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Compound Detail

CHEMBL4

OFLOXACIN
💊 Approved Drug
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💊 Approved Drug
CC1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4
Name OFLOXACIN
Phase Approved
Structure Type MOL
InChI Key GSDSWSVVBLHKDQ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

DL-8280 Exocin Floxin Floxin otic HOE 280 HOE-280 J01MA01 NSC-727071 NSC-758178 Ocuflox Ofloxacin Ofloxacine +5 more
11
Targets
42
Activities
3
Assay Types
30
PK Parameters
20
Publications
17
Known Names
18
Indications
1
Mechanisms

Molecular Properties

361.4
MW (Da)
1.54
ALogP
6
HBA
1
HBD
75.0
PSA (Ų)
0.87
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning
USAN Stem -oxacin
USAN Year 1984

Extended Properties

Molecular Formula C18H20FN3O4
MW 361.37
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial DNA gyrase inhibitor INHIBITOR Bacterial DNA gyrase ✓ ✓

Indications

Acne Vulgaris Bacterial Infections Bronchitis, Chronic Corneal Ulcer Eye Infections Infections Otitis Externa Conjunctivitis, Bacterial Diabetic Foot Glaucoma Glaucoma, Open-Angle Ocular Hypertension Otitis Media Otitis Media Pelvic Inflammatory Disease Urinary Tract Infections Hearing Loss Osteomyelitis

ATC Classification

J01MA01
ofloxacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AE01
ofloxacin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02AA16
ofloxacin
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS

Drug Warnings

Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
musculoskeletal toxicity
Country: United States

