4309. Furosemide

Nomenclature

CAS number: 54-31-9
5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid; 4-chloro-N-furfuryl-5-sulfamoylanthranilic acid; 4-chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic acid; frusemide; fursemide; LB-502; Aisemide; Beronald (Kowa); Desdemin (Vitacain); Discoid (Sagitta); Diural (Apothokermes); Dryptal (Berk); Durafurid (Durachemie); Errolon; Eutensin (Aventis); Frusetic (Unimed); Frusid (DDSA); Fulsix (Tatsumi); Fuluvamide (Mect); Furesis (BMS); Furo-Puren (Klinge-Nattermann); Furosedon (Santen); Hydro-rapid (Sanorania); Impugan (Dumex); Katlex (Iwaki); Lasilix (Aventis); Lasix (Aventis); Lowpston (Maruko); Macasirool (Hishiyama); Mirfat (Merckle); Nicorol (Lundbeck); Odemase (Azupharma); Oedemex (Mepha); Profemin (Yamanouchi); Rosemide (Ono); Rusyde (CP); Trofurit (Chinoin); Urex (Mochida).
C12H11ClN2O5S; mol wt 330.74.
C 43.58%, H 3.35%, Cl 10.72%, N 8.47%, O 24.19%, S 9.69%.

Description and references

Prepn: K. Stürm et al., DE 1122541; eidem, US 3058882 (both 1962 to Hoechst). Molecular and crystal structure: J. Lamotte et al., Acta Crystallogr. B34, 1657 (1978). Review of pharmacokinetics: L. Z. Benet, J. Pharmacokinet. Biopharm. 7, 1-27 (1979); R. E. Cutler, A. D. Blair, Clin. Pharmacokinet. 4, 279-296 (1979). Pharmacodynamics and pharmacokinetics of a slow-release formulation in man: A. Ebihara et al., Arzneim.-Forsch. 33, 163 (1983). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Comprehensive description: A. M. Al-Obaid et al., Anal. Profiles Drug Subs. 18, 153-193 (1989).

Chemical structure

Properties

Crystals from aq ethanol, mp 206°. uv max (95% ethanol): 288, 276, 336 nm (E1%1cm 945, 588, 144); (0.1N NaOH): 226, 273, 336 nm (E1%1cm 1147, 557, 133). Slightly sol in water, chloroform, ether. Sol in acetone, methanol, DMF, aq solns above pH 8.0. Less sol in ethanol. Pharmaceut. Incompat: Calcium gluconate, ascorbic acid, tetracyclines, urea, epinephrine. LD50 orally in female, male rats: 2600, 2820 mg/kg (Goldenthal).

Therapeutic Category

Diuretic; antihypertensive.

Therapeutic Category (Veterinary)

Diuretic.

Keywords

Antihypertensive; Sulfonamide Derivatives; Diuretic; Sulfonamide Derivatives