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Compound Detail

CHEMBL9

NORFLOXACIN
💊 Approved Drug
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💊 Approved Drug
CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)cc21

Basic Information

ChEMBL ID CHEMBL9
Name NORFLOXACIN
Phase Approved
Structure Type MOL
InChI Key OGJPXUAPXNRGGI-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Baccidal Chibroxin MK-366 Norfloxacin Norfloxacine Norfloxacino Noroxin NSC-757250 Quinabic Utinor
17
Targets
58
Activities
3
Assay Types
21
PK Parameters
20
Publications
10
Known Names
8
Indications
2
Mechanisms

Molecular Properties

319.3
MW (Da)
1.27
ALogP
5
HBA
2
HBD
74.6
PSA (Ų)
0.89
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1986
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral Topical

Flags

Black Box Warning
USAN Stem -oxacin
USAN Year 1984

Extended Properties

Molecular Formula C16H18FN3O3
MW 319.34
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.97

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 Eye Infections Cystitis, Hemorrhagic Esophageal and Gastric Varices Liver Cirrhosis Peritonitis Hermanski-Pudlak Syndrome Osteomyelitis

ATC Classification

J01MA06
norfloxacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AE02
norfloxacin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 55 meas. best 7.7
Kd 2 meas. best 4.01
Ki 1 meas. best 10.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 10.05 10.05 0.1 1
GABA-A receptor; anion channel
CHEMBL1907607
IC50 7.7 6.295 20.0 2
Unchecked
CHEMBL612545
IC50 7.05 5.9982 90.0 11
DNA gyrase
CHEMBL2094139
IC50 6.22 5.2267 600.0 3
Bromodomain-containing protein 4
CHEMBL1163125
IC50 6.01 6.01 980.0 1
Cytochrome P450 2J2
CHEMBL3491
IC50 5.59 5.59 2560.0 1
L6
CHEMBL614793
IC50 5.46 5.46 3431.1 1
DNA topoisomerase 4 subunit A
CHEMBL4088
IC50 5.46 5.46 3500.0 1
HBL-100
CHEMBL614811
IC50 4.91 4.91 12430.0 1
Topoisomerase IV
CHEMBL3038508
IC50 4.9 4.9 12560.0 1
ADMET
CHEMBL612558
IC50 4.86 4.86 13800.0 1
MCF7
CHEMBL387
IC50 4.71 4.71 19370.0 1
NCI/ADR-RES
CHEMBL613829
IC50 4.7 4.7 20060.0 1
Trypanosoma brucei brucei
CHEMBL612851
IC50 4.4 4.4 39900.0 1
Plasmodium falciparum
CHEMBL364
IC50 4.27 4.2083 54000.0 12
A-431
CHEMBL614069
IC50 4.16 4.16 70000.0 1
NCI-H460
CHEMBL396
IC50 4.07 4.07 86000.0 1
Multidrug resistance protein MdtK
CHEMBL1681613
Kd 4.01 4.01 98400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6.49 - Rattus norvegicus
AUC 3.3 - Rattus norvegicus
AUC 1.9 - Rattus norvegicus
AUC 22.01 - Rattus norvegicus
AUC 8.78 - Rattus norvegicus
AUC 980.0 ng.hr.mL-1 -
AUC 1770.0 ng.hr.mL-1 -
AUC 1800.0 ng.hr.mL-1 -
AUC 6490.0 ng.hr.mL-1 Mus musculus
AUC 6490.0 ng.hr.mL-1 Mus musculus
AUC 6500.0 ng.hr.mL-1 -
AUC 2300.0 ng.hr.mL-1 -
AUC 10000.0 ng.hr.mL-1 Homo sapiens
Cmax 4697.19 nM Homo sapiens
F 62.99 % Eutheria
F 35.0 % Homo sapiens
F 35.0 % Homo sapiens
Fu 0.87 - Rattus norvegicus
Fu 0.58 - Rattus norvegicus
T1/2 3.0 hr Homo sapiens
Vd 2.9 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.09 nM 10.05 Inhibition of Escherichia coli DNA gyraseB assessed as inhibition of pBR322 supe... 20655215
GABA-A receptor; anion channel IC50 = 20.0 nM 7.7 Inhibition of [3H]muscimol binding to GABA A receptor 4-biphenylacetic acid at 1... 8388467
Unchecked IC50 = 90.0 nM 7.05 Inhibition of Escherichia coli DNA gyrase assessed as inhibition of pBR322 super... 21534606
Unchecked IC50 = 90.0 nM 7.05 Inhibition of Escherichia coli DNA gyraseB assessed as inhibition of pBR322 supe... 20655215
Unchecked IC50 = 270.0 nM 6.57 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 490.0 nM 6.31 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Unchecked IC50 = 510.0 nM 6.29 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
DNA gyrase IC50 = 600.0 nM 6.22 Inhibition of DNA gyrase supercoiling in Escherichia coli ATCC 25922 16392790
Unchecked IC50 = 880.0 nM 6.06 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
Unchecked IC50 = 890.0 nM 6.05 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Bromodomain-containing protein 4 IC50 = 980.0 nM 6.01 Inhibition of BRD4 (unknown origin) 33460833
Cytochrome P450 2J2 IC50 = 2560.0 nM 5.59 Inhibition of human recombinant CYP2J2 assessed as reduction in astemizole O-dem... 23033255
Unchecked IC50 = 2845.0 nM 5.55 PUBCHEM_BIOASSAY: High Throughput Screen to Identify Inhibitors of Mycobacterium... -
Unchecked IC50 = 3500.0 nM 5.46 Inhibition of Staphylococcus aureus DNA Topoisomerase 4-mediated decatenation of... 21534606
L6 IC50 = 3431.1 nM 5.46 Cytotoxicity against rat L6 cells assessed as inhibition of cell viability incub... 32623216
DNA topoisomerase 4 subunit A IC50 = 3500.0 nM 5.46 Inhibition of topoisomerase 4 decatenation in Staphylococcus aureus ATCC 29213 16392790
HBL-100 IC50 = 12430.0 nM 4.91 Cytotoxicity against human HBL-100 cells assessed as reduction in cell viability... 34319100
Topoisomerase IV IC50 = 12560.0 nM 4.9 Inhibition of drug-resistant Staphylococcus aureus topoisomerase 4 38944934
GABA-A receptor; anion channel IC50 = 13000.0 nM 4.89 Inhibition of [3H]muscimol binding to GABA A receptor with compound alone at 10 ... 8388467
ADMET IC50 = 13800.0 nM 4.86 Dark toxicity against human MCF7 cells assessed as decrease in cell viability by... 29673980

