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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
Structure of ENOXACIN GLUCONATE

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

HIDE SMILES / InChI

Molecular Formula C6H12O7
Molecular Weight 196.1553
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Description
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

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

6.9413759E11
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

6.9413759E11
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

6.9413759E11
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
Route: single
Dose: 600 mg
Sources:
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%)
Epidermal and dermal conditions (0.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Enoxacin acute liver injury.
1992 May
Repeated treatment with quinolones potentiates the seizures induced by aminophylline in genetically epilepsy-prone rats.
1992 Sep
Profiles of hepatic and dysrhythmic cardiovascular events following use of fluoroquinolone antibacterials: experience from large cohorts from the Drug Safety Research Unit Prescription-Event Monitoring database.
2001
Comparison of side effects of levofloxacin versus other fluoroquinolones.
2001
[Convulsion following the combination of single preoperative oral administration of enoxacine and single postoperative intravenous administration of flurbiprofen axetil].
2001 Apr
Inhibitory effect of quinolone antimicrobial and nonsteroidal anti-inflammatory drugs on a medium chain acyl-CoA synthetase.
2001 Aug 1
Polysaccharide synthesis as a carbon dissipation mechanism in metabolically uncoupled Xanthomonas campestris cells.
2001 Jul 26
Effect of liposomes and niosomes on skin permeation of enoxacin.
2001 May 21
Selective separation and simultaneous determination of trace levels of five types of fluorinated quinolone drugs by thin-layer chromatography/fluorescence densitometry.
2001 May-Jun
Multiresidue determination of (fluoro)quinolone antibiotics in swine kidney using liquid chromatography-tandem mass spectrometry.
2002 Apr 5
Spectrophotometric determination of enoxacin as ion-pairs with bromophenol blue and bromocresol purple in bulk and pharmaceutical dosage form.
2002 Jul 1
The expanding role of fluoroquinolones.
2002 Jul 8
Possible gatifloxacin-induced fulminant hepatic failure.
2002 Jul-Aug
[Phototoxicity studies of pazufloxacin mesilate, a novel parenteral quinolone antimicrobial agent--in vitro and in vivo studies].
2002 Jun
Osteoadsorptive bisphosphonate derivatives of fluoroquinolone antibacterials.
2002 May 23
In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation.
2002 May 27
Laser flash photolysis study of photoionization in fluoroquinolones.
2002 Nov
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
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
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
2004 Apr
Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin.
2004 Dec
Sensitivity and spectrum of bacterial isolates in infectious otitis externa.
2004 Mar
[Simultaneous determination of quinolones in foods by LC/MS/MS].
2004 Oct
Determination of fluoroquinolones in edible animal tissue samples by high performance liquid chromatography after solid phase extraction.
2005 Apr
HPLC determination of enoxacin, ciprofloxacin, norfloxacin and ofloxacin with photoinduced fluorimetric (PIF) detection and multiemission scanning: application to urine and serum.
2005 Aug 5
Validation of a novel HPLC sorbent material for the determination of ten quinolones in human and veterinary pharmaceutical formulations.
2005 Dec
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
Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation.
2005 Jul 4
Induced and photoinduced DNA damage by quinolones: ciprofloxacin, ofloxacin and nalidixic acid determined by comet assay.
2005 Jul-Aug
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
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
[Determination of enoxacin in urine by synchronous fluorimetry].
2005 Oct
Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101.
2006 Apr
Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA).
2006 Apr 19
Radiation-induced in vitro phototoxic potential of some fluoroquinolones.
2006 Jan
Effects of Transcutol P on the corneal permeability of drugs and evaluation of its ocular irritation of rabbit eyes.
2006 Jan
[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
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 13:39:08 UTC 2023
Edited
by admin
on Sat Dec 16 13:39:08 UTC 2023
Record UNII
FK8O5WLR9H
Record Status Validated (UNII)
Record Version
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Name Type Language
ENOXACIN GLUCONATE
Common Name English
D-GLUCONIC ACID, COMPD. WITH 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID (1:?)
Systematic Name English
Enoxacin gluconate [WHO-DD]
Common Name English
ENOXACIN GLYCONATE
Common Name English
D-GLUCONIC ACID, COMPD. WITH 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID
Systematic Name English
D-GLUCONIC ACID, COMPD. WITH 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
FK8O5WLR9H
Created by admin on Sat Dec 16 13:39:08 UTC 2023 , Edited by admin on Sat Dec 16 13:39:08 UTC 2023
PRIMARY
PUBCHEM
70480544
Created by admin on Sat Dec 16 13:39:08 UTC 2023 , Edited by admin on Sat Dec 16 13:39:08 UTC 2023
PRIMARY
CAS
85200-30-2
Created by admin on Sat Dec 16 13:39:08 UTC 2023 , Edited by admin on Sat Dec 16 13:39:08 UTC 2023
PRIMARY
CAS
104142-71-4
Created by admin on Sat Dec 16 13:39:08 UTC 2023 , Edited by admin on Sat Dec 16 13:39:08 UTC 2023
NON-SPECIFIC STOICHIOMETRY
SMS_ID
100000176176
Created by admin on Sat Dec 16 13:39:08 UTC 2023 , Edited by admin on Sat Dec 16 13:39:08 UTC 2023
PRIMARY
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