epiroprim   Click here for help

GtoPdb Ligand ID: 12327

Synonyms: Ro 11-8958 | TCMDC-137295
Compound class: Synthetic organic
Comment: Epiroprim belongs to the diaminopyrimidine class of antimicrobial compounds and is a structural analogue of trimethoprim [3]. It inhibits bacterial dihydrofolate reductase (DHFR) and has antibacterial and antiparasitic activities [2-3].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 100.69
Molecular weight 353.19
XLogP 2.65
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCOc1cc(cc(c1n1cccc1)OCC)Cc1cnc(nc1N)N
Isomeric SMILES CCOc1cc(cc(c1n1cccc1)OCC)Cc1cnc(nc1N)N
InChI InChI=1S/C19H23N5O2/c1-3-25-15-10-13(9-14-12-22-19(21)23-18(14)20)11-16(26-4-2)17(15)24-7-5-6-8-24/h5-8,10-12H,3-4,9H2,1-2H3,(H4,20,21,22,23)
InChI Key NMARPFMJVCXSAV-UHFFFAOYSA-N
Bioactivity Comments
Epiroprim is a potent selective inhibitor of bacterial DHFR, with an IC50 of 0.0025 μM for Escherichia coli and 0.0026 μM for Staphylococcus aureus [3]. MIC for antibacterial activity against E.coli is 0.04 μg/ml and 0.1 μg/ml against S. aureus in vitro [3].
The compound is effective against Toxoplasma gondii and Pneumocystis carinii in animal models and when used in combination with dapsone, provides a complete cure of toxoplasmosis in mice [2]. The same drug combination has been shown to be effective against a broad range of bacteria, including strains resistant to trimethoprim [1].