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Identification
NameOfloxacin
Accession NumberDB01165  (APRD00502)
TypeSmall Molecule
GroupsApproved
Description

A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. [PubChem]

Structure
Thumb
Synonyms
8-Fluoro-3-methyl-9-(4-methyl-piperazin-1-yl)-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid
Ofloxacine
Ofloxacino
Ofloxacinum
OFLX
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Floxin I.V. Liq 20mg/mlliquid20 mgintravenousOrtho Pharmaceutical, Division Of Janssen Ortho Inc.Not applicableNot applicableCanada
Floxin Tablets 200mgtablet200 mgoralJanssen Inc1992-12-312002-07-31Canada
Floxin Tablets 300mgtablet300 mgoralJanssen Inc1990-12-312006-12-21Canada
Floxin Tablets 400mgtablet400 mgoralJanssen Inc1990-12-312007-01-10Canada
Novo-ofloxacintablet400 mgoralNovopharm Limited2004-06-112012-05-08Canada
Novo-ofloxacintablet300 mgoralNovopharm Limited2004-06-112012-05-08Canada
Novo-ofloxacintablet200 mgoralNovopharm Limited2004-06-112012-05-08Canada
Ocufloxsolution/ drops3 mg/mLophthalmicAllergan, Inc.1993-08-01Not applicableUs
Ocufloxsolution0.3 %ophthalmicAllergan Inc1995-12-31Not applicableCanada
Ofloxacin Tabletstablet400 mgoralAa Pharma Inc1998-02-17Not applicableCanada
Ofloxacin Tabletstablet300 mgoralAa Pharma Inc1998-02-04Not applicableCanada
Ofloxacin Tabletstablet200 mgoralAa Pharma Inc1998-02-04Not applicableCanada
PMS-ofloxacinsolution0.3 %ophthalmicPharmascience Inc2004-05-20Not applicableCanada
Sandoz Ofloxacinsolution0.3 %ophthalmicSandoz Canada Incorporated2012-07-24Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ofloxacinsolution0.3 %ophthalmicApotex Inc2004-01-22Not applicableCanada
Ofloxacintablet, film coated400 mg/1oralPd Rx Pharmaceuticals, Inc.2004-01-28Not applicableUs
Ofloxacintablet, coated200 mg/1oralDr. Reddy's Laboratories Limited2006-02-10Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicREMEDYREPACK INC.2016-03-02Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Proficient Rx LP2008-03-17Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicREMEDYREPACK INC.2016-04-11Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicHenry Schein Inc.2015-05-13Not applicableUs
Ofloxacintablet, coated400 mg/1oralDr. Reddy's Laboratories Limited2006-02-10Not applicableUs
Ofloxacinsolution/ drops3 mg/mLauricular (otic)Hi Tech Pharmacal Co., Inc.2008-03-17Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicRebel Distributors Corp2004-05-14Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicREMEDYREPACK INC.2013-07-01Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicKeltman Pharmaceuticals Inc.2010-01-15Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Rebel Distributors Corp2008-03-17Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)DIRECT RX2014-01-01Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicPhysicians Total Care, Inc.2010-04-20Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicPreferred Pharmaceuticals Inc.2016-02-15Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicAkorn, Inc.2008-07-01Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicClinical Solutions Wholesale2004-05-14Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicREMEDYREPACK INC.2013-11-252016-04-05Us
Ofloxacintablet, film coated400 mg/1oralLarken Laboratories, Inc.2014-05-20Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Pharma Force, Inc.2010-01-21Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicDIRECT RX2014-01-01Not applicableUs
Ofloxacinsolution/ drops3 mg/mLauricular (otic)Physicians Total Care, Inc.2009-05-21Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Lake Erie Medical DBA Quality Care Products LLC2008-03-17Not applicableUs
Ofloxacinsolution/ drops3 mg/mLauricular (otic)STAT Rx USA LLC2008-03-17Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Clinical Solutions Wholesale2008-03-17Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)REMEDYREPACK INC.2013-06-13Not applicableUs
Ofloxacintablet, film coated400 mg/1oralCadila Pharmaceuticals Limited2014-09-24Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Aidarex Pharmaceuticals LLC2008-03-17Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicH.J. Harkins Company, Inc.2010-01-04Not applicableUs
