ICLAPRIM

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
ATC J01EA03
UNII 42445HUU0O

Structure

InChI Key HWJPWWYTGBZDEG-UHFFFAOYSA-N
Smiles COc1cc(Cc2cnc(N)nc2N)c2c(c1OC)OC(C1CC1)C=C2
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H22N4O3
Molecular Weight 354.41
AlogP 2.43
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 105.51
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 26.0

Bioactivity

Mechanism of Action Action Reference
Bacterial dihydrofolate reductase inhibitor INHIBITOR PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 2-27 - 0-1 -
Assay Description Organism Bioactivity Reference
Inhibition of Staphylococcus aureus dihydrofolate reductase (DHFR) enzyme by trimethoprim (TMP) Staphylococcus aureus 7.0 nM
Inhibition of Streptococcus pneumoniae dihydrofolate reductase (DHFR) enzyme by trimethoprim (TMP) Streptococcus pneumoniae 8.0 nM
Inhibition of Escherichia coli dihydrofolate reductase (DHFR) enzyme by trimethoprim (TMP) Escherichia coli 7.0 nM
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at <= 0.008 ug/ml by CLSI broth microdilution method Staphylococcus aureus 0.1 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 0.015 ug/ml by CLSI broth microdilution method Staphylococcus aureus 0.3 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 0.03 ug/ml by CLSI broth microdilution method Staphylococcus aureus 6.1 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 0.06 ug/ml by CLSI broth microdilution method Staphylococcus aureus 58.8 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 0.12 ug/ml by CLSI broth microdilution method Staphylococcus aureus 95.6 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 0.25 ug/ml by CLSI broth microdilution method Staphylococcus aureus 98.5 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 0.5 ug/ml by CLSI broth microdilution method Staphylococcus aureus 98.6 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 1 ug/ml by CLSI broth microdilution method Staphylococcus aureus 98.7 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 2 ug/ml by CLSI broth microdilution method Staphylococcus aureus 98.7 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 4 ug/ml by CLSI broth microdilution method Staphylococcus aureus 99.9 %
Antibacterial activity against Methicillin-sensitive Staphylococcus aureus assessed as inhibition of bacterial growth at 8 ug/ml by CLSI broth microdilution method Staphylococcus aureus 100.0 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at <= 0.008 ug/ml by CLSI broth microdilution method Staphylococcus aureus 0.1 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 0.015 ug/ml by CLSI broth microdilution method Staphylococcus aureus 0.4 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 0.03 ug/ml by CLSI broth microdilution method Staphylococcus aureus 12.8 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 0.06 ug/ml by CLSI broth microdilution method Staphylococcus aureus 69.6 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 0.12 ug/ml by CLSI broth microdilution method Staphylococcus aureus 91.1 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 0.25 ug/ml by CLSI broth microdilution method Staphylococcus aureus 92.3 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 0.5 ug/ml by CLSI broth microdilution method Staphylococcus aureus 92.9 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 1 ug/ml by CLSI broth microdilution method Staphylococcus aureus 93.8 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 2 ug/ml by CLSI broth microdilution method Staphylococcus aureus 94.6 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 4 ug/ml by CLSI broth microdilution method Staphylococcus aureus 97.9 %
Antibacterial activity against Methicillin-resistant Staphylococcus aureus assessed as inhibition of bacterial growth at 8 ug/ml by CLSI broth microdilution method Staphylococcus aureus 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at <= 0.008 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 30.5 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 0.015 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 77.6 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 0.03 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 94.9 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 0.06 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 99.3 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 0.12 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 0.25 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 0.5 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 1 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 2 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 4 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group A assessed as inhibition of bacterial growth at 8 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group A' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at <= 0.008 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 0.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 0.015 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 0.5 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 0.03 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 0.5 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 0.06 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 5.4 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 0.12 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 55.4 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 0.25 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 91.2 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 0.5 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 1 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 2 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 4 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 100.0 %