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
17261619 10.1128/aac.01278-06 Pseudomonas aeruginosa 93
21173174 10.1128/aac.00927-10 Escherichia coli 64
19164140 10.1128/aac.00822-08 Klebsiella aerogenes 62
17420206 10.1128/aac.00052-07 Escherichia coli 60
18725440 10.1128/aac.00082-08 Streptococcus pneumoniae 38
19223646 10.1128/aac.01087-08 Escherichia coli 34
19164140 10.1128/aac.00822-08 Klebsiella pneumoniae 34
18490500 10.1128/aac.01686-07 Escherichia coli 33
19738019 10.1128/aac.00724-09 NON-PROTEIN TARGET 28
20211899 10.1128/aac.01420-09 Escherichia coli 28
3761321 10.1021/jm00160a037 Mus musculus 22
20937787 10.1128/aac.00672-10 Streptococcus pneumoniae 22
21051535 10.1124/dmd.110.034629 ADMET 21
20876376 10.1128/aac.00719-10 Escherichia coli 20
18180352 10.1128/aac.01094-07 Proteus mirabilis 19
18838592 10.1128/aac.00665-08 Escherichia coli 19
19752278 10.1128/aac.00631-09 Serratia marcescens 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
17116660 10.1128/aac.00972-06 Streptococcus suis 18

Data from ChEMBL 36 via Core Engine