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Compound Detail

CHEMBL850

SPARFLOXACIN
💊 Approved Drug
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💊 Approved Drug
C[C@@H]1CN(c2c(F)c(N)c3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)C[C@H](C)N1

Basic Information

ChEMBL ID CHEMBL850
Name SPARFLOXACIN
Phase Approved
Structure Type MOL
InChI Key DZZWHBIBMUVIIW-DTORHVGOSA-N
Therapeutic ✓ Yes

Known Names

AT-4140 CI-978 Esparfloxacino NSC-759641 Spara Sparfloxacin Sparfloxacine Zagam
3
Targets
17
Activities
2
Assay Types
18
PK Parameters
20
Publications
8
Known Names
2
Indications
2
Mechanisms

Molecular Properties

392.4
MW (Da)
2.08
ALogP
6
HBA
3
HBD
100.6
PSA (Ų)
0.69
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -oxacin
USAN Year 1991

Extended Properties

Molecular Formula C19H22F2N4O3
MW 392.41
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.11

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

J01MA09
sparfloxacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 16 meas. best 4.75
Ki 1 meas. best 4.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 4.75 4.58 18000.0 11
Trypanosoma brucei brucei
CHEMBL612851
IC50 4.73 4.73 18500.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 4.41 4.41 38619.4 1
Voltage-gated L-type calcium channel
CHEMBL2095229
IC50 4.05 4.05 88800.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 43000.0 ng.hr.mL-1 Mus musculus
AUC 20000.0 ng.hr.mL-1 Homo sapiens
CL 2.7 mL.min-1.kg-1 Homo sapiens
CL 2.3 mL.min-1.kg-1 Homo sapiens
CL 2.7 mL.min-1.kg-1 Homo sapiens
CL 2.7 mL.min-1.kg-1 Homo sapiens
Cmax 1911.27 nM Mus musculus
Cmax 2548.36 nM Homo sapiens
F 92.0 % Homo sapiens
F 92.0 % Homo sapiens
Fu 0.26 - Mus musculus
Fu 0.55 - Homo sapiens
Fu 0.55 - Homo sapiens
Fu 0.88 - Homo sapiens
MRT 24.0 hr Homo sapiens
T1/2 9.8 hr Mus musculus
T1/2 20.0 hr Homo sapiens
T1/2 18.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 18000.0 nM 4.75 Inhibition of human ERG current by patch clamp assay 23711922
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 18197.01 nM 4.74 Inhibition of human Potassium channel HERG expressed in mammalian cells 12873512
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 18197.01 nM 4.74 Inhibitory concentration against potassium channel HERG 15911273
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 18197.01 nM 4.74 Inhibition of human ERG expressed in CHO cells by whole cell patch clamp techniq... 18448342
Trypanosoma brucei brucei IC50 = 18500.0 nM 4.73 Antitrypanosomal activity against wild type Trypanosoma brucei brucei s427 after... 19250832
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 21700.0 nM 4.66 Binding affinity to wild type human ERG expressed in HEK293 cells assessed as in... 23711922
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 26302.68 nM 4.58 Inhibition of human voltage-gated potassium channel subunit Kv11.1 (ERG K+ chann... 15745831
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 26302.68 nM 4.58 Inhibition of human ERG in MCF7 cells 19110341
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 33600.0 nM 4.47 Binding affinity to human ERG F656A tandem dimeric mutant expressed in HEK293 ce... 23711922
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 34400.0 nM 4.46 K+ channel blocking activity in human embryonic kidney cells expressing HERG Kv1... 12190308
Voltage-gated inwardly rectifying potassium channel KCNH2 Ki = 38619.4 nM 4.41 DRUGMATRIX: Potassium Channel HERG radioligand binding (ligand: [3H] Astemizole) -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 47138.4 nM 4.33 DRUGMATRIX: Potassium Channel HERG radioligand binding (ligand: [3H] Astemizole) -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 46900.0 nM 4.33 Binding affinity to human ERG S624A tetrameric mutant expressed in HEK293 cells ... 23711922
Voltage-gated L-type calcium channel IC50 = 88800.0 nM 4.05 Inhibition of Cav1.2 current measured using QPatch automatic path clamp system i... 23812503

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 463
19164140 10.1128/aac.00822-08 Klebsiella aerogenes 62
18725440 10.1128/aac.00082-08 Streptococcus pneumoniae 38
19164140 10.1128/aac.00822-08 Klebsiella pneumoniae 34
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19414571 10.1128/aac.00023-09 Bordetella pertussis 15
19164140 10.1128/aac.00822-08 Escherichia coli 14
18644963 10.1128/aac.00026-08 Escherichia coli 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
19124662 10.1128/aac.01173-08 Staphylococcus aureus 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17145798 10.1128/aac.00414-06 Mycobacterium tuberculosis 8
20070106 10.1021/jm901371v Homo sapiens 8
20231390 10.1128/aac.00014-10 Escherichia coli 8
31803393 10.1039/C9MD00120D ADMET 7
23711922 10.1016/j.bmcl.2013.04.074 Voltage-gated inwardly rectifying potassium channel KCNH2 7
17548499 10.1128/aac.00339-07 Escherichia coli 7
17452482 10.1128/aac.00070-07 Escherichia coli 6
17276057 10.1016/j.bmcl.2007.01.038 Staphylococcus aureus 6
17382544 10.1016/j.bmcl.2007.03.004 Staphylococcus aureus 6

Data from ChEMBL 36 via Core Engine