Activity Summary

IC50 38 meas. best 6.51
EC50 3 meas. best 5.52
Kd 1 meas. best 4.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.51 5.485 310.0 14
Chlamydia trachomatis
CHEMBL614606
 IC50 6.18 6.18 666.0 1
DNA gyrase
CHEMBL2094139
 IC50 5.82 5.82 1500.0 1
Mycolicibacterium smegmatis
CHEMBL613088
 IC50 5.76 5.65 1730.0 6
Streptococcus sp. 'group A'
CHEMBL612389
 EC50 5.52 5.52 3033.0 1
Streptokinase A
CHEMBL1293228
 EC50 5.43 5.43 3694.0 1
Streptococcus
CHEMBL612313
 EC50 5.39 5.39 4106.0 1
GABA-A receptor; anion channel
CHEMBL1907607
 IC50 4.96 4.96 11000.0 1
Albumin
CHEMBL3253
 Kd 4.92 4.92 12000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.9 4.9 12589.2 2
DNA gyrase subunit A/DNA gyrase subunit B
CHEMBL3430898
 IC50 4.55 4.55 28000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 29000.0 ng.hr.mL-1 Mus musculus
AUC 6100.0 ng.hr.mL-1 Rattus norvegicus
AUC 14100.0 ng.hr.mL-1 Homo sapiens
AUC 21200.0 ng.hr.mL-1 Homo sapiens
AUC 31400.0 ng.hr.mL-1 Homo sapiens
AUC 61000.0 ng.hr.mL-1 Homo sapiens
AUC 41200.0 ng.hr.mL-1 Homo sapiens
AUC 43500.0 ng.hr.mL-1 Homo sapiens
AUC 64000.0 ng.hr.mL-1 Homo sapiens
CL 3.5 mL.min-1.kg-1 Homo sapiens
CL 3.5 mL.min-1.kg-1 Homo sapiens
CL 0.8 mL.min-1.kg-1 Homo sapiens
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 2.65 mL.min-1.kg-1 Canis lupus familiaris
CL 4.53 mL.min-1.kg-1 Homo sapiens
CL 7.5 mL.min-1.kg-1 Macaca
CL 26.3 mL.min-1.kg-1 Rattus norvegicus
CL 14.33 mL.min-1.kg-1 Rattus norvegicus
Cmax 4704.32 nM Mus musculus
Cmax 30162.99 nM Rattus norvegicus
Cmax 4150.87 nM Homo sapiens
Cmax 6641.39 nM Homo sapiens
Cmax 8025.02 nM Homo sapiens
Cmax 6087.94 nM Homo sapiens
Cmax 9962.09 nM Homo sapiens
Cmax 12729.34 nM Homo sapiens
Cmax 13282.78 nM Homo sapiens
F 94.36 % Eutheria
F 90.0 % Homo sapiens
F 90.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 310.0 nM 6.51 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 390.0 nM 6.41 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 560.0 nM 6.25 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Chlamydia trachomatis IC50 = 666.0 nM 6.18 Antichlamydial activity against Chlamydia trachomatis serovar L2 infected in hum... 29232584
Unchecked IC50 = 800.0 nM 6.1 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
DNA gyrase IC50 = 1500.0 nM 5.82 Inhibition of Escherichia coli DNA gyrase GyrA/GyrB 18426901
Unchecked IC50 = 1730.0 nM 5.76 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Mycolicibacterium smegmatis IC50 = 1730.0 nM 5.76 Antimycobacterial activity against Mycobacterium smegmatis grown in nitrogen -li... 19786608
Mycolicibacterium smegmatis IC50 = 1730.0 nM 5.76 Antimycobacterial activity against Mycobacterium smegmatis grown in nitrogen -li... 19786608
Mycolicibacterium smegmatis IC50 = 2030.0 nM 5.69 Antimycobacterial activity against Mycobacterium smegmatis grown in Luria-Bertan... 19786608
Mycolicibacterium smegmatis IC50 = 2030.0 nM 5.69 Antimycobacterial activity against Mycobacterium smegmatis grown in Luria-Bertan... 19786608
Streptococcus sp. 'group A' EC50 = 3033.0 nM 5.52 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Unchecked IC50 = 3000.0 nM 5.52 Inhibition of Mycobacterium tuberculosis DNA gyrase GyrB/GyrA M74I and A83S muta... 18426901
Mycolicibacterium smegmatis IC50 = 3130.0 nM 5.5 Antimycobacterial activity against Mycobacterium smegmatis grown in carbon-limit... 19786608
Mycolicibacterium smegmatis IC50 = 3130.0 nM 5.5 Antimycobacterial activity against Mycobacterium smegmatis grown in carbon-limit... 19786608
Streptokinase A EC50 = 3694.0 nM 5.43 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Unchecked IC50 = 4000.0 nM 5.4 Inhibition of Mycobacterium tuberculosis DNA gyrase GyrA A83S mutant/GyrB R447K ... 18426901
Streptococcus EC50 = 4106.0 nM 5.39 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Unchecked IC50 = 7000.0 nM 5.16 Inhibition of Mycobacterium tuberculosis DNA gyrase GyrB/GyrA A83S mutant 18426901
Unchecked IC50 = 7000.0 nM 5.16 Inhibition of Mycobacterium tuberculosis DNA gyrase GyrB/GyrA A83S, S84A, I85V, ... 18426901

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
19687244 10.1128/aac.00287-09 Mycobacterium tuberculosis 80
17908946 10.1128/aac.00294-07 Salmonella enterica subsp. enterica 61
19332671 10.1128/aac.01424-08 Coxiella burnetii 30
19805572 10.1128/aac.00532-09 Clostridioides difficile 28
19721073 10.1128/aac.00541-09 Mycobacterium tuberculosis 23
18426901 10.1128/aac.01380-07 Unchecked 22
16472241 10.2174/1570163043334794 Hepatotoxicity 18
18694945 10.1128/aac.00464-08 Pseudomonas aeruginosa 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19596880 10.1128/aac.00121-09 NON-PROTEIN TARGET 13
- 10.1039/C5MD00589B Mycobacterium tuberculosis 12
19786608 10.1128/aac.00803-09 Mycolicibacterium smegmatis 12
20713679 10.1128/aac.00661-10 Mycobacterium tuberculosis 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
29360043 10.1016/j.ejmech.2018.01.039 Plasmodium falciparum 11
19687238 10.1128/aac.00477-09 Chlamydia trachomatis 11
18070975 10.1128/aac.01095-07 Mycobacterium leprae 11
18426901 10.1128/aac.01380-07 NON-PROTEIN TARGET 10
18362191 10.1128/aac.01150-07 Staphylococcus saprophyticus 10

Data from ChEMBL 36 via Core Engine