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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
Structure of ENOXACIN

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)

HIDE SMILES / InChI

Description
Curator's Comment:: 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

Curator's Comment:: Enoxacin is a new pyridonecarboxylic acid derivative synthesized by Matsumoto et al.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PENETREX

Approved Use

INDICATIONS 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 Date

694137600000
Curative
PENETREX

Approved Use

INDICATIONS 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 Date

694137600000
Curative
PENETREX

Approved Use

INDICATIONS 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 Date

694137600000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.4 mg/L
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
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
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
25.75 mg × h/L
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
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
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
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
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
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
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
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

Doses

DosePopulationAdverse events​
600 mg single, oral
Highest studied dose
dose: 600 mg
route: oral
experiment_type: single
dose_type: Highest studied dose
co-adm with
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/2764538/
    unhealthy, 41.9 years
    population: unhealthy
    age: 41.9 years
    sex: M+F
    food_status:
    n:
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/2764538/
    200 mg 2 times / day steady, oral
    Recommended
    dose: 200 mg 2 times / day
    route: oral
    experiment_type: steady
    dose_type: Recommended
    co-adm with
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/2764538/
      unhealthy, 43.8 years
      population: unhealthy
      age: 43.8 years
      sex: M+F
      food_status:
      n:
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/2764538/
      600 mg 3 times / day multiple, oral
      Highest studied dose
      dose: 600 mg 3 times / day
      route: oral
      experiment_type: multiple
      dose_type: Highest studied dose
      co-adm with
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/8741236/
        unhealthy, adult
        population: unhealthy
        age: adult
        sex: M+F
        food_status:
        n:
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/8741236/
        Other AEs: Gastrointestinal disorders, Epidermal and dermal conditions...
        Other AEs:
        Gastrointestinal disorders (3 times / day)
        Epidermal and dermal conditions (3 times / day)

        data_source:
        https://pubmed.ncbi.nlm.nih.gov/8741236/
        AEs

        AEs

        AESignificanceDosePopulation
        Epidermal and dermal conditions 0.4%
        600 mg 3 times / day multiple, oral
        Highest studied dose
        dose: 600 mg 3 times / day
        route: oral
        experiment_type: multiple
        dose_type: Highest studied dose
        co-adm with
          data_source:
          https://pubmed.ncbi.nlm.nih.gov/8741236/
          unhealthy, adult
          population:
          age:
          sex:
          food_status:
          n:
          data_source:
          https://pubmed.ncbi.nlm.nih.gov/8741236/
          Gastrointestinal disorders 1.3%
          600 mg 3 times / day multiple, oral
          Highest studied dose
          dose: 600 mg 3 times / day
          route: oral
          experiment_type: multiple
          dose_type: Highest studied dose
          co-adm with
            data_source:
            https://pubmed.ncbi.nlm.nih.gov/8741236/
            unhealthy, adult
            population:
            age:
            sex:
            food_status:
            n:
            data_source:
            https://pubmed.ncbi.nlm.nih.gov/8741236/
            PubMed