Ofloxacintablet, film coated300 mg/1oralCadila Pharmaceuticals Limited2014-09-24Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicSTAT RX LLC USA2004-05-14Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Lake Erie Medical DBA Quality Care Products LLC2008-03-31Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicREMEDYREPACK INC.2013-06-13Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicBausch & Lomb Incorporated2004-05-14Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Falcon Pharmaceuticals, Ltd.2008-03-31Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicREMEDYREPACK INC.2014-02-26Not applicableUs
Ofloxacintablet, film coated200 mg/1oralCadila Pharmaceuticals Limited2014-09-24Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicMwi2015-03-27Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicLake Erie Medical DBA Quality Care Products LLC2008-07-01Not applicableUs
Ofloxacintablet, film coated200 mg/1oralREMEDYREPACK INC.2013-03-27Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicPreferred Pharmaceuticals, Inc.2013-05-14Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)Bausch & Lomb Incorporated2008-03-17Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicFalcon Pharmaceuticals, Ltd.2004-05-14Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicREMEDYREPACK INC.2014-05-14Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicHi Tech Pharmacal Co., Inc.2004-05-14Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicProficient Rx LP2004-05-14Not applicableUs
Ofloxacintablet, coated300 mg/1oralDr. Reddy's Laboratories Limited2006-02-10Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicProficient Rx LP2008-07-01Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicRising Pharmaceuticals, Inc.2014-12-15Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicAmerican Regent, Inc.2010-07-01Not applicableUs
Ofloxacinsolution3 mg/mLophthalmicFdc Limited2014-12-15Not applicableUs
Ofloxacinsolution/ drops3 mg/mLophthalmicUnit Dose Services2004-05-14Not applicableUs
Ofloxacinsolution/ drops3 mg/mLauricular (otic)Rebel Distributors Corp2008-03-17Not applicableUs
Ofloxacinsolution3 mg/mLauricular (otic)REMEDYREPACK INC.2013-10-04Not applicableUs
Ofloxacinsolution/ drops3 mg/mLauricular (otic)Preferred Pharmaceuticals, Inc.2013-03-22Not applicableUs
Ofloxacin Ophthalmicsolution3 mg/mLophthalmicAltaire Pharmaceuticals Inc.2013-05-31Not applicableUs
Ofloxacin Oticsolution3 mg/mLauricular (otic)Proficient Rx LP2004-05-14Not applicableUs
Ofloxacin Oticsolution3 mg/mLauricular (otic)REMEDYREPACK INC.2014-09-30Not applicableUs
Ofloxacin Oticsolution3 mg/mLauricular (otic)Preferred Pharmaceuticals, Inc.2014-02-21Not applicableUs
Ofloxacin Oticsolution3 mg/mLauricular (otic)Apotex Corp.2004-05-14Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
FloxinNot Available
FloxstatNot Available
ZanocinNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIA4P49JAZ9H
CAS number82419-36-1
WeightAverage: 361.3675
Monoisotopic: 361.143784348
Chemical FormulaC18H20FN3O4
InChI KeyInChIKey=GSDSWSVVBLHKDQ-UHFFFAOYSA-N
InChI
InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)
IUPAC Name
7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0⁵,¹³]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
SMILES
CC1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-3-carboxylic acid
  • N-arylpiperazine
  • Fluoroquinolone
  • Hydroxyquinoline
  • Dihydroquinolone
  • Aminoquinoline
  • Dihydroquinoline
  • Benzoxazine
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Dialkylarylamine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Fluorobenzene
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of infections (respiratory tract, kidney, skin, soft tissue, UTI), urethral and cervical gonorrhoea.
PharmacodynamicsOfloxacin is a quinolone/fluoroquinolone antibiotic. Ofloxacin 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. Ofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.
Mechanism of actionOfloxacin acts on DNA gyrase and toposiomerase IV, enzymes which, like human topoisomerase, prevents the excessive supercoiling of DNA during replication or transcription. By inhibiting their function, the drug thereby inhibits normal cell division.
Related Articles
AbsorptionBioavailability of ofloxacin in the tablet formulation is approximately 98%
Volume of distributionNot Available
Protein binding32%
Metabolism

