Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H17FN4O3 |
| Molecular Weight | 320.3189 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN1C=C(C(O)=O)C(=O)C2=C1N=C(N3CCNCC3)C(F)=C2
InChI
InChIKey=IDYZIJYBMGIQMJ-UHFFFAOYSA-N
InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
| Molecular Formula | C15H17FN4O3 |
| Molecular Weight | 320.3189 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6226242 | https://www.ncbi.nlm.nih.gov/pubmed/8429114 | https://www.ncbi.nlm.nih.gov/pubmed/8494374
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6226242 | https://www.ncbi.nlm.nih.gov/pubmed/8429114 | https://www.ncbi.nlm.nih.gov/pubmed/8494374
Enoxacin is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Enoxacin is bactericidal drugs, eradicating bacteria by interfering with DNA replication. Like other fluoroquinolones, enoxacin functions by inhibiting bacterial DNA gyrase and topoisomerase IV. The inhibition of these enzymes prevents bacterial DNA replication, transcription, repair and recombination. Enoxacin is active against many Gram-positive bacteria. After oral administration enoxacin is rapidly and well absorbed from the gastrointestinal tract. The antibiotic is widely distributed throughout the body and in the different biological tissues. Tissue concentrations often exceed serum concentrations. The binding of enoxacin to serum proteins is 35 to 40%. The serum elimination half-life, in subjects with normal renal function, is approximately 6 hours. Approximately 60% of an orally administered dose is excreted in the urine as unchanged drug within 24 hours. Enoxacin, like other fluoroquinolones, is known to trigger seizures or lower the seizure threshold. The compound should not be administered to patients with epilepsy or a personal history of previous convulsive attacks as may promote the onset of these disorders.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6226242
Curator's Comment: Enoxacin is a new pyridonecarboxylic acid derivative synthesized by Matsumoto et al.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363077 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18813225 |
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Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9341164 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | PENETREX Approved UseINDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae. Launch Date1991 |
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| Curative | PENETREX Approved UseINDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae. Launch Date1991 |
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| Curative | PENETREX Approved UseINDICATIONS AND USAGE. Uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae. Uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis*, or Staphylococcus saprophyticus. Complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae. Launch Date1991 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.83 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.58 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
800 mg single, intravenous dose: 800 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.02 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.8 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.8 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162904 |
400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENOXACIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
0.7 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162904 |
400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
4-OXO-ENOXACIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
7.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162904 |
600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENOXACIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
7.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162904 |
600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
4-OXO-ENOXACIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.35 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
29.08 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
800 mg single, intravenous dose: 800 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.67 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
25.75 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
800 mg single, intravenous dose: 800 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162901 |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162904 |
400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENOXACIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162904 |
600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ENOXACIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3162904 |
600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
4-OXO-ENOXACIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
600 mg single, oral Highest studied dose |
unhealthy, 41.9 years Health Status: unhealthy Age Group: 41.9 years Sex: M+F Sources: |
|
200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: |
unhealthy, 43.8 years Health Status: unhealthy Age Group: 43.8 years Sex: M+F Sources: |
|
600 mg 3 times / day multiple, oral Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, adult |
Other AEs: Gastrointestinal disorders, Epidermal and dermal conditions... Other AEs: Gastrointestinal disorders (1.3%) Sources: Epidermal and dermal conditions (0.4%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Epidermal and dermal conditions | 0.4% | 600 mg 3 times / day multiple, oral Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, adult |
| Gastrointestinal disorders | 1.3% | 600 mg 3 times / day multiple, oral Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, adult |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
no | |||
| no | ||||
| yes [Inhibition 250 uM] | yes (co-administration study) Comment: enoxacin caused a 6-fold decrease in caffeine clearance |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Induction of keratinocyte apoptosis by photosensitizing chemicals plus UVA. | 2007-02 |
|
| A new approach to quantitative NMR: fluoroquinolones analysis by evaluating the chemical shift displacements. | 2006-10-11 |
|
| Quinolones for uncomplicated acute cystitis in women. | 2006-07-19 |
|
| A batch chemiluminescence determination of enoxacin using a tris-(1,10-phenanthroline)ruthenium(II)-cerium(IV) system. | 2006-07 |
