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Enoxacin

Enoxacin Structure
CAS No.
74011-58-8
Chemical Name:
Enoxacin
Synonyms
Penetrex;1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-[1-PIPERAZINYL]-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID;ENX;ci919;enoram;Abenox;Enoxen;Enoxor;Humark;at-2266
CBNumber:
CB2403021
Molecular Formula:
C15H17FN4O3
Molecular Weight:
320.32
MOL File:
74011-58-8.mol
MSDS File:
SDS
Modify Date:
2024/11/17 16:00:36

Enoxacin Properties

Melting point 220-224 C
Boiling point 569.9±50.0 °C(Predicted)
Density 1.2931 (estimate)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
pka 6.04±0.70(Predicted)
form Solid
color Off-White to Pale Yellow
Water Solubility 50 mg/ml in 1 M NaOHSlightly soluble in sodium hydroxide, dimethyl sulfoxide, chloroform and methanol. Insoluble in water.
CAS DataBase Reference 74011-58-8(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H320-H335
Precautionary statements  P261-P280-P301+P312-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36/37
WGK Germany  2
RTECS  QN2800000
HS Code  29335995
Toxicity LD50 in male, female mice, male, female rats (mg/kg): 327, 391, 236, 294 i.v.; 1237, 1320, >2000, >2000 s.c.; all >5000 orally (Senda)

Enoxacin Chemical Properties,Uses,Production

Description

Enoxacin is a broad spectrum, quinolone-class, antibacterial agent closely related structurally to nalidixic acid. The serum half-life (6.2 hrs.) and urinary recovery (70%) are considerably greater than for other newer agents of this class, such as norfloxacin (10) and earlier mentioned ciprofloxacin.

Chemical Properties

Off-White to Pale Yellow Solid

Uses

Enoxacin is an antibacterial agent used in the treatment of gastro enteritis including infectious diarrhea, respiratory tract infections, gonorrhea and urinary tract infections. It is a bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.

Definition

ChEBI: A 1,8-naphthyridine derivative that is 1,4-dihydro-1,8-naphthyridine with an ethyl group at the 1 position, a carboxy group at the 3-position, an oxo sustituent at the 4-position, a fluoro substituent at the 5-position and a piperazin-1-yl group at the 7 p sition. An antibacterial, it is used in the treatment of urinary-tract infections and gonorrhoea.

Pharmaceutical Applications

A 1,8 naphthyridone derivative available as an oral drug. It exhibits good activity in vitro against many species of Enterobacteriaceae. It is inactive against Ps. aeruginosa, Serratia, Citrobacter, Acinetobacter and Mycobacterium spp., as well as anaerobes, chlamydiae and ureaplasmas.
It is well absorbed and widely distributed when given orally. Absorption is not significantly affected by food, but ranitidine, sucralfate and some antacids or mineral supplements may interfere with absorption. After repeated doses of 400 mg every 12 h for 14 days, mean peak plasma levels reach 3.5–4.5 mg/L, a steady state being achieved in 3–4 days.

Clinical Use

1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid (Penetrex) is a quinolone with broad-spectrum antibacterial activity that is used primarily for the treatment of urinary tract infections and sexually transmitted diseases. Enoxacin has been approved for the treatment of uncomplicated gonococcal urethritis and has also been shown to be effective in chancroid caused by Haemophilus ducreyi. A single 400-mg dose is used for these indications. Enoxacin is also approved for the treatment of acute (uncomplicated) and chronic (complicated) urinary tract infections. Enoxacin is well absorbed following oral administration. Oral bioavailability approaches 98%. Concentrations of the drug in the kidneys, prostate, cervix, fallopian tubes, and myometrium typically exceed those in the plasma. More than 50% of the unchanged drug is excreted in the urine. Metabolism, largely catalyzed by cytochrome P450 enzymes in the liver, accounts for 15% to 20% of the orally administered dose of enoxacin. The relatively short elimination half-life of enoxacin dictates twice-a-day dosing for the treatment of urinary tract infections. Some cytochrome P450 isozymes, such as CYP 1A2, are inhibited by enoxacin, resulting in potentially important interactions with other drugs. For example, enoxacin has been reported to decrease theophylline clearance, causing increased plasma levels and increased toxicity. Enoxacin forms insoluble chelates with divalent metal ions present in antacids and hematinics, which reduce its oral bioavailability.

Global( 320)Suppliers
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Enoxacin Spectrum

1,8-naphthyridine-3-carboxylicacid,1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-pi 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-car at-2266 bactidan ci919 comprecin enoram Enoxacine Gluconate Norfloxacin Enoxacin(Penetrex) Enofloxacin Enofloxacine Enoksetin NSC 629661 Enoxacin API Enoxacin solution,1000ppm Enoxacin Solution, 100ppm ENOXACIN flumark pd107779 ENX Flumeork Gyramid Enoxacin (Patent-No-Supply) Enoxacin (DMF) 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID (ENOXACIN) Abenox Enoxen Enoxor Humark 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)- Enoxacin,1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid PENETREX (enoxacin) 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)- Enoxacin USP/EP/BP 1-ethyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-yl-1,8-naphthyridine-3-carboxylate Enoxacin (AT-2266) 1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid Enoxacin 1.5-Hydrate Enoxacin (Flumark) Penetrex 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-[1-PIPERAZINYL]-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID Oleanolic Acid Impurity 9 Enoxacin in Methanol C13166950 Enoxacin 74011-58-8 C15H17FN4O3 C15H17FN4O332H2O BioChemical Antibiotics Antibiotics A-F Antibiotics A to Z Active Pharmaceutical Ingredients API's Heterocycles Intermediates & Fine Chemicals Pharmaceuticals API