1380. Brodimoprim

Nomenclature

CAS number: 56518-41-3
5-[(4-Bromo-3,5-dimethoxyphenyl)methyl]-2,4-pyrimidinediamine; 2,4-diamino-5-(4-bromo-3,5-dimethoxybenzyl)pyrimidine; Ro-10-5970.
C13H15BrN4O2; mol wt 339.19.
C 46.03%, H 4.46%, Br 23.56%, N 16.52%, O 9.43%.

Description and references

Dihydrofolate reductase inhibitor; structural analog of trimethoprim, q.v. Prepn: M. Hoffer, I. Kompis, DE 2452889 (1975 to Hoffmann-La Roche), C.A. 83, 97361 (1975); I. Kompis, US 4024145 (1977 to Hoffmann-La Roche); I. Kompis, A. Wick, Helv. Chim. Acta 60, 3025 (1977). Antibacterial activity: G. Giammanco et al., Drugs Exp. Clin. Res. 9, 721 (1983). Comparison with trimethoprim as inhibitor of dihydrofolate reductase: R. L. Then et al., Rev. Infect. Dis. 4, 372 (1982); R. L. Then, F. Hermann, Chemotherapy (Basel) 30, 18 (1984). Antimycobacterial activity in vitro: J. K. Seydel et al., ibid. 29, 249 (1983). Pharmacokinetics in human serum, skin blister fluid: T. Kalager et al., Chemotherapy (Basel) 31, 405 (1985). Clinical evaluation in respiratory infections: H. A. Salmi et al., Drugs Exp. Clin. Res. 12, 349 (1986); in urinary tract infections: F. Scaglione et al., Int. J. Clin. Pharmacol. Res. 15, 121 (1995); in bacterial cystitis: E. V. Cosmi et al., Eur. J. Obstet. Gynecol. Reprod. Biol. 64, 207 (1996).

Chemical structure

Properties

Crystals from methanol, mp 225-228°. pKa 7.15.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); 2,4-Diaminopyrimidines