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Compound Detail

CHEMBL31

GATIFLOXACIN
💊 Approved Drug
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💊 Approved Drug
COc1c(N2CCNC(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL31
Name GATIFLOXACIN
Phase Approved
Structure Type MOL
InChI Key XUBOMFCQGDBHNK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

AM-1155 BMS-206584-01 BMS-20658401 Gatiflo Gatifloxacin Gatifloxacin (sesquihydrate) Gatifloxacin anhydrous Gatifloxacin hydrate Gatifloxacin sesquihydrate Gatifloxacine Gatifloxacino NSC-758701 +5 more
12
Targets
30
Activities
3
Assay Types
30
PK Parameters
20
Publications
17
Known Names
8
Indications
2
Mechanisms

Molecular Properties

375.4
MW (Da)
1.98
ALogP
6
HBA
2
HBD
83.8
PSA (Ų)
0.85
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral Topical

Flags

Withdrawn
USAN Stem -oxacin
USAN Year 1997

Extended Properties

Molecular Formula C19H22FN3O4
MW 375.40
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.22

Mechanism of Action

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

Indications

Bacterial Infections Conjunctivitis, Bacterial Eye Infections Infections Tuberculosis Corneal Ulcer Cataract Osteomyelitis

ATC Classification

J01MA16
gatifloxacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AE06
gatifloxacin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Withdrawn
gastrointestinal toxicity
Increased risk of dysglycemia
Country: United States   Year: 2006
Withdrawn
gastrointestinal toxicity
Increased risk of dysglycemia
Country: United States   Year: 2006

Activity Summary

IC50 24 meas. best 6.54
EC50 3 meas. best 6.18
Ki 3 meas. best 5.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.54 6.0 290.0 6
DNA gyrase
CHEMBL2094139
 IC50 6.3 6.3 500.0 2
Streptococcus sp. 'group A'
CHEMBL612389
 EC50 6.18 6.18 660.0 1
Streptokinase A
CHEMBL1293228
 EC50 6.17 6.17 668.0 1
Streptococcus
CHEMBL612313
 EC50 5.96 5.96 1092.0 1
DNA topoisomerase 4 subunit A
CHEMBL4088
 IC50 5.92 5.92 1200.0 1
Dual specificity protein kinase CLK4
CHEMBL4203
 Ki 5.4 5.4 3981.1 1
Serine/threonine-protein kinase D3
CHEMBL2595
 Ki 5.1 5.1 7943.3 1
Dual specificity protein kinase CLK2
CHEMBL4225
 Ki 5.1 5.1 7943.3 1
DNA gyrase subunit A
CHEMBL4165
 IC50 5.03 4.6467 9400.0 3
MRC5
CHEMBL614181
 IC50 4.9 4.9 12700.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.54 4.54 29000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 30000.0 ng.hr.mL-1 Homo sapiens
AUC 33000.0 ng.hr.mL-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 81.0 ml/min Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
Cmax 47948.85 nM Mus musculus
Cmax 10655.3 nM Homo sapiens
Cmax 9057.01 nM Homo sapiens
Cmax 9057.01 nM Homo sapiens
Cmax 10122.54 nM Homo sapiens
F 96.0 % Homo sapiens
F 96.0 % Homo sapiens
F 96.0 % Homo sapiens
Fu 0.8 - Homo sapiens
Fu 0.8 - Homo sapiens
MRT 11.0 hr Homo sapiens
T1/2 7.65 hr -
T1/2 8.16 hr -
T1/2 8.65 hr -
T1/2 7.57 hr -
T1/2 8.01 hr -
T1/2 0.6 hr Mus musculus
T1/2 9.0 hr Homo sapiens
T1/2 10.0 hr Homo sapiens
T1/2 6.5 hr Homo sapiens
T1/2 6.5 hr Homo sapiens
T1/2 12.0 hr Homo sapiens
Tmax 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 290.0 nM 6.54 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 440.0 nM 6.36 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
DNA gyrase IC50 = 500.0 nM 6.3 Inhibitory activity against wild type Escherichia coli gyrase 16337791
DNA gyrase IC50 = 500.0 nM 6.3 Inhibition of Escherichia coli gyrase 17064062
Unchecked IC50 = 580.0 nM 6.24 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Streptococcus sp. 'group A' EC50 = 660.0 nM 6.18 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptokinase A EC50 = 668.0 nM 6.17 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Unchecked IC50 = 1050.0 nM 5.98 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
Streptococcus EC50 = 1092.0 nM 5.96 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Unchecked IC50 = 1100.0 nM 5.96 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
DNA topoisomerase 4 subunit A IC50 = 1200.0 nM 5.92 Inhibitory activity against wild type Staphylococcus aureus topoisomerase 4 16337791
Dual specificity protein kinase CLK4 Ki = 3981.07 nM 5.4 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Dual specificity protein kinase CLK2 Ki = 7943.28 nM 5.1 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Serine/threonine-protein kinase D3 Ki = 7943.28 nM 5.1 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
DNA gyrase subunit A IC50 = 9400.0 nM 5.03 Inhibition of DNA supercoiling activity of wild type Mycobacterium tuberculosis ... 20516287
Unchecked IC50 = 12000.0 nM 4.92 Inhibition of Plasmodium falciparum NF54 Gyrase B 38171145
MRC5 IC50 = 12700.0 nM 4.9 In vitro inhibitory activity on MRC5 fibroblast tissue cultures inoculated with ... 15125930
DNA gyrase subunit A IC50 = 28000.0 nM 4.55 Inhibition of DNA supercoiling activitysof Mycobacterium tuberculosis DNA gyrase... 20516287
Plasmodium falciparum IC50 = 29000.0 nM 4.54 In vitro inhibitory activity against chloroquine-resistant Plasmodium falciparum... 15125930
DNA gyrase subunit A IC50 = 44000.0 nM 4.36 Inhibition of DNA supercoiling activity of Mycobacterium tuberculosis DNA gyrase... 20516287

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
19364867 10.1128/aac.01252-08 Clostridioides difficile 83
19687244 10.1128/aac.00287-09 Mycobacterium tuberculosis 80
17938189 10.1128/aac.01229-07 Streptococcus pneumoniae 77
17908946 10.1128/aac.00294-07 Salmonella enterica subsp. enterica 63
19307366 10.1128/aac.01531-08 Streptococcus pneumoniae 55
17043131 10.1128/aac.00600-06 Salmonella typhimurium 44
17562807 10.1128/aac.01582-06 Clostridioides difficile 34
19738019 10.1128/aac.00724-09 NON-PROTEIN TARGET 28
18490505 10.1128/aac.01466-07 Staphylococcus aureus 27
17116666 10.1128/aac.01150-06 Streptococcus pneumoniae 26
17043111 10.1128/aac.00395-06 PC-3 24
17296740 10.1128/aac.00646-06 Staphylococcus aureus 23
17116668 10.1128/aac.01161-06 Streptococcus pneumoniae 19
18838592 10.1128/aac.00665-08 Escherichia coli 19
19451290 10.1128/aac.00176-09 Streptococcus pneumoniae 16
19506065 10.1128/aac.00418-09 NON-PROTEIN TARGET 16
17470656 10.1128/aac.00143-07 Escherichia coli 15
19414571 10.1128/aac.00023-09 Bordetella pertussis 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14

Data from ChEMBL 36 via Core Engine