Compound Detail

CHEMBL826

ENOXACIN

💊 Approved Drug

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💊 Approved Drug

CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)nc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL826
Name	ENOXACIN
Phase	Approved
Structure Type	MOL
InChI Key	IDYZIJYBMGIQMJ-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

AT-2266 CI-919 Comprecin Enoxacin Enoxacine Enoxacino Flumark NSC-629661 NSC-758416 PD 107779 PD-107779 Penetrex

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

320.3

MW (Da)

0.66

ALogP

HBA

HBD

87.5

PSA (Å²)

0.86

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1991
Availability	Discontinued
Chirality	Achiral

Routes of Administration

Oral

USAN Stem	-oxacin
USAN Year	1984

Extended Properties

Molecular Formula	C15H17FN4O3
MW	320.32
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	-1.01

Mechanism of Action

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

Indications

Bacterial Infections Amyotrophic Lateral Sclerosis Osteomyelitis

ATC Classification

J01MA04

enoxacin

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 35 meas. best 5.05

EC50 7 meas. best 4.52

Kd 2 meas. best 7.03

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
RISC-loading complex subunit TARBP2 CHEMBL2098	Kd	7.03	5.965	94.0	2
Unchecked CHEMBL612545	IC50	5.05	4.7144	9000.0	9
V-type proton ATPase subunit B, brain isoform CHEMBL5641	IC50	5.0	5.0	10000.0	1
DNA gyrase CHEMBL2094139	IC50	4.85	4.85	14000.0	1
Plasmodium falciparum CHEMBL364	IC50	4.7	4.41	20000.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.6	4.6	25010.0	1
SK-HEP1 CHEMBL614912	IC50	4.6	4.6	25030.0	1
HeLa CHEMBL399	IC50	4.59	4.59	25770.0	1
Unchecked CHEMBL612545	EC50	4.52	4.52	30000.0	2
NCI-H460 CHEMBL396	IC50	4.44	4.44	36000.0	1
Zika virus CHEMBL4296612	IC50	4.28	4.28	51990.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	29000.0	ng.hr.mL-1	Homo sapiens
CL	5.4	mL.min-1.kg-1	Homo sapiens
Cmax	11550.95	nM	Homo sapiens
F	87.38	%	Eutheria
F	89.0	%	Homo sapiens
Fu	0.8	-	Homo sapiens
MRT	6.2	hr	Homo sapiens
T1/2	5.1	hr	Homo sapiens
T1/2	2.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
RISC-loading complex subunit TARBP2	Kd	=	94.0	nM	7.03	Enhancement of His6-tagged TRBP (unknown origin) expressed in Escherichia coli B...	32672457
Unchecked	IC50	=	9000.0	nM	5.05	Inhibition of Mycobacterium tuberculosis DNA gyrase GyrB/GyrA M74I and A83S muta...	18426901
V-type proton ATPase subunit B, brain isoform	IC50	=	10000.0	nM	5.0	Inhibition of maltose binding protein-fused human V-ATPase subunit B2 binding to...	19630402
Unchecked	IC50	=	11000.0	nM	4.96	Inhibition of Mycobacterium tuberculosis DNA gyrase GyrB/GyrA A83S, S84A and I85...	18426901
RISC-loading complex subunit TARBP2	Kd	=	12560.0	nM	4.9	Binding affinity to human recombinant TRBP by SPR assay	35695407
DNA gyrase	IC50	=	14000.0	nM	4.85	Inhibition of Escherichia coli DNA gyrase GyrA/GyrB	18426901
Unchecked	IC50	=	16000.0	nM	4.8	Inhibition of Mycobacterium tuberculosis DNA gyrase GyrB/GyrA A83S mutant	18426901
Unchecked	IC50	=	16000.0	nM	4.8	Inhibition of Mycobacterium tuberculosis DNA gyrase GyrB/GyrA A83S, S84A, I85V, ...	18426901
Unchecked	IC50	=	16000.0	nM	4.8	Inhibition of Mycobacterium tuberculosis DNA gyrase GyrA M74I and A83S mutant/Gy...	18426901
Unchecked	IC50	=	19000.0	nM	4.72	Inhibition of Mycobacterium tuberculosis DNA gyrase GyrA A83S mutant/GyrB R447K ...	18426901
Plasmodium falciparum	IC50	=	20000.0	nM	4.7	Antimalarial activity against blood stage form of Plasmodium falciparum assessed...	24650715
Unchecked	IC50	=	23000.0	nM	4.64	Inhibition of Mycobacterium tuberculosis DNA gyrase GyrA/GyrB R447K mutant gene	18426901
NON-PROTEIN TARGET	IC50	=	25010.0	nM	4.6	DNDI: Cytotoxicity in Vitro, 72 hour, in rat skeletal myoblast cells	-
SK-HEP1	IC50	=	25030.0	nM	4.6	Antiproliferative activity against human SK-HEP1 cells incubated for 24 hrs by a...	34038111
HeLa	IC50	=	25770.0	nM	4.59	Antiproliferative activity against human HeLa cells assessed as increase in miR-...	34038111
Unchecked	IC50	=	30000.0	nM	4.52	Inhibition of human topoisomerase 2	31931338
Unchecked	EC50	=	30000.0	nM	4.52	Enhancement of RNA interference pathway in HEK293 cells expressing 293-EGFP and ...	32672457
Unchecked	EC50	=	30000.0	nM	4.52	Activation of miRNA (unknown origin)	30108932
NCI-H460	IC50	=	36000.0	nM	4.44	Inhibition of human NCI-H460 cell proliferation by sulphorodhamine B assay	19595598
Zika virus	IC50	=	51990.0	nM	4.28	Antiviral activity against ZIKV infected in human neural progenitor cells incuba...	32672457

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	432
17043131	10.1128/aac.00600-06	Salmonella typhimurium	44
16472241	10.2174/1570163043334794	Hepatotoxicity	18
31279292	10.1016/j.ejmech.2019.06.071	Staphylococcus aureus	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
18426901	10.1128/aac.01380-07	Unchecked	10
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
19630402	10.1021/jm900277z	NON-PROTEIN TARGET	8
31279292	10.1016/j.ejmech.2019.06.071	Pseudomonas aeruginosa	7
34038111	10.1021/acs.jmedchem.1c00018	SK-HEP1	7
3005575	10.1021/jm00153a015	DNA topoisomerase 2-beta	6
19630402	10.1021/jm900277z	Osteoclast	6
32672457	10.1021/acs.jmedchem.0c00510	Unchecked	6
3007757	10.1021/jm00154a003	Mus musculus	6
3114492	10.1021/jm00392a017	Mus musculus	6
31279292	10.1016/j.ejmech.2019.06.071	Staphylococcus epidermidis	4
18426954	10.1124/dmd.108.020479	ADMET	4
31803393	10.1039/C9MD00120D	ADMET	4
19630402	10.1021/jm900277z	ADMET	4
19752278	10.1128/aac.00631-09	Serratia marcescens	4

Data from ChEMBL 36 via Core Engine