6157. Metronidazole

Nomenclature

CAS number: 443-48-1
2-Methyl-5-nitroimidazole-1-ethanol; 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole; 1-(β-ethylol)-2-methyl-5-nitro-3-azapyrrole; Bayer 5630; RP-8823; Acea Gel (Ferndale); Anabact (Cambridge Healthcare); Arilin (Wolff); Clont (Infectopharm); Deflamon (SPA); Elyzol (Dumex); Flagyl (Searle); Fossyol (Merckle); Klion (Gedeon Richter); MetroGel (Galderma); Metrolag (Lagap); Metrolyl (Sandoz); Metrosa (Linderma); Metrotop (Medlock); Orvagil (Galenika); Rathimed (Pfleger); Rosaced (Fabre); Rozacrème (Biorga); Rozagel (Biorga); Rozex (Galderma); Trichocide (Mitsubishi); Vagilen (Alfa); Vagimid (Apogepha); Zadstat (Wyeth); Zidoval (3M Pharma).
C6H9N3O3; mol wt 171.15.
C 42.11%, H 5.30%, N 24.55%, O 28.04%.

Description and references

Prepn: Jacob et al., US 2944061 (1960 to Rhne-Poulenc); Cossar et al., Arzneim.-Forsch. 16, 23 (1966). Activity studies: Bock, ibid. 11, 587 (1961). Metabolism: Ings et al., Biochem. Pharmacol. 15, 515 (1966). Comprehensive description: L. L. Wearley, G. D. Anthony, Anal. Profiles Drug Subs. 5, 327-344 (1976). Review of activity, pharmacokinetics and use in anaerobic infection: R. N. Brogden et al., Drugs 16, 387-417 (1978); in rosacea: L. K. Schmadel, G. K. McEvoy, Clin. Pharm. 9, 94-101 (1990). Review: W. D. Hager, R. P. Rapp, Obstet. Gynecol. Clin. North Am. 19, 497-510 (1992).

Chemical structure

Properties

Cream-colored crystals, mp 158-160°. Soly at 20° (g/100 ml): water 1.0; ethanol 0.5; ether <0.05; chloroform <0.05. Sparingly sol in DMF. Sol in dil acids. pH of satd aq soln: 5.8.

Derivative

Hydrochloride.

Nomenclature

CAS number: 69198-10-3
SC-326421.
C6H9N3O3.HCl; mol wt 207.61.
C 34.71%, H 4.85%, N 20.24%, O 23.12%, Cl 17.08%.

Caution

Metronidazole is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-173.

Therapeutic Category

Antiprotozoal (Trichomonas); antibacterial; in treatment of rosacea.

Therapeutic Category (Veterinary)

Antiprotozoal (Trichomonas); antiamebic; antibacterial.

Keywords

Antibacterial (Synthetic); Antiprotozoal (Trichomonas)