Norfloxacin

Identification

Summary

Norfloxacin is a broad-spectrum fluoroquinolone antibiotic with variable activity against gram-positive and gram-negative bacteria. Typically reserved for the treatment of UTIs due to accumulation in the urine.

Generic Name
Norfloxacin
DrugBank Accession Number
DB01059
Background

A synthetic fluoroquinolone (fluoroquinolones) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA gyrase.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 319.3308
Monoisotopic: 319.133219662
Chemical Formula
C16H18FN3O3
Synonyms
  • 1-Ethyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsäure
  • 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
  • 1,4-Dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
  • NFLX
  • Norfloxacin
  • Norfloxacine
  • Norfloxacino
  • Norfloxacinum
External IDs
  • MK-366

Pharmacology

Indication

For the treatment of urinary tract infection

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofCystitis••••••••••••
Treatment ofGonococcal cervicitis••••••••••••
Treatment ofInfectious diarrhea••• •••••
Treatment ofPyelitis••••••••••••
Treatment ofPyelonephritis••••••••••••
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Norfloxacin is a quinolone/fluoroquinolone antibiotic. Norfloxacin 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. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian.

Mechanism of action

The bactericidal action of Norfloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination. Norfloxacin is a broad-spectrum antibiotic agent that is shown to be effective against various Gram-positive and Gram-negative bacterial species. The fluorine atom at the 6 position increases potency against gram-negative organisms, and the piperazine moiety at the 7 position is responsible for anti-pseudomonal activity

TargetActionsOrganism
ADNA gyrase subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA topoisomerase 4 subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
UDNA topoisomerase 2-alpha
inhibitor
Humans
UDNA gyrase subunit A
inhibitor
Staphylococcus aureus
UDNA topoisomerase 2
inhibitor
Humans
UDNA topoisomerase 4 subunit A
inhibitor
Staphylococcus aureus
Absorption

Rapid

Volume of distribution

Not Available

Protein binding

10 and 15% (Serum protein binding)

Metabolism

Via liver and kidney

Route of elimination

Norfloxacin is eliminated through metabolism, biliary excretion, and renal excretion. It is expected to undergo both glomerular filtration and tubular secretion during renal excretion, as shown by its high renal clearance rate of approximately 275 mL/min.

Half-life

3-4 hours

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Norfloxacin.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Norfloxacin.
AcemetacinAcemetacin may increase the neuroexcitatory activities of Norfloxacin.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Norfloxacin.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Norfloxacin.
Food Interactions
  • Drink plenty of fluids.
  • Limit caffeine intake.
  • Take on an empty stomach.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
Chibroxin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Co NorfloxacinTablet400 mgOralCobalt Laboratories2006-07-182018-05-18Canada flag
NorfloxacinTablet400 mgOralPharmel IncNot applicableNot applicableCanada flag
NorfloxacinTablet400 mgOralAa Pharma Inc1998-07-20Not applicableCanada flag
NorfloxacinTablet400 mgOralCobalt LaboratoriesNot applicableNot applicableCanada flag
Norfloxacine-400Tablet400 mg / tabOralPro Doc Limitee1999-08-232010-07-13Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ava-norfloxacinTablet400 mgOralAvanstra Inc2011-11-232014-08-21Canada flag
Ntp-norfloxacinTablet400 mgOralTEVA Canada LimitedNot applicableNot applicableCanada flag
PMS-norfloxacinTablet400 mgOralPharmascience Inc2002-09-262017-09-30Canada flag
Riva-norfloxacinTablet400 mgOralLaboratoire Riva Inc2000-01-312013-07-31Canada flag
Riva-norfloxacinTablet400 mgOralLaboratoire Riva Inc2008-06-132013-07-31Canada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
เอ็น-ฟล๊อกซ่า 100Tablet, coated100 mgOralบริษัท ซีฟาม จำกัด จำกัด1999-02-08Not applicableThailand flag

Categories

ATC Codes
J01RA14 — Norfloxacin and metronidazoleJ01RA13 — Norfloxacin and tinidazoleS01AE02 — NorfloxacinJ01MA06 — Norfloxacin
Drug Categories
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
Fluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Benzenoids / Aryl fluorides
show 12 more
Substituents
1,4-diazinane / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, quinolone antibiotic, fluoroquinolone antibiotic, quinolone, quinolinemonocarboxylic acid (CHEBI:100246) / Fluoroquinolones (C06687)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
N0F8P22L1P
CAS number
70458-96-7
InChI Key
OGJPXUAPXNRGGI-UHFFFAOYSA-N
InChI
InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
IUPAC Name
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCNCC1

References

Synthesis Reference
US4146719
General References
  1. Goldstein EJ: Norfloxacin, a fluoroquinolone antibacterial agent. Classification, mechanism of action, and in vitro activity. Am J Med. 1987 Jun 26;82(6B):3-17. [Article]
Human Metabolome Database
HMDB0015192
KEGG Drug
D00210
KEGG Compound
C06687
PubChem Compound
4539
PubChem Substance
46508634
ChemSpider
4380
BindingDB
50045000
RxNav
7517
ChEBI
100246
ChEMBL
CHEMBL9
ZINC
ZINC000000003742
Therapeutic Targets Database
DAP000654
PharmGKB
PA450654
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Norfloxacin
FDA label
Download (599 KB)
MSDS
Download (42.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionAdverse Reaction to Other Drugs and Medicines1
4CompletedPreventionCirrhosis of the Liver / Hepato-Renal Syndrome / Spontaneous Bacterial Peritonitis (SBP)1
4TerminatedTreatmentUrinary Tract Infection1
4Unknown StatusTreatmentUrinary Tract Infection1
3Active Not RecruitingPreventionSpontaneous Bacterial Peritonitis (SBP)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amerisource Health Services Corp.
  • Merck & Co.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Shire Inc.
Dosage Forms
FormRouteStrength
CapsuleOral
Tablet, film coatedOral
TabletOral
SolutionOral
OintmentConjunctival; Ophthalmic0.3 g
SolutionConjunctival; Ophthalmic0.3 g
SolutionConjunctival; Ophthalmic3 mg
SuspensionOral
TabletOral420.001 mg
TabletOral400 mg / tab
TabletOral408 mg
Tablet, coatedOral40000000 mg
SolutionOphthalmic3 mg / mL
Tablet, film coatedOral400 mg/1
TabletOral400.000 mg
Tablet, coatedOral
TabletOral
Capsule, coatedOral400 mg
Solution / dropsOphthalmic
Tablet, coatedOral400 mg
CapsuleOral400 mg
Tablet, film coatedOral200 mg
CapsuleOral200 mg
Tablet, film coatedOral400 mg
Tablet, coatedOral200 mg
Tablet, coatedOral100 mg
TabletOral400 mg
TabletOral200 mg
CapsuleOral100 mg
TabletOral100 mg
Tablet, film coatedOral100 mg
Prices
Unit descriptionCostUnit
Noroxin 400 mg tablet4.21USD tablet
Apo-Norflox 400 mg Tablet1.44USD tablet
Co Norfloxacin 400 mg Tablet1.28USD tablet
Novo-Norfloxacin 400 mg Tablet1.28USD tablet
Pms-Norfloxacin 400 mg Tablet1.28USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)227-228 °CPhysProp
water solubility1.78E+005 mg/LNot Available
logP-1.03HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.01 mg/mLALOGPS
logP-0.47ALOGPS
logP-0.97Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)5.58Chemaxon
pKa (Strongest Basic)8.77Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area72.88 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity85.48 m3·mol-1Chemaxon
Polarizability32.26 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9916
Blood Brain Barrier-0.9824
Caco-2 permeable-0.8683
P-glycoprotein substrateSubstrate0.8554
P-glycoprotein inhibitor INon-inhibitor0.849
P-glycoprotein inhibitor IINon-inhibitor0.8657
Renal organic cation transporterNon-inhibitor0.7588
CYP450 2C9 substrateNon-substrate0.8301
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9268
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9148
CYP450 3A4 inhibitorNon-inhibitor0.8988
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5702
Ames testAMES toxic0.9108
CarcinogenicityNon-carcinogens0.7923
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8785 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7034
hERG inhibition (predictor II)Non-inhibitor0.5292
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ufu-1092000000-bf3fd3d7faa91b8515de
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03di-0910000000-71f0a353a8e37a26b402
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0019000000-209bfb114ccbb6d9e304
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0069000000-4d54becdaa4caedbe3b2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0391000000-a84cfa736c2dcec4d545
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ufr-0069000000-246d2ae5a6ec6a55d6b1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-f809266e62551b06d730
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fmi-0039000000-b7128cd18b98a04daf9e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0069000000-d5c4d2c4b68d5f6d03a2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ue9-0095000000-901dbfc8f7d02a135c4d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0491000000-be9683c47fbf7a3cb0ba
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0970000000-90dc103f49990c57d26f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0009000000-13d5054c01078e14d8f0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fmi-0039000000-74150f6e5c4d2dcba6ab
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0059000000-dd2ee816e5228385835d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0f89-0195000000-596094ef32a4ddd39544
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0491000000-20c74694b378fdb752b2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0970000000-06c84236dac00c44e42e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ufr-0069000000-5c4650a9bab59ded6701
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0910000000-71f0a353a8e37a26b402
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-1398000000-86efb47466226acbabf9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0009000000-beda03493840aef23316
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uxr-0093000000-bd5b95da480c46f9c98e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0019000000-019b7fe9660b0864cb8f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-f75eb05432679060d266
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fia-0093000000-abbdd5070378b38ffda0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fkc-0090000000-d7c38bfceade6663c2bf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0009000000-beda03493840aef23316
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uxr-0093000000-bd5b95da480c46f9c98e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0019000000-019b7fe9660b0864cb8f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-f75eb05432679060d266
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fia-0093000000-abbdd5070378b38ffda0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fkc-0090000000-d7c38bfceade6663c2bf
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-186.7078468
predicted
DarkChem Lite v0.1.0
[M-H]-167.04971
predicted
DeepCCS 1.0 (2019)
[M-H]-186.7078468
predicted
DarkChem Lite v0.1.0
[M-H]-167.04971
predicted
DeepCCS 1.0 (2019)
[M+H]+187.2273468
predicted
DarkChem Lite v0.1.0
[M+H]+169.4077
predicted
DeepCCS 1.0 (2019)
[M+H]+187.2273468
predicted
DarkChem Lite v0.1.0
[M+H]+169.4077
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.5449468
predicted
DarkChem Lite v0.1.0
[M+Na]+176.37462
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.5449468
predicted
DarkChem Lite v0.1.0
[M+Na]+176.37462
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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]
  4. Hooper DC: Quinolone mode of action--new aspects. Drugs. 1993;45 Suppl 3:8-14. [Article]
  5. 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]
  6. 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
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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
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
P20831
Uniprot Name
DNA gyrase subunit A
Molecular Weight
99620.34 Da
References
  1. Pachanon R, Koide K, Kongsoi S, Nakajima C, Kapalamula TF, Suthienkul O, Suzuki Y: Interaction of the plasmid-encoded quinolone resistance protein QnrB19 with Salmonella Typhimurium DNA gyrase. J Infect Chemother. 2020 Nov;26(11):1139-1145. doi: 10.1016/j.jiac.2020.06.002. Epub 2020 Jul 12. [Article]
Kind
Protein group
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...

Components:
References
  1. Alkorta I, Park C, Kong J, Garbisu C, Alberti M, Pon N, Hearst JE: Rhodobacter capsulatus DNA topoisomerase I purification and characterization. Arch Biochem Biophys. 1999 Feb 1;362(1):123-30. doi: 10.1006/abbi.1998.1023. [Article]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
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
P0C1U9
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
91040.465 Da
References
  1. Fournier B, Zhao X, Lu T, Drlica K, Hooper DC: Selective targeting of topoisomerase IV and DNA gyrase in Staphylococcus aureus: different patterns of quinolone-induced inhibition of DNA synthesis. Antimicrob Agents Chemother. 2000 Aug;44(8):2160-5. doi: 10.1128/AAC.44.8.2160-2165.2000. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
This drug is a fluoroquinolone, and these agents are known to inhibit CYP1A2.
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
  1. Zhang L, Wei MJ, Zhao CY, Qi HM: Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes. Acta Pharmacol Sin. 2008 Dec;29(12):1507-14. doi: 10.1111/j.1745-7254.2008.00908.x. [Article]
  2. English BA, Dortch M, Ereshefsky L, Jhee S: Clinically significant psychotropic drug-drug interactions in the primary care setting. Curr Psychiatry Rep. 2012 Aug;14(4):376-90. doi: 10.1007/s11920-012-0284-9. [Article]
  3. Shahzadi A, Javed I, Aslam B, Muhammad F, Asi MR, Ashraf MY, Zia-ur-Rahman: Therapeutic effects of ciprofloxacin on the pharmacokinetics of carbamazepine in healthy adult male volunteers. Pak J Pharm Sci. 2011 Jan;24(1):63-8. [Article]
  4. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d 24-hydroxylase activity
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
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. McLellan RA, Drobitch RK, Monshouwer M, Renton KW: Fluoroquinolone antibiotics inhibit cytochrome P450-mediated microsomal drug metabolism in rat and human. Drug Metab Dispos. 1996 Oct;24(10):1134-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
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 performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. McLellan RA, Drobitch RK, Monshouwer M, Renton KW: Fluoroquinolone antibiotics inhibit cytochrome P450-mediated microsomal drug metabolism in rat and human. Drug Metab Dispos. 1996 Oct;24(10):1134-8. [Article]
  2. Liang X, Wang L, Ou R, Nie X, Yang Y, Wang F, Li K: Effects of norfloxacin on hepatic genes expression of P450 isoforms (CYP1A and CYP3A), GST and P-glycoprotein (P-gp) in Swordtail fish (Xiphophorus Helleri). Ecotoxicology. 2015 Oct;24(7-8):1566-73. doi: 10.1007/s10646-015-1457-1. Epub 2015 Apr 19. [Article]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Oxygen binding
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
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Liang X, Wang L, Ou R, Nie X, Yang Y, Wang F, Li K: Effects of norfloxacin on hepatic genes expression of P450 isoforms (CYP1A and CYP3A), GST and P-glycoprotein (P-gp) in Swordtail fish (Xiphophorus Helleri). Ecotoxicology. 2015 Oct;24(7-8):1566-73. doi: 10.1007/s10646-015-1457-1. Epub 2015 Apr 19. [Article]
  2. McLellan RA, Drobitch RK, Monshouwer M, Renton KW: Fluoroquinolone antibiotics inhibit cytochrome P450-mediated microsomal drug metabolism in rat and human. Drug Metab Dispos. 1996 Oct;24(10):1134-8. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48