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Compound Detail

CHEMBL428

TROVAFLOXACIN
💊 Approved Drug
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💊 Approved Drug
N[C@@H]1[C@H]2CN(c3nc4c(cc3F)c(=O)c(C(=O)O)cn4-c3ccc(F)cc3F)C[C@@H]12

Basic Information

ChEMBL ID CHEMBL428
Name TROVAFLOXACIN
Phase Approved
Structure Type MOL
InChI Key WVPSKSLAZQPAKQ-CDMJZVDBSA-N
Therapeutic ✓ Yes

Known Names

CP-99219 Trovafloxacin Trovafloxacine Trovafloxacino Trovan Turvel
7
Targets
15
Activities
2
Assay Types
16
PK Parameters
20
Publications
6
Known Names
2
Indications
2
Mechanisms

Molecular Properties

416.4
MW (Da)
1.89
ALogP
6
HBA
2
HBD
101.5
PSA (Ų)
0.68
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn
USAN Stem -oxacin
USAN Year 1995

Extended Properties

Molecular Formula C20H15F3N4O3
MW 416.36
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.78

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 Osteomyelitis

ATC Classification

J01MA13
trovafloxacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 14 meas. best 6.02
Ki 1 meas. best 4.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MRC5
CHEMBL614181
IC50 6.02 6.02 960.0 1
Toxoplasma gondii
CHEMBL612888
IC50 5.7 5.61 2000.0 2
Thromboxane-A synthase
CHEMBL1835
IC50 5.39 5.39 4023.0 1
Unchecked
CHEMBL612545
IC50 4.94 4.94 11500.0 1
Plasmodium falciparum
CHEMBL364
IC50 4.75 4.5614 18000.0 7
Sodium-dependent dopamine transporter
CHEMBL238
Ki 4.31 4.31 49412.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 4.21 4.21 62191.0 1
Plasmodium yoelii yoelii
CHEMBL612328
IC50 4.13 4.13 74000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 40000.0 ng.hr.mL-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 2.3 mL.min-1.kg-1 Homo sapiens
CL 7.2 mL.min-1.kg-1 Macaca
CL 9.7 mL.min-1.kg-1 Canis lupus familiaris
CL 14.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 6004.42 nM Homo sapiens
F 88.0 % Homo sapiens
Fu 0.24 - Homo sapiens
Fu 0.24 - Homo sapiens
MRT 15.0 hr Homo sapiens
T1/2 11.0 hr Homo sapiens
T1/2 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MRC5 IC50 = 960.0 nM 6.02 In vitro inhibitory activity on MRC5 fibroblast tissue cultures inoculated with ... 15125930
Toxoplasma gondii IC50 = 2000.0 nM 5.7 Antimicrobial activity against Toxoplasma gondii 20185316
Toxoplasma gondii IC50 = 3000.0 nM 5.52 Antimicrobial activity against Toxoplasma gondii 20185316
Thromboxane-A synthase IC50 = 4023.0 nM 5.39 DRUGMATRIX: Thromboxane Synthetase enzyme inhibition (substrate: PGH2) -
Unchecked IC50 = 11500.0 nM 4.94 Inhibition of human OAT2 tv.1 variant expressed in HEK293 cells assessed as inhi... 36270005
Plasmodium falciparum IC50 = 18000.0 nM 4.75 Antiplasmodial activity against synchronized Plasmodium falciparum K1 29360043
Plasmodium falciparum IC50 = 22000.0 nM 4.66 In vitro inhibitory activity against chloroquine-resistant Plasmodium falciparum... 15125930
Plasmodium falciparum IC50 = 22000.0 nM 4.66 Antiplasmodial activity against synchronized Plasmodium falciparum CS2 29360043
Plasmodium falciparum IC50 = 33000.0 nM 4.48 Antiplasmodial activity against asynchronous Plasmodium falciparum K1 29360043
Plasmodium falciparum IC50 = 34000.0 nM 4.47 Antiplasmodial activity against asynchronous Plasmodium falciparum CS2 29360043
Plasmodium falciparum IC50 = 34000.0 nM 4.47 Antiplasmodial activity against synchronized Plasmodium falciparum 3D7 29360043
Plasmodium falciparum IC50 = 36000.0 nM 4.44 Antiplasmodial activity against asynchronous Plasmodium falciparum 3D7 29360043
Sodium-dependent dopamine transporter Ki = 49412.0 nM 4.31 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Sodium-dependent dopamine transporter IC50 = 62191.0 nM 4.21 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Plasmodium yoelii yoelii IC50 = 74000.0 nM 4.13 In vitro inhibitory activity against hepatic stages of Plasmodium yoelii yoelii ... 15125930

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 152
19332671 10.1128/aac.01424-08 Coxiella burnetii 30
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
29360043 10.1016/j.ejmech.2018.01.039 Plasmodium falciparum 8
15920768 10.1002/jps.20373 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
31803393 10.1039/C9MD00120D ADMET 6
16078842 10.1021/jm050035f No relevant target 5
16019946 10.1080/00498250400028197 ADMET 4
34861348 10.1016/j.bmcl.2021.128484 Staphylococcus aureus 4
37468498 10.1038/s41467-023-40064-9 Bile acid receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
28174104 10.1016/j.bmcl.2017.01.073 Escherichia coli 4
18299411 10.1128/aac.00035-08 Streptococcus sp. 'group B' 3
18952418 10.1016/j.bmcl.2008.10.045 Enterococcus faecalis 3
20207140 10.1016/j.bmcl.2010.02.015 Escherichia coli 3
18952418 10.1016/j.bmcl.2008.10.045 Escherichia coli 3
20207140 10.1016/j.bmcl.2010.02.015 Enterococcus faecalis 3

Data from ChEMBL 36 via Core Engine