Title: Bumetanide
CAS Registry Number: 28395-03-1
CAS Name: 3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid
Additional Names: 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
Manufacturers' Codes: PF-1593; Ro-10-6338
Trademarks: Bumex (Roche); Burinex (Leo Pharm); Butinat (Gramon); Fontego (Polifarma); Fordiuran (Thomae); Lunetoron (Sankyo)
Molecular Formula: C17H20N2O5S
Molecular Weight: 364.42
Percent Composition: C 56.03%, H 5.53%, N 7.69%, O 21.95%, S 8.80%
Literature References: Prepn: P. W. Feit, DE 1964503 and DE 1964504; idem, US 3806534 (1970, 1970, 1974 all to Lövens Kemiske Fabrik); idem, J. Med. Chem. 14, 432 (1971). Pharmacology: E. H. Oestergaard et al., Arzneim.-Forsch. 22, 66 (1972). HPLC and GC/MS determn in urine: C. Y. Gradeen et al., J. Anal. Toxicol. 14, 123 (1990). Review of pharmacology and therapeutic use: A. Ward, R. C. Heel, Drugs 28, 426-464 (1984). Series of articles on pharmacokinetics and comparative clinical studies in combination therapy: Curr. Ther. Res. 50, Suppl. A, 1-82 (1991). Comprehensive description: P. N. V. Tata et al., Anal. Profiles Drug Subs. Excip. 22, 107-144 (1993).
Properties: Crystals from aq ethanol, mp 230-231°. pK1 3.6, pK2 7.7. Soly (mg/ml): water 0.1; ethanol 30.6; propylene glycol 18.7; dimethylacetamide >500; methanol 76.5; benzene 0.4; benzyl alcohol 21.6; acetone 50.2. Sol in alkaline solns. uv max (water): 260, 220 nm (E1% 18.9, 17.1); (0.1 N NaOH): 326 nm; (methanol): 270, 345 nm. LD50 i.v. in mice: 330 mg/kg (Oestergaard).
Melting point: mp 230-231°
pKa: pK1 3.6, pK2 7.7
Absorption maximum: uv max (water): 260, 220 nm (E1% 18.9, 17.1)
Toxicity data: LD50 i.v. in mice: 330 mg/kg (Oestergaard)
Therap-Cat: Diuretic.
Keywords: Diuretic; Sulfonamide Derivatives. |