Trimethoprim

• Catalog No.: Bio-0740
• CAS Number: 738-70-5
• M. F.: C14H18N4O3
• M. W.: 290.31772

SYNONYMS

• IUPAC name: 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• IUPAC Traditional name: 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• Synonyms: Trimpex; Syraprim

DATABASE IDS

• CAS Number: 738-70-5

PROPERTIES

• Application(s): Antibacterial agent
• Application(s): Antiseptic
• Application(s): Inhibits dihydrofolate reductase from bacterial sources and from malaria parasites
• Application(s): Active against common urinary-tract pathogens except for Pseudomonas aeruginosa
• Application(s): Active against Haemophilus-influenzae.
• Mechanism of Action: Folate antagonist
• Mechanism of Action: Bacterial biosynthesis of nucleic acids and proteins is blocked by interference with normal bacterial metabolism of folinate
• Mechanism of Action: Binding to bacterial enzyme is stronger than to the corresponding mammalian enzyme
• Mechanism of Action: Reversible dihydrofolate-reductase-inhibitor
• Mechanism of Action: Blocks production of tetrahydrofolate from dihydrofolate

REFERENCES

• Brossi, A. et al., J. Med. Chem., 1971, 14, 462, (synth)
• Burchall, J.J., Antibiotics (N.Y.), 1975, 3, 304, (rev)
• Koetzle, T.F. et al., J.A.C.S., 1976, 98, 2074, (cryst struct)
• Manius, G.J., Anal. Profiles Drug Subst., 1978, 7, 445, (rev, synth, props, anal)
• Sigel, C.W., Handb. Exp. Pharmacol., 1983, 64, 163, (rev, metab)
• Roth, B. et al., J. Med. Chem., 1980, 23, 379; 535, (synth)
• Brogden, R.N. et al., Drugs, 1982, 23, 405, (rev, pharmacol)
• Bryan, R.F. et al., Acta Cryst. C, 1987, 43, 2412, (cryst struct)
• Huovinen, P., Antimicrob. Agents Chemother., 1987, 31, 1451, (rev, props)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 219
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4092
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TKX000; TKZ000