2309. Cinoxacin

Nomenclature

CAS number: 28657-80-9
1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid; 1-ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid; compd 64716; Cinobac (Lilly); Noxigram (Firma); Uronorm (Alfa).
C12H10N2O5; mol wt 262.22.
C 54.96%, H 3.84%, N 10.68%, O 30.51%.

Description and references

Quinolone antibacterial; analog of oxolinic acid, q.v. Prepn: W. A. White, DE 2005104; idem, US 3669965 (1970, 1972 both to Lilly). In vitro and in vivo study: W. E. Wick et al., Antimicrob. Agents Chemother. 4, 415 (1973). Pharmacology: J. J. Szwed et al., J. Antimicrob. Chemother. 4, 451 (1978); K. S. Israel et al., J. Clin. Pharmacol. 18, 491 (1978). Metabolism: R. L. Wolen et al. in Stable Isotopes, T. A. Baillie, Ed. (Univ. Park Press, Baltimore, 1978) pp 113-125. Clinical studies: S. Colleen et al., J. Antimicrob. Chemother. 3, 579 (1977); S. N. Rous, J. Urol. 120, 196 (1978). Toxicity: I. Narama et al., Chemotherapy (Tokyo) 28, Suppl. 4, 406 (1980), C.A. 94, 25007 (1981). Pharmacokinetics: M. Ohkawa et al., J. Antimicrob. Chemother. 8, 447 (1981); R. Barbhaiya et al., Antimicrob. Agents Chemother. 21, 472 (1982). Review: J. M. Scavone et al., Pharmacotherapy 2, 266-271 (1982). Review of pharmacology and therapeutic efficacy: T. S. Sisca et al., Drugs 25, 544-569 (1983).

Chemical structure

Properties

Light tan crystals, mp 261-262° (dec). Sol in most polar organic solvents. LD50 in rats (mg/kg): 4160 orally; 900 i.v. (Narama).

Derivative

Sodium salt.
C12H9N2NaO5; mol wt 284.20.
C 50.71%, H 3.19%, N 9.86%, Na 8.09%, O 28.15%.

Properties

White crystalline solid. Sol in aqueous solvents.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Quinolones and Analogs