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Compound Detail

CHEMBL3317856

GEPOTIDACIN
🧪 Phase III
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🧪 Phase III
O=c1ccc2ncc(=O)n3c2n1C[C@H]3CN1CCC(NCc2cc3c(cn2)OCCC3)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3317856
Name GEPOTIDACIN
Phase Phase III
Structure Type MOL
InChI Key PZFAZQUREQIODZ-LJQANCHMSA-N

Known Names

Gepotidacin Gepotidacina Gepotidacine GSK-2140944 GSK2140944
5
Targets
21
Activities
1
Assay Types
1
PK Parameters
20
Publications
5
Known Names
5
Indications
2
Mechanisms

Molecular Properties

448.5
MW (Da)
1.09
ALogP
9
HBA
1
HBD
94.3
PSA (Ų)
0.62
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -dacin
USAN Year 2015

Extended Properties

Molecular Formula C24H28N6O3
MW 448.53
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -0.89

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Topoisomerase IV inhibitor INHIBITOR Topoisomerase IV ✓ ✓
Bacterial DNA gyrase inhibitor INHIBITOR Bacterial DNA gyrase ✓ ✓

Indications

Bacterial Infections Gonorrhea Urinary Tract Infections Infections Respiratory Tract Infections

ATC Classification

J01XX13
gepotidacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 21 meas. best 7.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 7.46 6.945 35.0 4
DNA gyrase
CHEMBL3038482
 IC50 7.33 6.8167 47.0 6
DNA gyrase
CHEMBL2094139
 IC50 7.22 6.915 60.0 2
Topoisomerase IV
CHEMBL3038508
 IC50 6.22 5.4825 600.0 4
DNA topoisomerase 2-alpha
CHEMBL1806
 IC50 4.26 4.26 55200.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 15606.54 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 35.0 nM 7.46 Inhibition of Escherichia coli topoisomerase 4 assessed as reduction in decatena... 35231579
DNA gyrase IC50 = 47.0 nM 7.33 Inhibition of Staphylococcus aureus DNA gyrase 31276392
DNA gyrase IC50 = 47.0 nM 7.33 Inhibition of Staphylococcus aureus DNA gyrase using positively supercoiled pBR3... 32027491
Unchecked IC50 = 49.0 nM 7.31 Inhibition of Escherichia coli topoisomerase 4 assessed as reduction in decatena... 34527181
Unchecked IC50 = 49.0 nM 7.31 Inhibition of Escherichia coli DNA topoisomerase 4 relaxation activity measured ... 36753879
DNA gyrase IC50 = 60.0 nM 7.22 Inhibition of Escherichia coli DNA gyrase supercoiling activity 35231579
DNA gyrase IC50 = 170.0 nM 6.77 Inhibition of Staphylococcus aureus Gyrase supercoiling activity assessed as red... 34614347
DNA gyrase IC50 = 244.0 nM 6.61 Inhibition of Escherichia coli DNA gyrase supercoiling incubated for 30 mins in ... 36753879
DNA gyrase IC50 = 244.0 nM 6.61 Inhibition of Escherichia coli DNA gyrase assessed as reduction in DNA supercoil... 34527181
DNA gyrase IC50 = 374.0 nM 6.43 Inhibition of Staphylococcus aureus DNA gyrase assessed as reduction in DNA supe... 34527181
DNA gyrase IC50 = 374.0 nM 6.43 Inhibition of Staphylococcus aureus DNA gyrase supercoiling incubated for 30 min... 36753879
Topoisomerase IV IC50 = 600.0 nM 6.22 Inhibition of Staphylococcus aureus DNA topoisomerase 4 31276392
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of Mycobacterium abscessus DNA gyrase using pBR322 DNA as substrate m... 35300094
Topoisomerase IV IC50 = 2800.0 nM 5.55 Inhibition of Staphylococcus aureus topoisomerase IV decatenation activity using... 34614347
Topoisomerase IV IC50 = 8299.0 nM 5.08 Inhibition of Staphylococcus aureus topoisomerase 4 assessed as reduction in dec... 34527181
Topoisomerase IV IC50 = 8299.0 nM 5.08 Inhibition of Staphylococcus aureus DNA topoisomerase 4 relaxation activity meas... 36753879
DNA topoisomerase 2-alpha IC50 = 55200.0 nM 4.26 Inhibition of human topoisomerase 2 assessed as reduction in decatenation 35231579

Literature References

PubMed DOI Target Context # Activities
37150058 10.1016/j.ejmech.2023.115413 Staphylococcus aureus 7
36753879 10.1016/j.ejmech.2023.115160 Staphylococcus aureus 7
32027491 10.1021/acs.jmedchem.9b01738 Streptococcus pneumoniae 5
34614347 10.1021/acs.jmedchem.1c01250 Staphylococcus aureus 5
35231579 10.1016/j.bmcl.2022.128648 Escherichia coli 5
36753879 10.1016/j.ejmech.2023.115160 Escherichia coli 4
34614347 10.1021/acs.jmedchem.1c01250 DNA gyrase 4
32027491 10.1021/acs.jmedchem.9b01738 Staphylococcus aureus 4
36753879 10.1016/j.ejmech.2023.115160 Unchecked 4
35300094 10.1021/acsmedchemlett.1c00549 Unchecked 4
39140037 10.1021/acsmedchemlett.4c00162 Staphylococcus aureus 3
32027491 10.1021/acs.jmedchem.9b01738 Escherichia coli 3
34527181 10.1021/acsmedchemlett.1c00345 Staphylococcus aureus 3
39140037 10.1021/acsmedchemlett.4c00162 Salmonella typhimurium 3
34527181 10.1021/acsmedchemlett.1c00345 Escherichia coli 3
35231579 10.1016/j.bmcl.2022.128648 ADMET 2
35231579 10.1016/j.bmcl.2022.128648 Acinetobacter baumannii 2
35231579 10.1016/j.bmcl.2022.128648 Pseudomonas aeruginosa 2
37506559 10.1016/j.bmc.2023.117381 ADMET 2
36753879 10.1016/j.ejmech.2023.115160 DNA gyrase 2

Data from ChEMBL 36 via Core Engine