Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H20FN3O3 |
| Molecular Weight | 333.3574 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCN(C)CC3
InChI
InChIKey=FHFYDNQZQSQIAI-UHFFFAOYSA-N
InChI=1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)
Pefloxacin is a fluorinated quinolone that is structurally related to nalidixic acid. It can be administered both orally and intravenously, and has a broad spectrum of in vitro activity against Gram-negative organisms and staphylococci. The bactericidal action of pefloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited. It is prescribed for the treatment of uncomplicated gonococcal urethritis in males and for gram-negative bacterial infections in gastrointestinal system and genitourinary tract.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Non-nephrotoxic empiric antimicrobial therapy in febrile neutropenic cancer patients. | 1992 |
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| [Neurologic side effects of fluoroquinolones. Apropos of 9 cases concerning pefloxacin]. | 1992 Sep-Oct |
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| The 2-pyridone antibacterial agents: 8-position modifications. | 1999 Jul |
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| Purification and inhibition by quinolones of DNA gyrases from Mycobacterium avium, Mycobacterium smegmatis and Mycobacterium fortuitum bv. peregrinum. | 1999 Sep |
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| Pefloxacin in steroid dependent and resistant idiopathic nephrotic syndrome. | 2000 Jul-Aug |
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| Evidence of different profiles of side effects and drug-drug interactions among the quinolones--the pharmacokinetic standpoint. | 2001 |
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| [An experimental study on the release of endotoxin from gram negative bacteria induced by antibiotics]. | 2001 Apr |
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| Pefloxacin and ciprofloxacin increase UVA-induced edema and immune suppression. | 2001 Aug |
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| [Tendinopathy associated with fluoroquinolones: individuals at risk, incriminated physiopathologic mechanisms, therapeutic management]. | 2001 Dec |
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| Quinolones and false-positive urine screening for opiates by immunoassay technology. | 2001 Dec 26 |
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| [Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001 Feb |
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| Studies on the significance of positive bacterial semen cultures in male fertility in Nigeria. | 2001 Jul-Aug |
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| Tendon disorders attributed to fluoroquinolones: a study on 42 spontaneous reports in the period 1988 to 1998. | 2001 Jun |
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| Pharmacokinetics of pefloxacin and its interaction with cyclosporin A, a P-glycoprotein modulator, in rat blood, brain and bile, using simultaneous microdialysis. | 2001 Mar |
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| In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico. | 2001 May |
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| Selective separation and simultaneous determination of trace levels of five types of fluorinated quinolone drugs by thin-layer chromatography/fluorescence densitometry. | 2001 May-Jun |
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| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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| Pharmacokinetics of fluoroquinolones in uncompensated cirrhosis: the significance of penetration in the ascitic fluid. | 2001 Nov |
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| [The activity of four fluoroquinolones against strains of Pseudomonas aeruginosa with a different sensitivity pattern to ceftazidime and imipenem]. | 2001 Nov |
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| Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients. | 2001 Oct |
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| [Comparative study of the bacteriostatic and bactericidal activity of levofloxacin against Pasteurella strains isolated from man]. | 2001 Oct |
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| [Efficacy of some new antibiotics in treating experimental brucellosis]. | 2002 |
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| [On fluoroquinolones treatment safety in children (clinical, morphological and catamnesis data)]. | 2002 |
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| Susceptibility of Enterobacteriaceae to beta-lactam agents and fluoroquinolones: a 3-year survey in France. | 2002 Apr |
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| Spectrophotometric determination of enrofloxacin and pefloxacin through ion-pair complex formation. | 2002 Apr 1 |
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| Ciprofloxacin induces apoptosis and inhibits proliferation of human colorectal carcinoma cells. | 2002 Feb 1 |
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| Spectrophotometric determination of ciprofloxacin, enrofloxacin and pefloxacin through charge transfer complex formation. | 2002 Jan 1 |
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| [Bacteriologic examination of gallbladder contents]. | 2002 May-Jun |
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| [Diagnosis and treatment of legionella pneumonia]. | 2002 Nov |
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| Microbial isolates in open fractures seen in the accident and emergency unit of a teaching hospital in a developing country. | 2002 Oct-Dec |
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| [Formation of virulent antigen-modified mutants (Fra-, Fra-Tox-) of plague bacteria resistant to rifampicin and quinolones]. | 2003 |
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| Determination of the antibiotic drug pefloxacin in bulk form, tablets and human serum using square wave cathodic adsorptive stripping voltammetry. | 2003 Apr 10 |
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| X-ray powder diffraction patterns for certain fluoroquinolone antibiotic drugs. | 2003 Dec |
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| A microarray-based antibiotic screen identifies a regulatory role for supercoiling in the osmotic stress response of Escherichia coli. | 2003 Feb |
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| Activities of 13 quinolones by three susceptibility testing methods against a collection of Haemophilus influenzae isolates with different levels of susceptibility to ciprofloxacin: evidence for cross-resistance. | 2003 Jan |
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| Molecular epidemiology of ampicillin-resistant clinical isolates of Salmonella enterica serovar Typhimurium. | 2003 Jun |
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| [Experience in using the new drug moxifloxacin (Avelox, "Bayer", Germaniia) in urologic practice]. | 2003 May-Jun |
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| Antibiotics for preventing recurrent urinary tract infection in non-pregnant women. | 2004 |
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| Effects of acetyl salicylate and ibuprofen on fluoroquinolone MICs on Salmonella enterica serovar typhimurium in vitro. | 2004 Apr |
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| Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | 2004 Apr |
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| A three-way comparative study on the efficacy of twin sol to gel systems and marketed eye drops of pefloxacin mesylate. | 2004 Aug |
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| Extension of the isobolographic approach to interactions studies between more than two drugs: illustration with the convulsant interaction between pefloxacin, norfloxacin, and theophylline in rats. | 2004 Mar |
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| Isolation of E. coli from foam and effects of fluoroquinolones on E. coli and foam production in male Japanese quail. | 2004 Nov |
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| Models for time-varying covariates in population pharmacokinetic-pharmacodynamic analysis. | 2004 Oct |
Patents
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WHO-ATC |
J01MA03
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NCI_THESAURUS |
C795
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WHO-VATC |
QJ01MA03
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5006
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DB00487
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2H52Z9F2Q5
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274-611-8
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51081
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CHEMBL267648
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70458-92-3
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C728
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SUB09645MIG
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PEFLOXACIN
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m8442
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100000083005
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50199
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