Hepatic

Route of eliminationElimination is mainly by renal excretion. Between 65% and 80% of an administered oral dose of ofloxacin is excreted unchanged via the kidneys within 48 hours of dosing. Four to eight percent of an ofloxacin dose is excreted in the feces. This indicates a small degree of biliary excretion of ofloxacin.
Half life9 hours
ClearanceNot Available
ToxicityLD50=5450 mg/kg (orally in mice)
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9545
Blood Brain Barrier-0.9659
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.7489
CYP450 2C9 substrateNon-substrate0.8468
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6386
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9268
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7726
Ames testAMES toxic0.7844
CarcinogenicityNon-carcinogens0.9033
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.1639 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8402
hERG inhibition (predictor II)Non-inhibitor0.866
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Liquidintravenous20 mg
Solutionophthalmic0.3 %
Solutionauricular (otic)3 mg/mL
Solutionophthalmic3 mg/mL
Solution/ dropsauricular (otic)3 mg/mL
Solution/ dropsophthalmic3 mg/mL
Tablet, coatedoral200 mg/1
Tablet, coatedoral300 mg/1
Tablet, coatedoral400 mg/1
Tablet, film coatedoral200 mg/1
Tablet, film coatedoral300 mg/1
Tablet, film coatedoral400 mg/1
Tabletoral200 mg
Tabletoral300 mg
Tabletoral400 mg
Prices
Unit descriptionCostUnit
Floxin Otic 0.3% Solution 10ml Bottle142.91USD bottle
Ofloxacin 10ml Otic (ear) Solution132.19USD bottle
Ofloxacin 10ml. Ophthalmic (eye) Solution87.6USD bottle
Floxin Otic 0.3% Solution 5ml Bottle86.49USD bottle
Ofloxacin 5ml Otic (ear) Solution77.21USD bottle
Ofloxacin 5ml. Ophthalmic (eye) Solution43.86USD bottle
Ocuflox 0.3% eye drops11.35USD ml
Floxin 400 mg tablet9.55USD tablet
Ofloxacin 0.3% eye drops8.08USD ml
Floxin 200 mg tablet6.6USD tablet
Ofloxacin 400 mg tablet6.12USD tablet
Ofloxacin 300 mg tablet5.81USD tablet
Floxin 300 mg tablet5.61USD tablet
Ofloxacin 200 mg tablet4.88USD tablet
Floxin otic singles4.28USD each
Ocuflox 0.3 % Solution2.75USD ml
Apo-Ofloxacin 0.3 % Solution1.04USD ml
Pms-Ofloxacin 0.3 % Solution1.04USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5401741 No1995-03-272012-03-27Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point254 dec °CPhysProp
water solubility28.3 mg/mLNot Available
logP-0.39HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP-0.02ALOGPS
logP0.65ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.45ChemAxon
pKa (Strongest Basic)6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area73.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.94 m3·mol-1ChemAxon
Polarizability36.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US4382892
General ReferencesNot Available
External Links
ATC CodesJ01MA01J01RA09S01AE01S02AA16
AHFS Codes
  • 08:12.18
  • 52:04.04
PDB EntriesNot Available
FDA labelDownload (198 KB)
MSDSDownload (73.9 KB)
Interactions
Drug Interactions
Drug
AgomelatineThe serum concentration of Agomelatine can be increased when it is combined with Ofloxacin.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Ofloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.
BendamustineThe serum concentration of Bendamustine can be increased when it is combined with Ofloxacin.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Ofloxacin.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Ofloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.
CitalopramOfloxacin may increase the QTc-prolonging activities of Citalopram.
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Ofloxacin.
DicoumarolOfloxacin may increase the anticoagulant activities of Dicoumarol.
DidanosineThe serum concentration of Didanosine can be decreased when it is combined with Ofloxacin.
DofetilideOfloxacin may increase the QTc-prolonging activities of Dofetilide.
DuloxetineThe serum concentration of Duloxetine can be increased when it is combined with Ofloxacin.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Ofloxacin.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Ofloxacin.
GoserelinGoserelin may increase the QTc-prolonging activities of Ofloxacin.
InfliximabInfliximab may increase the neuroexcitatory activities of Ofloxacin.
Insulin HumanOfloxacin may increase the hypoglycemic activities of Insulin Regular.
Iron DextranThe serum concentration of Ofloxacin can be decreased when it is combined with Iron Dextran.
IvabradineIvabradine may increase the QTc-prolonging activities of Ofloxacin.
LanthanumThe serum concentration of Ofloxacin can be decreased when it is combined with Lanthanum.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Ofloxacin.
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Ofloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium SulfateThe serum concentration of Ofloxacin can be decreased when it is combined with Magnesium Sulfate.
MifepristoneMifepristone may increase the QTc-prolonging activities of Ofloxacin.
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Ofloxacin.
OctreotideOctreotide may increase the QTc-prolonging activities of Ofloxacin.
PentoxifyllineThe serum concentration of Pentoxifylline can be increased when it is combined with Ofloxacin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Ofloxacin.
PirfenidoneThe serum concentration of Pirfenidone can be increased when it is combined with Ofloxacin.
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Ofloxacin.
PorfimerOfloxacin may increase the photosensitizing activities of Porfimer.
ProbenecidThe serum concentration of Ofloxacin can be increased when it is combined with Probenecid.
QuinaprilThe serum concentration of Ofloxacin can be decreased when it is combined with Quinapril.
RasagilineThe serum concentration of Rasagiline can be increased when it is combined with Ofloxacin.
SevelamerSevelamer can cause a decrease in the absorption of Ofloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.
Strontium ranelateThe serum concentration of Ofloxacin can be decreased when it is combined with Strontium ranelate.
SucralfateThe serum concentration of Ofloxacin can be decreased when it is combined with Sucralfate.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Ofloxacin.
TheophyllineThe metabolism of Theophylline can be decreased when combined with Ofloxacin.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Ofloxacin.
VareniclineThe serum concentration of Varenicline can be increased when it is combined with Ofloxacin.
VerteporfinOfloxacin may increase the photosensitizing activities of Verteporfin.
Food Interactions
  • Avoid high doses of caffeine.
  • Take without regard to meals.

