Substance
ID:449705
Names and Identifiers
IUPAC name
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Synonyms
TrimethoprimSyraprimTrimpex
IUPAC Traditional name
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Registration numbers
CAS Number
Properties
Pharmacology Properties
Mechanism of Action
Binding to bacterial enzyme is stronger than to the corresponding mammalian enzyme
Reversible dihydrofolate-reductase-inhibitor
Bacterial biosynthesis of nucleic acids and proteins is blocked by interference with normal bacterial metabolism of folinate
Blocks production of tetrahydrofolate from dihydrofolate
Folate antagonist
Product Information
Application(s)
Antiseptic
Active against common urinary-tract pathogens except for Pseudomonas aeruginosa
Antibacterial agent
Active against Haemophilus-influenzae.
Inhibits dihydrofolate reductase from bacterial sources and from malaria parasites
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• Koetzle, T.F. et al., J.A.C.S., 1976, 98, 2074, (cryst struct)
• Huovinen, P., Antimicrob. Agents Chemother., 1987, 31, 1451, (rev, props)
• Brossi, A. et al., J. Med. Chem., 1971, 14, 462, (synth)
• Bryan, R.F. et al., Acta Cryst. C, 1987, 43, 2412, (cryst struct)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 219
• Burchall, J.J., Antibiotics (N.Y.), 1975, 3, 304, (rev)
• Sigel, C.W., Handb. Exp. Pharmacol., 1983, 64, 163, (rev, metab)
• Roth, B. et al., J. Med. Chem., 1980, 23, 379; 535, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4092
• Manius, G.J., Anal. Profiles Drug Subst., 1978, 7, 445, (rev, synth, props, anal)
• Brogden, R.N. et al., Drugs, 1982, 23, 405, (rev, pharmacol)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TKX000; TKZ000