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Compound Detail

CHEMBL430

GEMIFLOXACIN
💊 Approved Drug
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💊 Approved Drug
CO/N=C1\CN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CC1CN
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL430
Name GEMIFLOXACIN
Phase Approved
Structure Type MOL
InChI Key ZRCVYEYHRGVLOC-HYARGMPZSA-N
Therapeutic ✓ Yes

Known Names

Factiv Gemifloxacin Gemifloxacine Gemifloxacino
5
Targets
13
Activities
1
Assay Types
26
PK Parameters
20
Publications
4
Known Names
5
Indications

Molecular Properties

389.4
MW (Da)
0.97
ALogP
8
HBA
2
HBD
123.0
PSA (Ų)
0.73
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2003
Availability Discontinued
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -oxacin
USAN Year 1998

Extended Properties

Molecular Formula C18H20FN5O4
MW 389.39
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.47

Indications

Bacterial Infections Helicobacter Infections Peritonitis Hypoglycemia Rhinoscleroma

ATC Classification

J01MA15
gemifloxacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 13 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DNA topoisomerase 4 subunit A
CHEMBL4088
 IC50 6.52 6.52 300.0 1
Unchecked
CHEMBL612545
 IC50 6.52 5.9567 300.0 6
DNA gyrase
CHEMBL2094139
 IC50 6.3 6.3 500.0 1
Dipeptidyl peptidase 4
CHEMBL284
 IC50 5.57 5.57 2700.0 1
DNA gyrase
CHEMBL3038482
 IC50 5.25 5.25 5600.0 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 8500.0 ng.hr.mL-1 Rattus norvegicus
AUC 7550.0 ng.hr.mL-1 Canis lupus familiaris
AUC 25790.0 ng.hr.mL-1 Rattus norvegicus
AUC 9000.0 ng.hr.mL-1 Homo sapiens
Cmax 6266.21 nM Rattus norvegicus
Cmax 3441.28 nM Canis lupus familiaris
Cmax 17026.63 nM Rattus norvegicus
Cmax 2568.12 nM Homo sapiens
F 95.3 % Rattus norvegicus
F 71.0 % Canis lupus familiaris
F 71.0 % Homo sapiens
F 70.0 % Homo sapiens
T1/2 2.33 hr Rattus norvegicus
T1/2 5.12 hr Canis lupus familiaris
T1/2 2.12 hr Rattus norvegicus
T1/2 7.5 hr -
T1/2 8.22 hr -
T1/2 7.45 hr -
T1/2 7.19 hr -
T1/2 7.22 hr -
T1/2 7.58 hr -
T1/2 7.4 hr Homo sapiens
T1/2 7.0 hr Homo sapiens
Tmax 0.33 hr Rattus norvegicus
Tmax 1.13 hr Canis lupus familiaris
Tmax 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DNA topoisomerase 4 subunit A IC50 = 300.0 nM 6.52 Inhibitory activity against wild type Staphylococcus aureus topoisomerase 4 16337791
Unchecked IC50 = 300.0 nM 6.52 Inhibition of Staphylococcus aureus topoisomerase 4 by decatenation assay 17228862
Unchecked IC50 = 400.0 nM 6.4 Inhibition of Staphylococcus aureus wild-type topoisomerase 4 decatenation activ... 17502409
Unchecked IC50 = 400.0 nM 6.4 Inhibition of wild-type Staphylococcus aureus topoisomerase 4-mediated decatenat... 21425851
Unchecked IC50 = 400.0 nM 6.4 Inhibition of Staphylococcus aureus topoisomerase 4 by decatenation assay 21443219
DNA gyrase IC50 = 500.0 nM 6.3 Inhibitory activity against wild type Escherichia coli gyrase 16337791
Dipeptidyl peptidase 4 IC50 = 2700.0 nM 5.57 Inhibition of DPP-4 (unknown origin) 34428715
DNA gyrase IC50 = 5600.0 nM 5.25 Inhibition of Staphylococcus aureus DNA gyrase by supercoiling assay 17228862
DNA gyrase IC50 = 5600.0 nM 5.25 Inhibition of Staphylococcus aureus wild-type DNA gyrase supercoiling activity a... 17502409
DNA gyrase IC50 = 5600.0 nM 5.25 Inhibition of wild-type Staphylococcus aureus DNA gyrase assessed as inhibition ... 21425851
DNA gyrase IC50 = 5600.0 nM 5.25 Inhibition of Staphylococcus aureus DNA gyrase by supercoiling assay 21443219
Unchecked IC50 = 9800.0 nM 5.01 Inhibition of Staphylococcus aureus wild-type topoisomerase 4 grlA S80F mutant d... 17502409
Unchecked IC50 = 9800.0 nM 5.01 Inhibition of Staphylococcus aureus topoisomerase 4 Ser80Phe mutant-mediated dec... 21425851

Literature References

PubMed DOI Target Context # Activities
17938189 10.1128/aac.01229-07 Streptococcus pneumoniae 77
17876003 10.1128/aac.00827-07 Streptococcus pneumoniae 53
17296740 10.1128/aac.00646-06 Staphylococcus aureus 22
17502409 10.1128/aac.00158-07 Staphylococcus aureus 21
20008781 10.1128/aac.01353-09 Streptococcus pneumoniae 20
17116668 10.1128/aac.01161-06 Streptococcus pneumoniae 19
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
17296740 10.1128/aac.00646-06 ADMET 12
22079379 10.1016/j.ejmech.2011.10.048 Staphylococcus aureus 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
14980680 10.1016/j.bmcl.2003.12.044 Staphylococcus aureus 11
22079379 10.1016/j.ejmech.2011.10.048 Escherichia coli 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
9357525 10.1021/jm970202e Mus musculus 8
19805559 10.1128/aac.00780-09 Streptococcus pyogenes 8
21443219 10.1021/jm2002124 Staphylococcus aureus 7
23402878 10.1016/j.bmcl.2013.01.048 Escherichia coli 7
22841282 10.1016/j.ejmech.2012.07.010 Staphylococcus aureus 7
22841282 10.1016/j.ejmech.2012.07.010 Staphylococcus epidermidis 7
22841282 10.1016/j.ejmech.2012.07.010 Escherichia coli 7

Data from ChEMBL 36 via Core Engine