Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H17FN4O3.C6H12O7 |
Molecular Weight | 516.4742 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N=C12)N3CCNCC3
InChI
InChIKey=UQCAODSJNCBXEG-IFWQJVLJSA-N
InChI=1S/C15H17FN4O3.C6H12O7/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;7-1-2(8)3(9)4(10)5(11)6(12)13/h7-8,17H,2-6H2,1H3,(H,22,23);2-5,7-11H,1H2,(H,12,13)/t;2-,3-,4+,5-/m.1/s1
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 |
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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 |
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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 |
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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 |
---|---|---|---|---|
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: |
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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: |
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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 |
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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 |
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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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Enoxacin acute liver injury. | 1992 May |
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[The history of the development and changes of quinolone antibacterial agents]. | 2003 |
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Enoxacin trihydrate. | 2004 Apr |
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Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | 2004 Apr |
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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 |
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Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin. | 2004 Dec |
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Sensitivity and spectrum of bacterial isolates in infectious otitis externa. | 2004 Mar |
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Spectroscopic properties of various quinolone antibiotics in aqueous-organic solvent mixtures. | 2004 Nov-Dec |
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Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux. | 2004 Nov-Dec |
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[Simultaneous determination of quinolones in foods by LC/MS/MS]. | 2004 Oct |
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A novel approach to estimate in vitro antibacterial potency of Chinese medicine using a concentration-killing curve method. | 2005 |
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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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Validation of a novel HPLC sorbent material for the determination of ten quinolones in human and veterinary pharmaceutical formulations. | 2005 Dec |
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Preparation and evaluation of sustained ophthalmic gel of enoxacin. | 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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Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation. | 2005 Jul 4 |
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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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Flow-injection electrogenerated chemiluminescence determination of fluoroquinolones based on its sensitizing effect. | 2005 Jul-Oct |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Interaction study between enoxacin and fluvoxamine. | 2005 Jun |
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Direct determination of five fluoroquinolones in chicken whole blood and in veterinary drugs by HPLC. | 2005 Mar |
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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 |
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Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo. | 2005 May |
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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 |
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Separation and determination of seven fluoroquinolones by pressurized capillary electrochromatography. | 2005 Nov |
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[Determination of enoxacin in urine by synchronous fluorimetry]. | 2005 Oct |
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Bench-to-bedside review: antimicrobial utilization strategies aimed at preventing the emergence of bacterial resistance in the intensive care unit. | 2005 Oct 5 |
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Effect of fluoroquinolones on plasma glucose levels in fasted and glucose-loaded mice. | 2006 Apr |
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Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101. | 2006 Apr |
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Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA). | 2006 Apr 19 |
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Antimicrobial drug resistance, regulation, and research. | 2006 Feb |
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Genotoxic potential of quinolone antimicrobials in the in vitro comet assay and micronucleus test. | 2006 Feb 28 |
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Radiation-induced in vitro phototoxic potential of some fluoroquinolones. | 2006 Jan |
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Effects of Transcutol P on the corneal permeability of drugs and evaluation of its ocular irritation of rabbit eyes. | 2006 Jan |
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T cell-mediated hypersensitivity to quinolones: mechanisms and cross-reactivity. | 2006 Jan |
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Photophysics and photochemistry of nalidixic acid. | 2006 Jan-Feb |
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A batch chemiluminescence determination of enoxacin using a tris-(1,10-phenanthroline)ruthenium(II)-cerium(IV) system. | 2006 Jul |
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Quinolones for uncomplicated acute cystitis in women. | 2006 Jul 19 |
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[Study on interaction of caffeine and theophylline with bovine serum albumins]. | 2006 Mar |
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Electrochemiluminescence of terbium (III)-two fluoroquinolones-sodium sulfite system in aqueous solution. | 2006 May 1 |
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A new approach to quantitative NMR: fluoroquinolones analysis by evaluating the chemical shift displacements. | 2006 Oct 11 |
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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
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FK8O5WLR9H
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70480544
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85200-30-2
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104142-71-4
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NON-SPECIFIC STOICHIOMETRY | |||
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100000176176
Created by
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD