6202. Minocycline

Nomenclature

CAS number: 10118-90-8
[4S-(4α,4aα,5aα,12aα)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide; 7-dimethylamino-6-demethyl-6-deoxytetracycline.
C23H27N3O7; mol wt 457.48.
C 60.38%, H 5.95%, N 9.19%, O 24.48%.

Description and references

Second generation tetracycline antibiotic. Prepn: J. Petisi, J. H. Boothe, US 3226436 (1965 to Am. Cyanamid); M. J. Martell, J. H. Boothe, J. Med. Chem. 10, 44 (1967); R. F. R. Church et al., J. Org. Chem. 36, 723 (1971). HPLC determn in tissue and serum: W. R. Wrightson et al., J. Chromatogr. B 706, 358 (1998). Comprehensive description: V. Zbinovsky, G. P. Chrekian, Anal. Profiles Drug Subs. 6, 323-339 (1977). Series of articles on toxicology and metabolism: Toxicol. Appl. Pharmacol. 11, 128-183 (1967). Review of antibacterial activity and pharmacology: M. Jonas, B. A. Cunha, Ther. Drug Monit. 4, 137-145 (1982); of clinical safety and efficacy in acne: K. Freeman, Br. J. Clin. Pract. 43, 112-115 (1989). Clinical evaluation in periodontal disease: R. J. Oringer et al., J. Periodontol. 73, 835 (2002); in Huntington disease: Huntington Study Group, Neurology 63, 547 (2004). Review of clinical potential in neurodegenerative disorders: D. Blum et al., Neurobiol. Dis. 17, 359-366 (2004); in acute neurologic injury: H. F. Elewa et al., Pharmacotherapy 26, 515-521 (2006).

Chemical structure

Properties

Bright yellow-orange amorphous solid. [α]D25 -166° (c = 0.524). uv max (0.1N HCl): 352, 263 nm (log ε 4.16, 4.23); (0.1N NaOH): 380, 243 nm (log ε 4.30, 4.38).

Derivative

Hydrochloride.

Nomenclature

CAS number: 13614-98-7
Arestin (OroPharma); Dynacin (Medicis); Klinomycin (Valeant); Minocin (Wyeth); Vectrin (Medicis).
C23H27N3O7.HCl; mol wt 493.94.
C 55.93%, H 5.71%, N 8.51%, O 22.67%, Cl 7.18%.

Properties

Yellow crystalline powder. Slightly hygroscopic; sensitive to light and to surface oxidation.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); Tetracyclines