Enoxacin

Base Information

• Chemical Name: Enoxacin
• CAS No.: 74011-58-8
• Molecular Formula: C15H17FN4O3
• Molecular Weight: 320.323
• Hs Code.: 29335995
• NSC Number: 758416,629661
• UNII: 325OGW249P
• DSSTox Substance ID: DTXSID5022984
• Nikkaji Number: J20.568K
• Wikipedia: Enoxacin
• Wikidata: Q1639616
• NCI Thesaurus Code: C65512
• Pharos Ligand ID: 42BGH2DF7K8T
• Metabolomics Workbench ID: 42815
• ChEMBL ID: CHEMBL826
• Mol file: 74011-58-8.mol

Synonyms:AT 2266;AT-2266;AT2266;CI 919;CI-919;CI919;Enoxacin;Enoxacin Sesquihydrate;Enoxin;Enoxor;PD 107779;PD-107779;PD107779;Penetrex;Sesquihydrate, Enoxacin

Chemical Property of Enoxacin

Chemical Property:

• Appearance/Colour: off-white to yellow crystals
• Melting Point: 220-224 °C
• Boiling Point: 569.9 °C at 760 mmHg
• PKA: 6.04±0.70(Predicted)
• Flash Point: 298.4 °C
• PSA: 87.46000
• Density: 1.388 g/cm³
• LogP: 1.05710
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 50 mg/ml in 1 M NaOHSlightly soluble in sodium hydroxide, dimethyl sulfoxide, chloroform and methanol. Insoluble in water.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 320.12846858
• Heavy Atom Count: 23
• Complexity: 521

Purity/Quality:

99%, ^*data from raw suppliers

Enoxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C=C(C(=O)C2=CC(=C(N=C21)N3CCNCC3)F)C(=O)O
• Recent ClinicalTrials: Enoxacin for Amyotrophic Lateral Sclerosis (ALS)
• 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. Enoxacin is a fluoroquinolone antibiotic. It is active against clinical isolates of a variety of Gram-positive and Gram-negative bacteria, including S. aureus, E. coli, K. pneumoniae, P. aeruginosa, and S. marcescens (MIC50s = 1, 0.12, 0.25, 0.5, and 1 mg/L, respectively). Enoxacin inhibits S. aureus DNA gyrase supercoiling activity and topoisomerase IV DNA decatenation (IC50s = 126 and 26.5 μg/ml, respectively). It increases survival in mouse models of systemic S. aureus, E. coli, K. pneumoniae, P. aeruginosa, and S. marcescens infection with ED50 values of 15.1, 2.2, 4.1, 120.3, and 7.6 mg/kg, respectively. Enoxacin (4 and 8 mg/kg per day) also reduces tumor growth in a 143B human osteosarcoma mouse xenograft model. Formulations containing enoxacin have previously been used in the treatment of urinary tract infections and gonorrhea.
• Uses: A fluororquinolone antibacterial used to treat urinary tract infections and gonorrhea. A flurorquinolone antibacterial used to treat urinary tract infections and gonorrhea. 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.
• Therapeutic Function: Antibacterial, Antiinfective
• 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.

Technology Process of Enoxacin

There total 25 articles about Enoxacin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

7-(4-ethoxycarbonyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (92741-52-1) → enoxacine (74011-58-8)

Guidance literature:

With sodium hydroxide; In ethanol; for 4h; Heating;

DOI:10.1002/jhet.5570210309

Reference yield: 68.0%

piperazine (110-85-0) + 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(p-tolylsulfonyl)-1,8-naphthyridine-3-carboxylic acid (114171-68-5) → enoxacine (74011-58-8)

Guidance literature:

With triethylamine; In acetonitrile; for 0.5h; Heating;

DOI:10.1002/jhet.5570240520

Reference yield:

ethyl 3-(ethylamino)propanoate (23651-62-9) → enoxacine (74011-58-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / NaHCO₃ / dimethylformamide / 8 h / 110 - 120 °C

2: 85 percent / NaH, ethanol / toluene / 2 h / Ambient temperature

3: 94 percent / chloranil / toluene / 1.5 h / Heating

4: 89 percent / 1N-NaOH / dioxane / 1 h / Heating

5: 92 percent / m-chloroperoxybenzoic acid / CHCl₃ / 1 h / Ambient temperature; excess of reagent

6: 68 percent / triethylamine / acetonitrile / 0.5 h / Heating

With sodium hydroxide; ethanol; chloranil; sodium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/jhet.5570240520

upstream raw materials:

piperazine

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(p-tolylsulfonyl)-1,8-naphthyridine-3-carboxylic acid

7-(4-ethoxycarbonyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

ethyl 3-(ethylamino)propanoate

Refernces

• 1、 Miyamoto,Egawa,Shibamori,Matsumoto. "Synthesis and reactions of 7-substituted 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acids as an antibacterial agent". . p. 1333 - 1339. Retrieved 2007/10/02.
• 2、 -. "Sesquihydrate of naphthyridine derivative, and process for the preparation thereof". . . Retrieved 2008/06/13.