Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H17FN4O3 |
Molecular Weight | 320.3195 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCn1cc(c(=O)c2cc(c(nc21)N3CCNCC3)F)C(=O)O
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 | 320.3195 |
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 Date6.9413759E11 |
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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 Date6.9413759E11 |
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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 Date6.9413759E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
4.9 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 |
|
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 |
|
4.5 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 |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg single, oral Highest studied dose |
unhealthy, 41.9 years n = 79 Health Status: unhealthy Condition: cystitis Age Group: 41.9 years Sex: M+F Population Size: 79 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 n = 75 Health Status: unhealthy Condition: cystitis Age Group: 43.8 years Sex: M+F Population Size: 75 Sources: |
|
600 mg 3 times / day multiple, oral (max) Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, adult n = 20060 Health Status: unhealthy Condition: Gram-negative urinary tract pathogens Age Group: adult Sex: M+F Population Size: 20060 Sources: |
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 (max) Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, adult n = 20060 Health Status: unhealthy Condition: Gram-negative urinary tract pathogens Age Group: adult Sex: M+F Population Size: 20060 Sources: |
Gastrointestinal disorders | 1.3% | 600 mg 3 times / day multiple, oral (max) Highest studied dose Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, adult n = 20060 Health Status: unhealthy Condition: Gram-negative urinary tract pathogens Age Group: adult Sex: M+F Population Size: 20060 Sources: |
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 |
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Sources: https://pubmed.ncbi.nlm.nih.gov/7503804/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Assessment of temafloxacin neurotoxicity in rodents. | 1991 Dec 30 |
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Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs. | 1991 Jun |
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Interaction of the new quinolone antibacterial agent levofloxacin with fenbufen in mice. | 1992 Mar |
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[Effects of drugs on the convulsions induced by the combination of a new quinolone antimicrobial, enoxacin, and a nonsteroidal anti-inflammatory drug, fenbufen, in mice]. | 1992 Oct |
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Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions. | 2001 |
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A pharmacokinetic/pharmacodynamic approach to show that not all fluoroquinolones exhibit similar sensitivity toward the proconvulsant effect of biphenyl acetic acid in rats. | 2001 Dec |
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Quinolones and false-positive urine screening for opiates by immunoassay technology. | 2001 Dec 26 |
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Selective separation and simultaneous determination of trace levels of five types of fluorinated quinolone drugs by thin-layer chromatography/fluorescence densitometry. | 2001 May-Jun |
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Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones. | 2001 Nov-Dec |
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Is more than one quinolone needed in clinical practice? | 2001 Sep |
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Multiresidue determination of (fluoro)quinolone antibiotics in swine kidney using liquid chromatography-tandem mass spectrometry. | 2002 Apr 5 |
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Identification and characterization of a novel efflux-related multidrug resistance phenotype in Staphylococcus aureus. | 2002 Dec |
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The expanding role of fluoroquinolones. | 2002 Jul 8 |
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Possible gatifloxacin-induced fulminant hepatic failure. | 2002 Jul-Aug |
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[Drug interactions between nonsteroidal anti-inflammatory drug and pazufloxacin mesilate, a new quinolone antibacterial agent for intravenous use: convulsions in mice after intravenous or intracerebroventricular administration]. | 2002 Jun |
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[Phototoxicity studies of pazufloxacin mesilate, a novel parenteral quinolone antimicrobial agent--in vitro and in vivo studies]. | 2002 Jun |
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[The history of the development and changes of quinolone antibacterial agents]. | 2003 |
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[Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital]. | 2003 Aug |
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Pharmacological evaluation of garenoxacin, a novel des-F(6)-quinolone antimicrobial agent: effects on the central nervous system. | 2003 Feb |
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Dead bugs don't mutate: susceptibility issues in the emergence of bacterial resistance. | 2003 Jan |
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Interference-free analysis using three-way fluorescence data and the parallel factor model. Determination of fluoroquinolone antibiotics in human serum. | 2003 Jun 1 |
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Enoxacin trihydrate. | 2004 Apr |
|
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 Apr-Jun |
|
Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin. | 2004 Dec |
|
Effects of eight antibacterial agents on cell survival and expression of epithelial-cell- or cell-adhesion-related genes in human gingival epithelial cells. | 2004 Feb |
|
Sensitivity and spectrum of bacterial isolates in infectious otitis externa. | 2004 Mar |
|
Spectroscopic properties of various quinolone antibiotics in aqueous-organic solvent mixtures. | 2004 Nov-Dec |
|
Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux. | 2004 Nov-Dec |
|
A novel approach to estimate in vitro antibacterial potency of Chinese medicine using a concentration-killing curve method. | 2005 |
|
Determination of fluoroquinolones in edible animal tissue samples by high performance liquid chromatography after solid phase extraction. | 2005 Apr |
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Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods. | 2005 Apr 4 |
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HPLC determination of enoxacin, ciprofloxacin, norfloxacin and ofloxacin with photoinduced fluorimetric (PIF) detection and multiemission scanning: application to urine and serum. | 2005 Aug 5 |
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Selective action of fluoroquinolones against intracellular amastigotes of Leishmania (Viannia) panamensis in vitro. | 2005 Dec |
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Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice. | 2005 Jan 10 |
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Induced and photoinduced DNA damage by quinolones: ciprofloxacin, ofloxacin and nalidixic acid determined by comet assay. | 2005 Jul-Aug |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Direct determination of five fluoroquinolones in chicken whole blood and in veterinary drugs by HPLC. | 2005 Mar |
|
Antibacterial studies, DNA oxidative cleavage, and crystal structures of Cu(II) and Co(II) complexes with two quinolone family members, ciprofloxacin and enoxacin. | 2005 Mar |
|
Fluoroquinolone-resistant Campylobacter isolates from conventional and antibiotic-free chicken products. | 2005 May |
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Susceptibility and resistance genes to fluoroquinolones in methicillin-resistant Staphylococcus aureus isolated in 2002. | 2005 May |
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Vibrational spectroscopic characterization of fluoroquinolones. | 2005 May |
|
Effect of fluoroquinolones on plasma glucose levels in fasted and glucose-loaded mice. | 2006 Apr |
|
Radiation-induced in vitro phototoxic potential of some fluoroquinolones. | 2006 Jan |
|
T cell-mediated hypersensitivity to quinolones: mechanisms and cross-reactivity. | 2006 Jan |
|
Photophysics and photochemistry of nalidixic acid. | 2006 Jan-Feb |
|
A batch chemiluminescence determination of enoxacin using a tris-(1,10-phenanthroline)ruthenium(II)-cerium(IV) system. | 2006 Jul |
|
Quinolones for uncomplicated acute cystitis in women. | 2006 Jul 19 |
|
[Study on interaction of caffeine and theophylline with bovine serum albumins]. | 2006 Mar |
|
A new approach to quantitative NMR: fluoroquinolones analysis by evaluating the chemical shift displacements. | 2006 Oct 11 |
|
Induction of keratinocyte apoptosis by photosensitizing chemicals plus UVA. | 2007 Feb |
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
Edited
Fri Jun 25 21:51:50 UTC 2021
by
admin
on
Fri Jun 25 21:51:50 UTC 2021
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Record UNII |
325OGW249P
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/15/1459
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WHO-VATC |
QJ01MA04
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NCI_THESAURUS |
C795
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WHO-ATC |
J01MA04
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1013
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D015365
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74011-58-8
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CHEMBL826
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5351
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325OGW249P
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C65512
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ENOXACIN
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DB00467
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Enoxacin
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SUB06540MIG
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M4911
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |