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Compound Detail

CHEMBL134561

ICLAPRIM
🧪 Phase III
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🧪 Phase III
COc1cc(Cc2cnc(N)nc2N)c2c(c1OC)OC(C1CC1)C=C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL134561
Name ICLAPRIM
Phase Phase III
Structure Type MOL
InChI Key HWJPWWYTGBZDEG-UHFFFAOYSA-N

Known Names

AR-100 Iclaprim Iclaprime RO 48-2622 RO-48-2622 Ro-482622
4
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
6
Known Names
4
Indications
1
Mechanisms

Molecular Properties

354.4
MW (Da)
2.43
ALogP
7
HBA
2
HBD
105.5
PSA (Ų)
0.85
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Racemic

Flags

Natural Product
USAN Stem -prim
USAN Year 2008

Extended Properties

Molecular Formula C19H22N4O3
MW 354.41
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 1.08

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial dihydrofolate reductase inhibitor INHIBITOR Dihydrofolate reductase ✓ ✓

Indications

Bacterial Infections Infections Skin Diseases Pneumonia, Ventilator-Associated

ATC Classification

J01EA03
iclaprim
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 8 meas. best 8.66
Ki 6 meas. best 10.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL1681620
 Ki 10.1 9.7467 0.1 3
Dihydrofolate reductase
CHEMBL1681620
 IC50 8.66 8.2425 2.2 4
Dihydrofolate reductase
CHEMBL1809
 IC50 8.15 7.665 7.0 2
Dihydrofolate reductase
CHEMBL202
 IC50 8.1 8.1 8.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 6.11 6.11 775.0 2
Dihydrofolate reductase
CHEMBL1926
 IC50 5.62 5.62 2400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 0.08 nM 10.1 Inhibition of Staphylococcus aureus DHFR using dihydrofolate as substrate preinc... 24428639
Dihydrofolate reductase Ki = 0.081 nM 10.09 Inhibition of Staphylococcus aureus DHFR assessed as oxidation of NADPH using di... 21831637
Dihydrofolate reductase Ki = 0.9 nM 9.05 Inhibition of TMP-resistant Staphylococcus aureus DHFR F99Y mutant assessed as o... 21831637
Dihydrofolate reductase IC50 = 2.2 nM 8.66 Inhibition of Staphylococcus aureus wild type recombinant DHFR by MTS assay 20606069
Dihydrofolate reductase IC50 = 2.6 nM 8.59 Inhibition of Staphylococcus aureus wild type recombinant DHFR by MTS assay 20606069
Dihydrofolate reductase IC50 = 7.0 nM 8.15 Inhibition of Escherichia coli dihydrofolate reductase (DHFR) enzyme by trimetho... 14623005
Dihydrofolate reductase IC50 = 7.0 nM 8.15 Inhibition of Staphylococcus aureus dihydrofolate reductase (DHFR) enzyme by tri... 14623005
Dihydrofolate reductase IC50 = 8.0 nM 8.1 Inhibition of Streptococcus pneumoniae dihydrofolate reductase (DHFR) enzyme by ... 14623005
Dihydrofolate reductase IC50 = 27.0 nM 7.57 Inhibition of Staphylococcus aureus DHFR F98Y mutant by MTS assay 20606069
Dihydrofolate reductase IC50 = 65.35 nM 7.18 Inhibition of Escherichia coli DHFR incubated for 10 mins in presence of NADPH b... 37698518
Dihydrofolate reductase Ki = 775.0 nM 6.11 Inhibition of human DHFR assessed as oxidation of NADPH using dihydrofolate as s... 21831637
Dihydrofolate reductase Ki = 775.0 nM 6.11 Inhibition of human DHFR using dihydrofolate as substrate preincubated for 10 mi... 24428639
Dihydrofolate reductase IC50 = 2400.0 nM 5.62 Inhibition of Pneumocystis carinii dihydrofolate reductase (DHFR) enzyme by trim... 14623005

Literature References

PubMed DOI Target Context # Activities
19289528 10.1128/aac.00129-09 Staphylococcus aureus 32
19139284 10.1128/aac.01388-08 Streptococcus pneumoniae 30
19564362 10.1128/aac.00325-09 Staphylococcus aureus 29
19651909 10.1128/aac.00766-09 Staphylococcus aureus 23
19289528 10.1128/aac.00129-09 Enterococcus faecalis 17
19289528 10.1128/aac.00129-09 Streptococcus sp. 'group A' 16
19289528 10.1128/aac.00129-09 Enterococcus faecium 16
19289528 10.1128/aac.00129-09 Streptococcus sp. 'group B' 16
24428639 10.1021/jm401204g Streptococcus pneumoniae 12
19139284 10.1128/aac.01388-08 ADMET 6
14623005 10.1016/j.bmcl.2003.07.023 Dihydrofolate reductase 5
20606069 10.1128/aac.00361-10 Dihydrofolate reductase 3
21831637 10.1016/j.bmcl.2011.07.059 Dihydrofolate reductase 3
21831637 10.1016/j.bmcl.2011.07.059 Staphylococcus aureus 3
14623005 10.1016/j.bmcl.2003.07.023 Mus musculus 3
24428639 10.1021/jm401204g Staphylococcus aureus 3
14623005 10.1016/j.bmcl.2003.07.023 Staphylococcus aureus 3
21831637 10.1016/j.bmcl.2011.07.059 Unchecked 2
24428639 10.1021/jm401204g Dihydrofolate reductase 2
19564362 10.1128/aac.00325-09 Serum 2

Data from ChEMBL 36 via Core Engine