            PubMed

            TitleDatePubMed
            Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs.
            1991 Jun
            Enoxacin acute liver injury.
            1992 May
            [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
            Repeated treatment with quinolones potentiates the seizures induced by aminophylline in genetically epilepsy-prone rats.
            1992 Sep
            Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions.
            2001
            Evidence of different profiles of side effects and drug-drug interactions among the quinolones--the pharmacokinetic standpoint.
            2001
            Comparison of side effects of levofloxacin versus other fluoroquinolones.
            2001
            Inhibitory effect of quinolone antimicrobial and nonsteroidal anti-inflammatory drugs on a medium chain acyl-CoA synthetase.
            2001 Aug 1
            Quinolones and false-positive urine screening for opiates by immunoassay technology.
            2001 Dec 26
            Polysaccharide synthesis as a carbon dissipation mechanism in metabolically uncoupled Xanthomonas campestris cells.
            2001 Jul 26
            Selective separation and simultaneous determination of trace levels of five types of fluorinated quinolone drugs by thin-layer chromatography/fluorescence densitometry.
            2001 May-Jun
            Biphenylacetic acid enhances the antagonistic action of fluoroquinolones on the GABA(A)-mediated responses of the isolated guinea-pig ileum.
            2001 Sep
            Possible involvement of P-glycoprotein in the biliary excretion of grepafloxacin.
            2002 Mar
            Antituberculosis agents. III. In vitro evaluation of antimycobacterial activity and cytotoxicity of some N-piperazinyl quinolone derivatives.
            2002 May-Jun
            Laser flash photolysis study of photoionization in fluoroquinolones.
            2002 Nov
            [The history of the development and changes of quinolone antibacterial agents].
            2003
            [Synthesis and antibacterial activity of pyridonecarboxylic acid derivatives containing 2-methyl-5-nitroimidazol].
            2003 Apr
            [Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital].
            2003 Aug
            Binding characteristics of fluoroquinolones to synthetic levodopa melanin.
            2003 Aug
            Corneal and scleral permeability of quinolones--a pharmacokinetics study.
            2003 Dec
            Effects of anti-inflammatory drugs on convulsant activity of quinolones: a comparative study of drug interaction between quinolones and anti-inflammatory drugs.
            2003 Dec
            A randomized controlled trial (volunteer study) of sitafloxacin, enoxacin, levofloxacin and sparfloxacin phototoxicity.
            2003 Dec
            Pharmacological evaluation of garenoxacin, a novel des-F(6)-quinolone antimicrobial agent: effects on the central nervous system.
            2003 Feb
            Interference-free analysis using three-way fluorescence data and the parallel factor model. Determination of fluoroquinolone antibiotics in human serum.
            2003 Jun 1
            Aetiology of shigellosis in northern Pakistan.
            2003 Mar
            Direct determination of four fluoroquinolones, enoxacin, norfloxacin, ofloxacin, and ciprofloxacin, in pharmaceuticals and blood serum by HPLC.
            2003 Mar
            Relationship between extent of inhibition and inhibitor dose: literature evaluation based on the metabolism and transport drug interaction database.
            2003 Oct
            [Analysis of the response factors of different quinolones detected by evaporative light-scattering detector].
            2003 Sep
            Synthesis and in vitro antibacterial evaluation of N-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-yl] piperazinyl quinolones.
            2003 Sep
            Enoxacin trihydrate.
            2004 Apr
            Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
            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
            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
            Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux.
            2004 Nov-Dec
            [Simultaneous determination of quinolones in foods by LC/MS/MS].
            2004 Oct
            Preparation and evaluation of sustained ophthalmic gel of enoxacin.
            2005 Dec
            Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice.
            2005 Jan 10
            Flow-injection electrogenerated chemiluminescence determination of fluoroquinolones based on its sensitizing effect.
            2005 Jul-Oct
            Prediction of genotoxicity of chemical compounds by statistical learning methods.
            2005 Jun
            Interaction study between enoxacin and fluvoxamine.
            2005 Jun
            Direct determination of five fluoroquinolones in chicken whole blood and in veterinary drugs by HPLC.
            2005 Mar
            Vibrational spectroscopic characterization of fluoroquinolones.
            2005 May
            Separation and determination of seven fluoroquinolones by pressurized capillary electrochromatography.
            2005 Nov
            Bench-to-bedside review: antimicrobial utilization strategies aimed at preventing the emergence of bacterial resistance in the intensive care unit.
            2005 Oct 5
            Genotoxic potential of quinolone antimicrobials in the in vitro comet assay and micronucleus test.
            2006 Feb 28
            [Study on interaction of caffeine and theophylline with bovine serum albumins].
            2006 Mar
            Electrochemiluminescence of terbium (III)-two fluoroquinolones-sodium sulfite system in aqueous solution.
            2006 May 1
            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
            Patents

            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
            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
            Name Type Language
            ENOXACIN
            INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
            USAN   INN  
            Official Name English
            NSC-629661
            Code English
            PD 107779
            Code English
            CI-919
            Code English
            1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)
            Common Name English
            AT-2266
            Code English
            ENOXACIN [MI]
            Common Name English
            1-ETHYL-6-FLUORO-4-OXO-7-PIPERAZIN-1-YL-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID
            Systematic Name English
            ENOXACIN [VANDF]
            Common Name English
            PD-107779
            Code English
            PENETREX
            Brand Name English
            ENOXACIN [USAN]
            Common Name English
            NSC-758416
            Code English
            ENOXACIN [ORANGE BOOK]
            Common Name English
            ENOXACIN [INN]
            Common Name English
            ENOXACIN [WHO-DD]
            Common Name English
            ENOXACIN [MART.]
            Common Name English
            Classification Tree Code System Code
            EU-Orphan Drug EU/3/15/1459
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            WHO-VATC QJ01MA04
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            NCI_THESAURUS C795
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            WHO-ATC J01MA04
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            Code System Code Type Description
            DRUG CENTRAL
            1013
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            MESH
            D015365
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            CAS
            74011-58-8
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            ChEMBL
            CHEMBL826
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            INN
            5351
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            FDA UNII
            325OGW249P
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            NCI_THESAURUS
            C65512
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            WIKIPEDIA
            ENOXACIN
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            DRUG BANK
            DB00467
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            LACTMED
            Enoxacin
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            IUPHAR
            1157
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            PUBCHEM
            3229
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            RXCUI
            3925
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY RxNorm
            EVMPD
            SUB06540MIG
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            IUPHAR
            316
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            EPA CompTox
            74011-58-8
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY
            MERCK INDEX
            M4911
            Created by admin on Fri Jun 25 21:51:50 UTC 2021 , Edited by admin on Fri Jun 25 21:51:50 UTC 2021
            PRIMARY Merck Index