Antibacterial activity against Beta-hemolytic Streptococcus group B assessed as inhibition of bacterial growth at 8 ug/ml by CLSI broth microdilution method Streptococcus sp. 'group B' 100.0 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at <= 0.008 ug/ml by CLSI broth microdilution method Enterococcus faecalis 29.0 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 0.015 ug/ml by CLSI broth microdilution method Enterococcus faecalis 57.7 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 0.03 ug/ml by CLSI broth microdilution method Enterococcus faecalis 63.9 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 0.06 ug/ml by CLSI broth microdilution method Enterococcus faecalis 67.1 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 0.12 ug/ml by CLSI broth microdilution method Enterococcus faecalis 69.0 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 0.25 ug/ml by CLSI broth microdilution method Enterococcus faecalis 70.6 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 0.5 ug/ml by CLSI broth microdilution method Enterococcus faecalis 70.6 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 1 ug/ml by CLSI broth microdilution method Enterococcus faecalis 71.0 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 2 ug/ml by CLSI broth microdilution method Enterococcus faecalis 71.9 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 4 ug/ml by CLSI broth microdilution method Enterococcus faecalis 96.8 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at 8 ug/ml by CLSI broth microdilution method Enterococcus faecalis 1.9 %
Antibacterial activity against Enterococcus faecalis assessed as inhibition of bacterial growth at >8 ug/ml by CLSI broth microdilution method Enterococcus faecalis 100.0 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at <= 0.008 ug/ml by CLSI broth microdilution method Enterococcus faecium 33.7 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 0.015 ug/ml by CLSI broth microdilution method Enterococcus faecium 36.3 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 0.03 ug/ml by CLSI broth microdilution method Enterococcus faecium 37.6 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 0.06 ug/ml by CLSI broth microdilution method Enterococcus faecium 37.6 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 0.12 ug/ml by CLSI broth microdilution method Enterococcus faecium 38.0 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 0.25 ug/ml by CLSI broth microdilution method Enterococcus faecium 38.3 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 0.5 ug/ml by CLSI broth microdilution method Enterococcus faecium 39.3 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 1 ug/ml by CLSI broth microdilution method Enterococcus faecium 42.2 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 2 ug/ml by CLSI broth microdilution method Enterococcus faecium 58.1 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 4 ug/ml by CLSI broth microdilution method Enterococcus faecium 74.9 %
Antibacterial activity against Enterococcus faecium assessed as inhibition of bacterial growth at 8 ug/ml by CLSI broth microdilution method Enterococcus faecium 75.6 %
Inhibition of Staphylococcus aureus wild type recombinant DHFR by MTS assay Staphylococcus aureus 2.2 nM Inhibition of Staphylococcus aureus wild type recombinant DHFR by MTS assay Staphylococcus aureus 2.6 nM
Inhibition of Staphylococcus aureus DHFR F98Y mutant by MTS assay Staphylococcus aureus 27.0 nM
Inhibition of Staphylococcus aureus DHFR assessed as oxidation of NADPH using dihydrofolate as substrate pre-incubated for 10 mins before substrate addition by spectrophotometry Staphylococcus aureus 0.081 nM
Inhibition of Haemophilus influenzae DHFR assessed as oxidation of NADPH using dihydrofolate as substrate pre-incubated for 10 mins before substrate addition by spectrophotometry Haemophilus influenzae 0.007 nM
Inhibition of human DHFR assessed as oxidation of NADPH using dihydrofolate as substrate pre-incubated for 10 mins before substrate addition by spectrophotometry Homo sapiens 775.0 nM
Inhibition of TMP-resistant Staphylococcus aureus DHFR F99Y mutant assessed as oxidation of NADPH using dihydrofolate as substrate pre-incubated for 10 mins before substrate addition by spectrophotometry Staphylococcus aureus 0.9 nM
Inhibition of human DHFR using dihydrofolate as substrate preincubated for 10 mins followed by substrate addition by spectrophotometric analysis in presence of NADPH Homo sapiens 775.0 nM
Inhibition of Staphylococcus aureus DHFR using dihydrofolate as substrate preincubated for 10 mins followed by substrate addition by spectrophotometric analysis in presence of NADPH Staphylococcus aureus 0.08 nM

Cross References

Resources Reference
ChEBI 131751
ChEMBL CHEMBL134561
DrugBank DB06358
DrugCentral 4573
FDA SRS 42445HUU0O
Guide to Pharmacology 10820
PubChem 213043
SureChEMBL SCHEMBL379386
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