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Enoxacin

Enoxacin structure

CAS No:
74011-58-8
Formula:
C15H17FN4O3
Chemical Name:
Enoxacin
Synonyms:
1,8-Naphthyridine-3-carboxylic acid,1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-;1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid;AT 2266;Enoxacin;Enoxacine;Flumark;Penetrex;Penetrex (pharmaceutical);Enoksetin;PD 107779;CI 919;NSC 629661;Enofloxacin;ENOXOR;Enofloxacine;1-Ethyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-yl-1,8-naphthyridine-3-carboxylate;1-Ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Categories:
Active Pharmaceutical Ingredients > Inhibitor Drugs

Description

Enoxacin is a broad-spectrum 6-fluoronaphthyridinone antibacterial agent.Target: antibacterialEnoxacin is a new quinolone carboxylic acid compound. Its activity against 740 bacterial isolates was determined. It inhibited 90% Escherichia coli, Klebsiella sp., Aeromonas sp., Enterobacter spp., Serratia spp., Proteus mirabilis, and Morganella morganii at less than or equal to 0.8 micrograms/ml [1]. Daily plasma theophylline concentrations were measured in 14 patients. The mean +/- s.d. theo

Solid

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.

Enoxacin Basic Attributes

Molecular Weight：

320.32

Exact Mass：

320.32

EC Number：

1308068-626-2

UNII：

325OGW249P

NSC Number：

758416|629661

DSSTox ID：

DTXSID5022984

ATC Code：

J - Antiinfectives for systemic use

HScode：

29335995

Characteristics

PSA：

85.8

XLogP3：

2.3

Appearance：

Solid

Density：

1.4±0.1 g/cm3

Melting Point：

220-224 °C

Boiling Point：

569.9±50.0 °C at 760 mmHg

Flash Point：

298.4±30.1 °C

Refractive Index：

1.599

Water Solubility：

H2O: 50 mg/ml in 1 M NaOHSlightly soluble in sodium hydroxide, dimethyl sulfoxide, chloroform and methanol. Insoluble in water.

Storage Conditions：

2-8°C

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)

Collision Cross Section：

168.1 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|184.7 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|170.8 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|185 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]

Safety Information

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36/37

RTECS Number：

QN2800000

Marks：

Toxicity

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.

Drug Information

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.

Pharmacology：

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.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)|Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

Absorption：

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.

Mechanism of Action：

Enoxacin exerts its bactericidal action via the inhibition of the essential bacterial enzyme DNA gyrase (DNA Topoisomerase II).

MeSH Entry Terms：

AT 2266

Enoxacin Use and Manufacturing

Uses

A flurorquinolone antibacterial used to treat urinary tract infections and gonorrhea.

Use Classification：

Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:320.32
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:3
Exact Mass:320.12846858
Monoisotopic Mass:320.12846858
Topological Polar Surface Area:85.8
Heavy Atom Count:23
Complexity:521
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ethyl propionate

Toluene

Drug Function and Efficacy

This product has a broad-spectrum antibacterial effect, especially high antibacterial activity against aerobic Gram-negative bacilli. It has good antibacterial activity in vitro against the following bacteria: most bacteria of the Enterobacteriaceae family, including Citrobacter, Enterobacter cloacae, Enterobacter aerogenes, Escherichia coli, Klebsiella, Proteus, Salmonella, Shigella, Vibrio, Yersinia, etc. It often has antibacterial activity against multi-drug resistant bacteria. It has high antibacterial activity against penicillin-resistant Neisseria gonorrhoeae, enzyme-producing Haemophilus influenzae and Moraxella. It has antibacterial activity against most strains of Pseudomonas such as Pseudomonas aeruginosa. This product has antibacterial activity against methicillin-sensitive Staphylococcus aureus, and only moderate antibacterial activity against Streptococcus pneumoniae, hemolytic Streptococcus and Enterococcus faecalis. It has good antimicrobial activity against Chlamydia trachomatis, Mycoplasma, Legionella, and also has antibacterial activity against Mycobacterium tuberculosis and atypical mycobacteria. The antibacterial activity against anaerobic bacteria is poor. Enoxacin is a bactericide that acts on the A subunit of bacterial DNA helicase, inhibiting DNA synthesis and replication, leading to bacterial death.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Enoxacin
Ingredients	Active ingredient: Enoxacin.
Indication	1 Urine alkalinizing agents can reduce the solubility of this product in urine, leading to crystalluria and nephrotoxicity. 2 When this product is used in combination with theophylline, competitive inhibition of the binding site of cytochrome P450 may lead to a significant reduction in the liver elimination of theophylline, a prolonged blood elimination half-life (t1/2b), an increase in blood drug concentration, and the occurrence of symptoms of theophylline poisoning, such as nausea, vomiting, tremor, restlessness, excitement, convulsions, palpitations, etc., so it should be avoided to use it together. If it cannot be avoided, the blood concentration of theophylline should be measured and the dose should be adjusted. 3 When cyclosporine is used in combination with this product, its blood concentration increases. The blood concentration of cyclosporine must be monitored and the dose adjusted. 4 When this product is used in combination with the anticoagulant warfarin, it can enhance the latter's anticoagulant effect, so the combination of the two should be avoided. If it cannot be avoided, the patient's prothrombin time should be closely monitored and the dose adjusted. 5 Probenecid can reduce the secretion of this product from the renal tubules by about 50%. When used in combination, it may cause toxicity due to the increased blood concentration of this product. 6. This product interferes with the metabolism of caffeine, which leads to a decrease in caffeine elimination, a prolonged blood elimination half-life, and may produce central nervous system toxicity, so the two should be avoided in combination. If it cannot be avoided, the patient's blood caffeine concentration should be closely monitored and the dosage adjusted. 7. When this product is used in combination with the non-steroidal anti-inflammatory drug fenbufen, convulsions occasionally occur, so it should not be used in combination with fenbufen.
Manufacturer	Wuhan Wuyao Pharmaceutical Co., Ltd.