Targets

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, including catenanes and knotted rings.
Gene Name:
gyrA
Uniprot ID:
P43700
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Schmitz FJ, Hofmann B, Hansen B, Scheuring S, Luckefahr M, Klootwijk M, Verhoef J, Fluit A, Heinz HP, Kohrer K, Jones ME: Relationship between ciprofloxacin, ofloxacin, levofloxacin, sparfloxacin and moxifloxacin (BAY 12-8039) MICs and mutations in grlA, grlB, gyrA and gyrB in 116 unrelated clinical isolates of Staphylococcus aureus. J Antimicrob Chemother. 1998 Apr;41(4):481-4. [PubMed:9598779 ]
  4. Cambau E, Sougakoff W, Besson M, Truffot-Pernot C, Grosset J, Jarlier V: Selection of a gyrA mutant of Mycobacterium tuberculosis resistant to fluoroquinolones during treatment with ofloxacin. J Infect Dis. 1994 Nov;170(5):1351. [PubMed:7963747 ]
  5. Shi R, Zhang J, Li C, Kazumi Y, Sugawara I: Emergence of ofloxacin resistance in Mycobacterium tuberculosis clinical isolates from China as determined by gyrA mutation analysis using denaturing high-pressure liquid chromatography and DNA sequencing. J Clin Microbiol. 2006 Dec;44(12):4566-8. Epub 2006 Oct 11. [PubMed:17035499 ]
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
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Turner AK, Nair S, Wain J: The acquisition of full fluoroquinolone resistance in Salmonella Typhi by accumulation of point mutations in the topoisomerase targets. J Antimicrob Chemother. 2006 Oct;58(4):733-40. Epub 2006 Aug 8. [PubMed:16895934 ]
  4. Chau TT, Campbell JI, Galindo CM, Van Minh Hoang N, Diep TS, Nga TT, Van Vinh Chau N, Tuan PQ, Page AL, Ochiai RL, Schultsz C, Wain J, Bhutta ZA, Parry CM, Bhattacharya SK, Dutta S, Agtini M, Dong B, Honghui Y, Anh DD, Canh do G, Naheed A, Albert MJ, Phetsouvanh R, Newton PN, Basnyat B, Arjyal A, La TT, Rang NN, Phuong le T, Van Be Bay P, von Seidlein L, Dougan G, Clemens JD, Vinh H, Hien TT, Chinh NT, Acosta CJ, Farrar J, Dolecek C: Antimicrobial drug resistance of Salmonella enterica serovar typhi in asia and molecular mechanism of reduced susceptibility to the fluoroquinolones. Antimicrob Agents Chemother. 2007 Dec;51(12):4315-23. Epub 2007 Oct 1. [PubMed:17908946 ]
  5. Ishiguro F, Toho M, Yamazaki M, Matsuyuki S, Moriya K, Tanaka D, Isobe J, Kyota Y, Muraoka M: [Mutations of gyrA gene and parC gene in fluoroquinolone-resistant Escherichia coli isolates from sporadic diarrheal cases]. Kansenshogaku Zasshi. 2006 Sep;80(5):507-12. [PubMed:17073264 ]
  6. Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [PubMed:9293187 ]
Kind
Protein
Organism
Human
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 segregation of daughter chromosomes. May play a role in regulating the period length of ARNTL/BMAL1 transcriptional oscillation (By similarity).
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular Weight:
174383.88 Da
References
  1. Divo AA, Sartorelli AC, Patton CL, Bia FJ: Activity of fluoroquinolone antibiotics against Plasmodium falciparum in vitro. Antimicrob Agents Chemother. 1988 Aug;32(8):1182-6. [PubMed:2847647 ]

Enzymes

Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
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 cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
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. [PubMed:10525100 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular Weight:
171589.5 Da
References
  1. Terashi K, Oka M, Soda H, Fukuda M, Kawabata S, Nakatomi K, Shiozawa K, Nakamura T, Tsukamoto K, Noguchi Y, Suenaga M, Tei C, Kohno S: Interactions of ofloxacin and erythromycin with the multidrug resistance protein (MRP) in MRP-overexpressing human leukemia cells. Antimicrob Agents Chemother. 2000 Jun;44(6):1697-700. [PubMed:10817732 ]
Kind
Protein
Organism
Human
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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. [PubMed:10411577 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
References
  1. Sasabe H, Tsuji A, Sugiyama Y: Carrier-mediated mechanism for the biliary excretion of the quinolone antibiotic grepafloxacin and its glucuronide in rats. J Pharmacol Exp Ther. 1998 Mar;284(3):1033-9. [PubMed:9495864 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular Weight:
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:25