Compound ID | 1966

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Iclaprim

Synonym(s): AR-100  |  MTF-100  |  RO-48-2622

Class: Diaminopyrimidine

Spectrum of activity: Gram-positive
Details of activity: Inhibits dihydrofolic acid reductase and thus, the synthesis of purine. Active against Gram-positive bacteria including trimethoprim-resistant strains.
Description: Synthetic compound. Trimethoprim derivative
Institute where first reported: Roche, Arpida, Acino Pharma, Life Sciences Management Group, Nuprim, Motif BioSciences
Year first mentioned: 2003
Development status: Inactive
Reason Dropped: Rejected by the FDA due to failure to show non-inferiority and due to safety concerns
Chemical structure(s):
Click here for structure editor
Molecular weight: 354.4
Iso. SMILES: COC1=C(C2=C(C=CC(O2)C3CC3)C(=C1)CC4=CN=C(N=C4N)N)OC
InChI Key: HWJPWWYTGBZDEG-UHFFFAOYSA-N
Can. SMILES: COC1=C(C2=C(C=CC(C3CC3)O2)C(=C1)CC4=C(N)N=C(N)N=C4)OC
InChI: InChI=1S/C19H22N4O3/c1-24-15-8-11(7-12-9-22-19(21)23-18(12)20)13-5-6-14(10-3-4-10)26-16(13)17(15)25-2/h5-6,8-10,14H,3-4,7H2,1-2H3,(H4,20,21,22,23)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/213043
Guide to Pharmacology: iclaprim
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/31050628/
  • https://pubmed.ncbi.nlm.nih.gov/32081524/

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