Brodimoprim

Title: Brodimoprim
CAS Registry Number: 56518-41-3
CAS Name: 5-[(4-Bromo-3,5-dimethoxyphenyl)methyl]-2,4-pyrimidinediamine
Additional Names: 2,4-diamino-5-(4-bromo-3,5-dimethoxybenzyl)pyrimidine
Manufacturers' Codes: Ro-10-5970
Molecular Formula: C13H15BrN4O2
Molecular Weight: 339.19
Percent Composition: C 46.03%, H 4.46%, Br 23.56%, N 16.52%, O 9.43%
Literature 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).
Properties: Crystals from methanol, mp 225-228°. pKa 7.15.
Melting point: mp 225-228°
pKa: pKa 7.15
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); 2,4-Diaminopyrimidines.
Bromacil Bromadiolone Bromal Bromal Hydrate Bromazepam

Brodimoprim
Brodimoprim.svg
Systematic (IUPAC) name
5-[(4-Bromo-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Clinical data
Legal status  ?
Identifiers
CAS number 56518-41-3 YesY
ATC code J01EA02
PubChem CID 68760
ChemSpider 62004 YesY
UNII V1YC7T6LLI YesY
KEGG D07238 YesY
ChEMBL CHEMBL31891 YesY
Chemical data
Formula C13H15BrN4O2 
Mol. mass 339.188 g/mol
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Brodimoprim is a structural derivative of trimethoprim. In brodimoprim, the 4-methoxy group of trimethoprim is replaced with a bromine atom.

As trimethoprim, brodimoprim is a selective inhibitor of bacterial dihydrofolate reductase.[1]