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| 250mg |
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Enoxacin (also known as AT-2266, CI919, Pd107779, NSC 629661) is an orally bioavailable, broad-spectrum antibacterial agent of the fluoroquinolone class. It is used to treat a wide range of infections, including gonorrhea and urinary tract infections, by inhibiting bacterial DNA gyrase and topoisomerase IV. By binding to the DNA active site, enoxacin modifies the enzyme's breakage/reunion activity. In the absence of ATP, enoxacin promotes the cleavage of both relaxed and supercoiled forms of DNA.
| Targets |
Quinolone
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|---|---|
| ln Vitro |
Enoxacin hydrate (also known as Enoxacin sesquihydrate) improves in a dose-dependent manner, with a median effective concentration (EC50) of approximately 30 µM, siGFP-mediated gene knockdown mediated by siRNA against EGFP in HEK293 cells-based reporter system, while having no effect on the cells expressing GFP alone. In HEK293 cells, enoxacin (50 µM) facilitates siRNA duplex loading onto RISCs and miRNA processing[3].
Enoxacin has no impact on the way that Dicer alone processes pre-let-7 or pre-miR-30a. On the other hand, the combination of Enoxacin and TRBP can improve let-7 or pre-miR-30a processing[3]. Enoxacin inhibits 90% of the following microorganisms: Escherichia coli, Aeromonas sp., Enterobacter spp., Serratia spp., Proteus mirabilis, and Morganella morganii at less than or equal to 0.8 micrograms/ml[5]. |
| ln Vivo |
Enoxacin hydrate (Enoxacin sesquihydrate; 100 µM; 2 µl; injected into ear once a day for 3 consecutive days (days 12, 13 and 14)) improves the efficiency of Lv-siGFP-induced GFP mRNA knockdown (from 80% to 60%; 40% GFP mRNA level remained), while alone has no effect on GFP expression in the GFP transgenic line C57BL/6-Tg(ACTB-EGFP)1Osb/J (10 d old) using lentivirus expressing shGFP (Lv-siGFP; injected into ear for 10 days)[3].
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Rapidly absorbed following oral administration, with an absolute oral bioavailability of approximately 90%. Metabolism / Metabolites Hepatic. Some isozymes of the cytochrome P-450 hepatic microsomal enzyme system are inhibited by enoxacin. After a single dose, greater than 40% was recovered in urine by 48 hours as unchanged drug. Biological Half-Life Plasma half-life is 3 to 6 hours. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation Fluoroquinolones have traditionally not been used in infants because of concern about adverse effects on the infants' developing joints. However, recent studies indicate little risk. The calcium in milk might prevent absorption of the small amounts of fluoroquinolones in milk, but insufficient data exist to prove or disprove this assertion. Use of enoxacin is probably acceptable in nursing mothers with monitoring of the infant for possible effects on the gastrointestinal flora, such as diarrhea or candidiasis (thrush, diaper rash). However, it is preferable to use an alternate drug for which safety information is available. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. Protein Binding Enoxacin is approximately 40% bound to plasma proteins in healthy subjects and is approximately 14% bound to plasma proteins in patients with impaired renal function. |
| References |
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| Additional Infomation |
Enoxacin is 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 position. An antibacterial, it is used in the treatment of urinary-tract infections and gonorrhoea. It has a role as an antibacterial drug and a DNA synthesis inhibitor. It is a monocarboxylic acid, an amino acid, a 1,8-naphthyridine derivative, a N-arylpiperazine, a quinolone antibiotic and a fluoroquinolone antibiotic.
A broad-spectrum 6-fluoronaphthyridinone antibacterial agent (fluoroquinolones) structurally related to nalidixic acid. A broad-spectrum 6-fluoronaphthyridinone antibacterial agent that is structurally related to NALIDIXIC ACID. See also: Enoxacin Sesquihydrate (is active moiety of). Drug Indication For the treatment of adults (≥18 years of age) with the following infections caused by susceptible strains of the designated microorganisms: (1) uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae, (2) uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis, or Staphylococcus saprophyticus, and (3) complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae. Mechanism of Action Enoxacin exerts its bactericidal action via the inhibition of the essential bacterial enzyme DNA gyrase (DNA Topoisomerase II). Pharmacodynamics Enoxacin is a quinolone/fluoroquinolone antibiotic. Enoxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Enoxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. Enoxacin may be active against pathogens resistant to drugs that act by different mechanisms. |
| Molecular Formula |
C₁₅H₁₇FN₄O₃.₃/₂H₂O
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|---|---|
| Molecular Weight |
347.34
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| Exact Mass |
320.128
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| CAS # |
84294-96-2
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| Related CAS # |
84294-96-2 (Enoxacin hydrate;Enoxacin sesquihydrate; AT-2266 hydrate; CI-919 hydrate); 74011-58-8 (free)
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| PubChem CID |
3229
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| Appearance |
White to yellow solid powder
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| Melting Point |
226 °C
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| LogP |
0.992
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
23
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| Complexity |
521
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
IDYZIJYBMGIQMJ-UHFFFAOYSA-N
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| InChi Code |
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)
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| Chemical Name |
1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid
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| Synonyms |
Enoxacin sesquihydrate; AT-2266 hydrate; CI-919 hydrate; Enoxacin hydrate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
1M NaOH: ~100 mg/mL (~287.9 mM)
DMSO: ~2.78 mg/mL (~8.0 mM) H2O: ~1 mg/mL (~2.9 mM) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8790 mL | 14.3951 mL | 28.7902 mL | |
| 5 mM | 0.5758 mL | 2.8790 mL | 5.7580 mL | |
| 10 mM | 0.2879 mL | 1.4395 mL | 2.8790 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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