). uv max (0.01N methanolic HCl): 267, 351 nm (log ε 4.24, 4.12). Sol in water. The alcohol and water of crystallization are lost by drying at 100° under reduced pressure. More active biologically than the corresponding 6β-epimer hydrochloride (Wittenau, 1962). LD50 i.p. in rats: 262 mg/kg (Goldenthal).

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); Tetracyclines