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74011-58-8 molecular structure
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1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

ChemBase ID: 350
Molecular Formular: C15H17FN4O3
Molecular Mass: 320.3188832
Monoisotopic Mass: 320.12846864
SMILES and InChIs

SMILES:
Fc1c(N2CCNCC2)nc2n(CC)cc(c(=O)c2c1)C(=O)O
Canonical SMILES:
CCn1cc(C(=O)O)c(=O)c2c1nc(N1CCNCC1)c(c2)F
InChI:
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)
InChIKey:
IDYZIJYBMGIQMJ-UHFFFAOYSA-N

Cite this record

CBID:350 http://www.chembase.cn/molecule-350.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
IUPAC Traditional name
enoxacin
Brand Name
Penetrex
Synonyms
Enoxacin
Almitil
Bactidan
Bactidron
Comprecin
Enoksetin
Enoxen
Enroxil
Enoxin
Enoxor
Enoxacin(Penetrex)
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic Acid
Enofloxacin
Enofloxacine
Flumark
NSC 629661
PD 107779
Penetrex
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Enoxacin
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-piperazinyl]-1,8-naphthyridine-3-carboxylic acid
1-乙基-6-氟-1,4-二氢-4-氧代-7-(1-哌嗪基)-1,8-萘啶-3-羧酸
依诺沙星
CAS Number
74011-58-8
MDL Number
MFCD00133308
PubChem SID
24894528
46507505
160963813
PubChem CID
3229

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 5.50139  H Acceptors
H Donor LogD (pH = 5.5) -1.20762 
LogD (pH = 7.4) -0.99097043  Log P -0.98305196 
Molar Refractivity 83.9469 cm3 Polarizability 30.31111 Å3
Polar Surface Area 85.77 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.97  LOG S -2.47 
Solubility (Water) 1.09e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
3.43 g/L expand Show data source
Sparingly soluble in Chloroform and Methanol expand Show data source
Apperance
Off-White to Pale Yellow Solid expand Show data source
Melting Point
216-218°C expand Show data source
220-224°C expand Show data source
Hydrophobicity(logP)
-1.596 expand Show data source
2.3 expand Show data source
Storage Condition
-20°C expand Show data source
2-8°C expand Show data source
Refrigerator expand Show data source
RTECS
QN2800000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... CYP1A2(1544) expand Show data source
Purity
95% expand Show data source
Grade
analytical standard expand Show data source
Salt Data
Free Basef expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02195045 external link
(1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-
[1-piperazinyl]-1,8-naphthyridine-3-carboxylic acid)
DrugBank - DB00467 external link
Item Information
Drug Groups approved
Description A broad-spectrum 6-fluoronaphthyridinone antibacterial agent (fluoroquinolones) structurally related to nalidixic acid. [PubChem]
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.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation 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.
Absorption Rapidly absorbed following oral administration, with an absolute oral bioavailability of approximately 90%.
Half Life Plasma half-life is 3 to 6 hours.
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.
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1756 external link
Research Area: Infection
Biological Activity:
Enoxacin(Penetrex) is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Insomnia is a common adverse effect. [1]
Sigma Aldrich - E3764 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
亲水性氟喹诺酮抗生素。NorA(金黄色葡萄球菌内的一种能量依赖性药外排泵)的底物。NorA 表达是造成某些耐药菌感染的原因。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E3764.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - E557600 external link
A fluororquinolone antibacterial used to treat urinary tract infections and gonorrhea.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Enoxacin
  • • Liu, A., et al.: Antimicrob. Agents Chemother., 54, 1393 (2010)
  • • Chen, P., et al.: Drug Test Anal., 2, 24 (2010)
  • • Gohil, V., et al.: Nat., Biotechnol., 28, 249 (2010)
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PATENTS

PATENTS

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INTERNET

INTERNET

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