|
| Electrochemiluminescence of terbium (III)-two fluoroquinolones-sodium sulfite system in aqueous solution. | 2006-05-01 |
|
| Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA). | 2006-04-19 |
|
| Effect of fluoroquinolones on plasma glucose levels in fasted and glucose-loaded mice. | 2006-04 |
|
| Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101. | 2006-04 |
|
| [Study on interaction of caffeine and theophylline with bovine serum albumins]. | 2006-03 |
|
| Genotoxic potential of quinolone antimicrobials in the in vitro comet assay and micronucleus test. | 2006-02-28 |
|
| Antimicrobial drug resistance, regulation, and research. | 2006-02 |
|
| Radiation-induced in vitro phototoxic potential of some fluoroquinolones. | 2006-01 |
|
| Effects of Transcutol P on the corneal permeability of drugs and evaluation of its ocular irritation of rabbit eyes. | 2006-01 |
|
| T cell-mediated hypersensitivity to quinolones: mechanisms and cross-reactivity. | 2006-01 |
|
| Selective action of fluoroquinolones against intracellular amastigotes of Leishmania (Viannia) panamensis in vitro. | 2005-12 |
|
| Validation of a novel HPLC sorbent material for the determination of ten quinolones in human and veterinary pharmaceutical formulations. | 2005-12 |
|
| Preparation and evaluation of sustained ophthalmic gel of enoxacin. | 2005-12 |
|
| Separation and determination of seven fluoroquinolones by pressurized capillary electrochromatography. | 2005-11 |
|
| Bench-to-bedside review: antimicrobial utilization strategies aimed at preventing the emergence of bacterial resistance in the intensive care unit. | 2005-10-05 |
|
| [Determination of enoxacin in urine by synchronous fluorimetry]. | 2005-10 |
|
| Flow-injection electrogenerated chemiluminescence determination of fluoroquinolones based on its sensitizing effect. | 2005-09-01 |
|
| Photophysics and photochemistry of nalidixic acid. | 2005-08-19 |
|
| HPLC determination of enoxacin, ciprofloxacin, norfloxacin and ofloxacin with photoinduced fluorimetric (PIF) detection and multiemission scanning: application to urine and serum. | 2005-08-05 |
|
| Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation. | 2005-07-04 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Interaction study between enoxacin and fluvoxamine. | 2005-06 |
|
| Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo. | 2005-05 |
|
| Fluoroquinolone-resistant Campylobacter isolates from conventional and antibiotic-free chicken products. | 2005-05 |
|
| Susceptibility and resistance genes to fluoroquinolones in methicillin-resistant Staphylococcus aureus isolated in 2002. | 2005-05 |
|
| Vibrational spectroscopic characterization of fluoroquinolones. | 2005-05 |
|
| Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods. | 2005-04-04 |
|
| Determination of fluoroquinolones in edible animal tissue samples by high performance liquid chromatography after solid phase extraction. | 2005-04 |
|
| Direct determination of five fluoroquinolones in chicken whole blood and in veterinary drugs by HPLC. | 2005-03 |
|
| Antibacterial studies, DNA oxidative cleavage, and crystal structures of Cu(II) and Co(II) complexes with two quinolone family members, ciprofloxacin and enoxacin. | 2005-03 |
|
| Induced and photoinduced DNA damage by quinolones: ciprofloxacin, ofloxacin and nalidixic acid determined by comet assay. | 2005-02-05 |
|
| Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice. | 2005-01-10 |
|
| A novel approach to estimate in vitro antibacterial potency of Chinese medicine using a concentration-killing curve method. | 2005 |
|
| Spectroscopic properties of various quinolone antibiotics in aqueous-organic solvent mixtures. | 2004-12-30 |
|
| Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin. | 2004-12 |
|
| Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux. | 2004-11-16 |
|
| [Simultaneous determination of quinolones in foods by LC/MS/MS]. | 2004-10 |
|
| Comparative evaluation of antiproliferative activity and induction of apoptosis by some fluoroquinolones with a human non-small cell lung cancer cell line in culture. | 2004-07-13 |
|
| Enoxacin trihydrate. | 2004-04 |
|
| Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | 2004-04 |
|
| Sensitivity and spectrum of bacterial isolates in infectious otitis externa. | 2004-03 |
|
| [The history of the development and changes of quinolone antibacterial agents]. | 2003 |
|
| Enoxacin acute liver injury. | 1992-05 |
|
| Interaction of the new quinolone antibacterial agent levofloxacin with fenbufen in mice. | 1992-03 |
|
| Assessment of temafloxacin neurotoxicity in rodents. | 1991-12-30 |
|
| Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs. | 1991-06 |
Sample Use Guides
Enoxacin should be taken at least one hour before or at least two hours after a meal. For treatment uncomplicated urethral or cervical gonorrhea: 400 mg single dose. For treatment uncomplicated urinary tract infections 200 mg q12h for 7 days. For treatment complicated urinary tract infections: 400 mg q12h for 14 days. Dosage should be adjusted in patients with a creatinine clearance value of 30 mL/min/1.73 m 2 or less.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6226242
The in vitro antibacterial activity of AT-2266 (Enoxacin ) was tested by the determination of minimal bactericidal concentrations (MBCs) and the reduction of viable cells during exposure to the drug for 24 h. MIC90s of AT-2266 for P. aeruginosa resistant to gentamicin and Enterobacteriaceae resistant to nalidixic acid were 3.13 and 12.5 mkg/ml, respectively
| Substance Class |
Chemical
Created
by
admin
on
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Wed Apr 02 09:59:21 GMT 2025
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on
Wed Apr 02 09:59:21 GMT 2025
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| Record UNII |
325OGW249P
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Validated (UNII)
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EU-Orphan Drug |
EU/3/15/1459
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QJ01MA04
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C795
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J01MA04
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Enoxacin
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ACTIVE MOIETY |