6655. Nitroxoline

Nomenclature

CAS number: 4008-48-4
5-Nitro-8-quinolinol; 5-nitro-8-hydroxyquinoline; Enterocol; Nibiol; Noxibiol; Uritrol; Urocoli.
C9H6N2O3; mol wt 190.16.
C 56.84%, H 3.18%, N 14.73%, O 25.24%.

Description and references

Prepn: Kostanecki, Ber. 24, 154 (1891); Petrow, Sturgeon, J. Chem. Soc. 1954, 570; Pratt, Duke, J. Am. Chem. Soc. 82, 1155 (1960). In vitro antibacterial and antifungal activity: A. Desvignes, P. Leguen, Ann. Pharm. Fr. 21, 803 (1963); M. Medic-Saric et al., Chemotherapy 26, 263 (1980). Toxicological study: O. Angelova et al., Adv. Antimicrob. Antineoplast. Chemother., Proc. 7th Int. Congr. Chemother. 1, 507 (1972). Clinical pharmacokinetics: A. Mrhar et al., Int. J. Clin. Pharmacol. Biopharm. 17, 476 (1979). HPLC determn in plasma and urine: R. H. A. Sorel et al., J. Chromatogr. 222, 241 (1981). Clinical evaluation in urinary tract infections: M. R. Jacobs et al., S. Afr. Med. J. 54, 959 (1978); B. Cancet, A. Amgar, Pathol. Biol. 35, 879 (1987).

Chemical structure

Properties

Yellow needles from alcohol or acetic acid, mp 179.5-181.5°. Freely sol in alkali and hot HCl; sparingly sol in alcohol, ether.

Derivative

Hydrochloride.
C9H7ClN2O3; mol wt 226.62.
C 47.70%, H 3.11%, Cl 15.64%, N 12.36%, O 21.18%.

Properties

Yellow needles from alcohol, mp 258°.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic)