Identification
- Summary
Pefloxacin is an antibiotic used to treat a variety of bacterial infections.
- Generic Name
- Pefloxacin
- DrugBank Accession Number
- DB00487
- Background
A synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pefloxacin (DB00487)
- Weight
- Average: 333.3574
Monoisotopic: 333.148869726 - Chemical Formula
- C17H20FN3O3
- Synonyms
- Pefloxacin
- Pefloxacine
- Pefloxacino
- Pefloxacinum
- PFLX
Pharmacology
- Indication
For the treatment of uncomplicated gonococcal urethritis in males and for gram-negative-bacterial infections in the gastrointestinal system and the genitourinary tract.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Susceptible bacterial infections •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Pefloxacin is a fluoroquinolone antibiotic. Flouroquinolones such as pefloxacin possess excellent activity against gram-negative aerobic bacteria such as E.coli and Neisseria gonorrhoea as well as gram-positive bacteria including S. pneumoniae and Staphylococcus aureus. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.
- Mechanism of action
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.
Target Actions Organism ADNA topoisomerase 4 subunit A inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) ADNA gyrase subunit A inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) UDNA topoisomerase 2-alpha inhibitorHumans UDNA topoisomerase 1 inhibitorStaphylococcus aureus - Absorption
Well absorbed by the oral route.
- Volume of distribution
Not Available
- Protein binding
20-30%
- Metabolism
Hepatic. Primary metabolites are pefloxacin N-oxide and norfloxacin.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
8.6 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Adverse reactions include peripheral neuropathy, nervousness, agitation, anxiety, and phototoxic events (rash, itching, burning) due to sunlight exposure.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Pefloxacin. Aceclofenac Aceclofenac may increase the neuroexcitatory activities of Pefloxacin. Acemetacin Acemetacin may increase the neuroexcitatory activities of Pefloxacin. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Pefloxacin. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Pefloxacin. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pefloxacin mesylate 5IAD0UV3FH 70458-95-6 HQQSBEDKMRHYME-UHFFFAOYSA-N Pefloxacin mesylate dihydrate CX28QC6FU0 149676-40-4 LEULAXMUNMRLPW-UHFFFAOYSA-N - International/Other Brands
- Labocton
Categories
- ATC Codes
- J01MA03 — Pefloxacin
- Drug Categories
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Fluoroquinolones
- Heterocyclic Compounds, Fused-Ring
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Quinolines
- Quinolones
- Topoisomerase II Inhibitors
- Topoisomerase Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Quinolines and derivatives
- Sub Class
- Quinoline carboxylic acids
- Direct Parent
- Quinoline carboxylic acids
- Alternative Parents
- N-arylpiperazines / Fluoroquinolones / Aminoquinolines and derivatives / Hydroquinolones / Haloquinolines / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / N-methylpiperazines / Aryl fluorides show 13 more
- Substituents
- 1,4-diazinane / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- N-arylpiperazine, N-alkylpiperazine, quinolone antibiotic, fluoroquinolone antibiotic, quinolone (CHEBI:50199)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 2H52Z9F2Q5
- CAS number
- 70458-92-3
- InChI Key
- FHFYDNQZQSQIAI-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
- SMILES
- CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1
References
- Synthesis Reference
- US4292317
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014630
- KEGG Drug
- D02306
- PubChem Compound
- 51081
- PubChem Substance
- 46507338
- ChemSpider
- 46291
- BindingDB
- 57936
- 7960
- ChEBI
- 50199
- ChEMBL
- CHEMBL267648
- ZINC
- ZINC000000001894
- Therapeutic Targets Database
- DAP001001
- PharmGKB
- PA164742856
- Wikipedia
- Pefloxacin
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral Injection, solution Tablet, coated Tablet, film coated Oral 400 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 271 dec °C PhysProp water solubility 11.4 mg/mL at 25 °C Not Available logP 0.27 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 1.23 mg/mL ALOGPS logP 0.2 ALOGPS logP 0.26 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 5.55 Chemaxon pKa (Strongest Basic) 7.01 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 64.09 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 90.77 m3·mol-1 Chemaxon Polarizability 34.42 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9914 Blood Brain Barrier - 0.9651 Caco-2 permeable + 0.9002 P-glycoprotein substrate Substrate 0.8136 P-glycoprotein inhibitor I Non-inhibitor 0.8781 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Non-inhibitor 0.6812 CYP450 2C9 substrate Non-substrate 0.8645 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6809 CYP450 1A2 substrate Non-inhibitor 0.9275 CYP450 2C9 inhibitor Non-inhibitor 0.9206 CYP450 2D6 inhibitor Non-inhibitor 0.9112 CYP450 2C19 inhibitor Non-inhibitor 0.8584 CYP450 3A4 inhibitor Non-inhibitor 0.9524 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6784 Ames test AMES toxic 0.9108 Carcinogenicity Non-carcinogens 0.8816 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.9255 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7983 hERG inhibition (predictor II) Non-inhibitor 0.7795
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.6490062 predictedDarkChem Lite v0.1.0 [M-H]- 174.27812 predictedDeepCCS 1.0 (2019) [M+H]+ 192.7187062 predictedDarkChem Lite v0.1.0 [M+H]+ 176.63612 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.5970062 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.68292 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dna topoisomerase type ii (atp-hydrolyzing) activity
- Specific Function
- Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
- Gene Name
- parC
- Uniprot ID
- P43702
- Uniprot Name
- DNA topoisomerase 4 subunit A
- Molecular Weight
- 83366.24 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Varon E, Houssaye S, Grondin S, Gutmann L: Nonmolecular test for detection of low-level resistance to fluoroquinolones in Streptococcus pneumoniae. Antimicrob Agents Chemother. 2006 Feb;50(2):572-9. [Article]
- Rafii F, Park M, Novak JS: Alterations in DNA gyrase and topoisomerase IV in resistant mutants of Clostridium perfringens found after in vitro treatment with fluoroquinolones. Antimicrob Agents Chemother. 2005 Feb;49(2):488-92. [Article]
- Vila J, Sanchez-Cespedes J, Sierra JM, Piqueras M, Nicolas E, Freixas J, Giralt E: Antibacterial evaluation of a collection of norfloxacin and ciprofloxacin derivatives against multiresistant bacteria. Int J Antimicrob Agents. 2006 Jul;28(1):19-24. Epub 2006 Jun 14. [Article]
- Oyamada Y, Ito H, Fujimoto K, Asada R, Niga T, Okamoto R, Inoue M, Yamagishi J: Combination of known and unknown mechanisms confers high-level resistance to fluoroquinolones in Enterococcus faecium. J Med Microbiol. 2006 Jun;55(Pt 6):729-36. [Article]
- Kind
- Protein
- Organism
- Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dna topoisomerase type ii (atp-hydrolyzing) activity
- Specific Function
- DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
- Gene Name
- gyrA
- Uniprot ID
- P43700
- Uniprot Name
- DNA gyrase subunit A
- Molecular Weight
- 97817.145 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Gootz TD, Zaniewski RP, Haskell SL, Kaczmarek FS, Maurice AE: Activities of trovafloxacin compared with those of other fluoroquinolones against purified topoisomerases and gyrA and grlA mutants of Staphylococcus aureus. Antimicrob Agents Chemother. 1999 Aug;43(8):1845-55. [Article]
- Bebear CM, Renaudin H, Charron A, Bove JM, Bebear C, Renaudin J: Alterations in topoisomerase IV and DNA gyrase in quinolone-resistant mutants of Mycoplasma hominis obtained in vitro. Antimicrob Agents Chemother. 1998 Sep;42(9):2304-11. [Article]
- Varon E, Houssaye S, Grondin S, Gutmann L: Nonmolecular test for detection of low-level resistance to fluoroquinolones in Streptococcus pneumoniae. Antimicrob Agents Chemother. 2006 Feb;50(2):572-9. [Article]
- Hombrouck C, Capmau ML, Moreau N: Overexpression, purification and photoaffinity labeling with a 3H-analogue of norfloxacin, of the GyrA and GyrB subunits of the DNA gyrase. Cell Mol Biol (Noisy-le-grand). 1999 May;45(3):347-52. [Article]
- Hooper DC: Quinolone mode of action--new aspects. Drugs. 1993;45 Suppl 3:8-14. [Article]
- Fukuda H, Hori S, Hiramatsu K: Antibacterial activity of gatifloxacin (AM-1155, CG5501, BMS-206584), a newly developed fluoroquinolone, against sequentially acquired quinolone-resistant mutants and the norA transformant of Staphylococcus aureus. Antimicrob Agents Chemother. 1998 Aug;42(8):1917-22. [Article]
- Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Ubiquitin binding
- Specific Function
- Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Magnesium ion binding
- Specific Function
- Releases the supercoiling and torsional tension of DNA, which is introduced during the DNA replication and transcription, by transiently cleaving and rejoining one strand of the DNA duplex. Introdu...
- Gene Name
- topA
- Uniprot ID
- Q06AK7
- Uniprot Name
- DNA topoisomerase 1
- Molecular Weight
- 79099.16 Da
References
- Tabary X, Moreau N, Dureuil C, Le Goffic F: Effect of DNA gyrase inhibitors pefloxacin, five other quinolones, novobiocin, and clorobiocin on Escherichia coli topoisomerase I. Antimicrob Agents Chemother. 1987 Dec;31(12):1925-8. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Fuhr U, Anders EM, Mahr G, Sorgel F, Staib AH: Inhibitory potency of quinolone antibacterial agents against cytochrome P450IA2 activity in vivo and in vitro. Antimicrob Agents Chemother. 1992 May;36(5):942-8. [Article]
- Kinzig-Schippers M, Fuhr U, Zaigler M, Dammeyer J, Rusing G, Labedzki A, Bulitta J, Sorgel F: Interaction of pefloxacin and enoxacin with the human cytochrome P450 enzyme CYP1A2. Clin Pharmacol Ther. 1999 Mar;65(3):262-74. doi: 10.1016/S0009-9236(99)70105-0. [Article]
- Labedzki A, Buters J, Jabrane W, Fuhr U: Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2. Biochem Pharmacol. 2002 Jun 15;63(12):2159-67. [Article]
- Zhou SF, Yang LP, Zhou ZW, Liu YH, Chan E: Insights into the substrate specificity, inhibitors, regulation, and polymorphisms and the clinical impact of human cytochrome P450 1A2. AAPS J. 2009 Sep;11(3):481-94. doi: 10.1208/s12248-009-9127-y. Epub 2009 Jul 10. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:31