Enoxacin Tablets
Ingredients	The main ingredient of this product is enoxacin.
Indication	1 Urine alkalinizing agents can reduce the solubility of this product in urine, leading to crystalluria and nephrotoxicity. 2 When this product is used in combination with theophylline, competitive inhibition of the binding site of cytochrome P450 may lead to a significant reduction in the liver elimination of theophylline, a prolonged blood elimination half-life (t1/2b), an increase in blood drug concentration, and the occurrence of symptoms of theophylline poisoning, such as nausea, vomiting, tremor, restlessness, excitement, convulsions, palpitations, etc., so it should be avoided to use it together. If it cannot be avoided, the blood concentration of theophylline should be measured and the dose should be adjusted. 3 When cyclosporine is used in combination with this product, its blood concentration increases. The blood concentration of cyclosporine must be monitored and the dose adjusted. 4 When this product is used in combination with the anticoagulant warfarin, it can enhance the latter's anticoagulant effect, so the combination of the two should be avoided. If it cannot be avoided, the patient's prothrombin time should be closely monitored and the dose adjusted. 5 Probenecid can reduce the secretion of this product from the renal tubules by about 50%. When used in combination, it may cause toxicity due to the increased blood concentration of this product. 6 This product interferes with the metabolism of caffeine, resulting in reduced caffeine elimination, prolonged blood elimination half-life (t1/2), and possible central nervous system toxicity, so the two should be avoided in combination. If it cannot be avoided, the patient's blood caffeine concentration should be closely monitored and the dose adjusted. 7 Antacids containing aluminum and magnesium can reduce the oral absorption of this product and should not be used together. 8 When this product is used in combination with the non-steroidal anti-inflammatory drug fenbufen, convulsions occasionally occur, so it should not be used in combination with fenbufen.
Specifications	0.1 g
Manufacturer	Zhejiang Hisun Pharmaceutical Co., Ltd.

Enoxacin Capsules
Ingredients	The main ingredient of this product is: Enoxacin. Its chemical name is: 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid sesquihydrate.
Indication	1 Urine alkalinizing agents can reduce the solubility of this product in urine, leading to crystalluria and nephrotoxicity. 2 When this product is used in combination with theophylline, competitive inhibition of the binding site of cytochrome P450 may lead to a significant reduction in the elimination of theophylline in the liver, a prolonged elimination half-life (t1/2), an increase in blood concentration, and the appearance of symptoms of theophylline poisoning, such as nausea, vomiting, tremor, restlessness, excitement, convulsions, palpitations, etc., so it should be avoided to use it in combination. If it cannot be avoided, the blood concentration of theophylline should be measured and the dose should be adjusted. 3 When cyclosporine is used in combination with this product, its blood concentration increases. The blood concentration of cyclosporine must be monitored and the dose adjusted. 4 When this product is used in combination with the anticoagulant warfarin, it can enhance the anticoagulant effect of the latter, so the combination of the two should be avoided. If it cannot be avoided, the patient's prothrombin time should be closely monitored and the dose adjusted. 5 Probenecid can reduce the secretion of this product from the renal tubules by about 50%. When used in combination, it may cause toxicity due to the increased blood concentration of this product. 6 This product interferes with the metabolism of caffeine, resulting in reduced caffeine elimination, prolonged blood elimination half-life (t1/2), and possible central nervous system toxicity, so the two should be avoided in combination. If it cannot be avoided, the patient's blood caffeine concentration should be closely monitored and the dose adjusted. 7 Antacids containing aluminum and magnesium can reduce the oral absorption of this product and should not be used together. 8 When this product is used in combination with the non-steroidal anti-inflammatory drug fenbufen, convulsions occasionally occur, so it should not be used in combination with fenbufen.
Specifications	0.1g

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Registered Holders

Chongqing Qingyang Pharmaceutical Co., Ltd.

China
Active
Zhejiang Hisun Pharmaceutical Co., Ltd.

China
Active
Wuhan Wuyao Pharmaceutical Co., Ltd.

China
Active

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