Compound ID | 1965

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Trimethoprim

Class: Small molecule antibacterial agent

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Folate synthesis inhibitor. Dihydrofolate reductase inhibitor; DHFR inhibitor
Target Pathogen: Active against many Gram-positive, Gram-negative strains, and protozoal pathogens
Description: Synthetic compound; mostly used in fixed combination with sulfamethoxazole (synergistic combination) for treatment and prophylaxis; oral and parenteral application.; a diaminopyrimidine
Year first mentioned: 1962
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
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Molecular weight: 290.32
Iso. SMILES: COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
InChI Key: IEDVJHCEMCRBQM-UHFFFAOYSA-N
Can. SMILES: COC1=CC(=CC(=C1OC)OC)CC2=C(N)N=C(N)N=C2
InChI: InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5578
Guide to Pharmacology: trimethoprim
Citations:
  • https://academic.oup.com/jac/article-abstract/5/Supplement_B/27/724655?redirectedFrom=fulltext
  • https://pubmed.ncbi.nlm.nih.gov/8195838/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1147852/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC473737/

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