Ofloxacin

Identification

Summary

Ofloxacin is an antibacterial agent used for the treatment of bacterial infections in many parts of the body, including the respiratory tract, kidney, skin, soft tissue, and urinary tract.

Brand Names
Ocuflox
Generic Name
Ofloxacin
DrugBank Accession Number
DB01165
Background

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

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 361.3675
Monoisotopic: 361.143784348
Chemical Formula
C18H20FN3O4
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
  • Ofloxacin
  • Ofloxacine
  • Ofloxacino
  • Ofloxacinum
  • OFLX
External IDs
  • DL-8280
  • HOE 280
  • HOE-280

Pharmacology

Indication

For the treatment of infections (respiratory tract, kidney, skin, soft tissue, UTI), urethral and cervical gonorrhoea.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute bacterial exacerbation of chronic bronchitis••••••••••••
Treatment ofAcute otitis media••••••••••••
Treatment ofBacterial infections••••••••••••
Treatment ofCervicitis••••••••••••
Treatment ofCommunity-acquired pneumonia••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ofloxacin 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 action

Ofloxacin 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.

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
Absorption

Bioavailability of ofloxacin in the tablet formulation is approximately 98%

Volume of distribution

Not Available

Protein binding

32%

Metabolism

Hepatic

Route of elimination

Ofloxacin is mainly eliminated by renal excretion, where between 65% and 80% of an administered oral dose of ofloxacin is excreted unchanged via urine within 48 hours of dosing. About 4-8% of an ofloxacin dose is excreted in the feces and the drug is minimally subject to biliary excretion.

Half-life

9 hours

Clearance

Not Available

Adverse Effects
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Toxicity

LD50=5450 mg/kg (orally in mice)

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 Ofloxacin.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Ofloxacin.
AcemetacinAcemetacin may increase the neuroexcitatory activities of Ofloxacin.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Ofloxacin.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Ofloxacin.
Food Interactions
  • Limit caffeine intake.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ofloxacin hydrochlorideI2UWV315WA118120-51-7CAOOISJXWZMLBN-UHFFFAOYSA-N
Product Images
International/Other Brands
Floxstat / Zanocin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FloxinTablet, coated200 mg/1OralOrtho Mc Neil Pharmaceuticals1990-12-282009-01-31US flag
FloxinTablet, coated200 mg/1OralPhysicians Total Care, Inc.1993-08-032011-05-31US flag
FloxinTablet, coated400 mg/1OralOrtho Mc Neil Pharmaceuticals1990-12-282009-01-31US flag
FloxinTablet, coated400 mg/1OralPhysicians Total Care, Inc.1992-12-082011-05-31US flag
FloxinTablet, coated300 mg/1OralOrtho Mc Neil Pharmaceuticals1990-12-282009-01-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-ofloxacinSolution0.3 %OphthalmicApotex Corporation2004-01-22Not applicableCanada flag
Floxin OticSolution / drops3 mg/1mLAuricular (otic)ALMATICA PHARMA INC.2016-07-252019-11-15US flag
Novo-ofloxacinTablet200 mgOralNovopharm Limited2004-06-112012-05-08Canada flag
Novo-ofloxacinTablet400 mgOralNovopharm Limited2004-06-112012-05-08Canada flag
Novo-ofloxacinTablet300 mgOralNovopharm Limited2004-06-112012-05-08Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EXOPRED (OPHTHALMIC SUSPENSION)Ofloxacin (3 MG/1ML) + Prednisolone (10 MG/1ML)SuspensionOphthalmicบริษัท แอลเลอร์แกน (ประเทศไทย) จำกัด2016-07-14Not applicableThailand flag

Categories

ATC Codes
J01MA01 — OfloxacinJ01RA09 — Ofloxacin and ornidazoleS01AE01 — OfloxacinS02AA16 — Ofloxacin
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 / Benzoxazines / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / N-methylpiperazines
show 15 more
Substituents
1,4-diazinane / Alkyl aryl ether / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, organic heterotricyclic compound, N-alkylpiperazine, quinolone antibiotic, fluoroquinolone antibiotic, 3-oxo monocarboxylic acid, oxazinoquinoline (CHEBI:7731)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
A4P49JAZ9H
CAS number
82419-36-1
InChI Key
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[7.3.1.0^{5,13}]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

References

Synthesis Reference
US4382892
General References
Not Available
Human Metabolome Database
HMDB0015296
KEGG Drug
D00453
KEGG Compound
C07321
PubChem Compound
4583
PubChem Substance
46507574
ChemSpider
4422
BindingDB
50045004
RxNav
7623
ChEBI
7731
ChEMBL
CHEMBL4
Therapeutic Targets Database
DAP000655
PharmGKB
PA450684
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ofloxacin
FDA label
Download (198 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCorneal Transplant / Grafting, Corneal / Keratoplasty, Lamellar / Transplantation, Cornea1
4CompletedOtherInfection1
4CompletedSupportive CareAmoxicillin / Metronidazole / Ofloxacin / Periodontitis / Root Planing1
4CompletedTreatmentCataracts1
4CompletedTreatmentFever / Urinary Tract Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Akorn Inc.
  • Alcon Laboratories
  • Allergan Inc.
  • American Regent
  • Apotex Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Bausch & Lomb Inc.
  • Cipla Ltd.
  • Daiichi Sankyo
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Falcon Pharmaceuticals Ltd.
  • H.J. Harkins Co. Inc.
  • Hi Tech Pharmacal Co. Inc.
  • Innoviant Pharmacy Inc.
  • Janssen-Ortho Inc.
  • Lake Erie Medical and Surgical Supply
  • Novex Pharma
  • Nucare Pharmaceuticals Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Pacific Pharma Lp
  • Pack Pharmaceuticals
  • Par Pharmaceuticals
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmaforce Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prescript Pharmaceuticals
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Sandhills Packaging Inc.
  • Santen Inc.
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
Solution / dropsAuricular (otic)
OintmentOphthalmic0.3 %
Solution / dropsOphthalmic3 MG/ML
SuspensionOphthalmic
TabletOral
TabletOral400.00 mg
Tablet, film coatedOral200.00 MG
OintmentOphthalmic
Tablet, coatedOral200 mg/1
Tablet, coatedOral300 mg/1
Tablet, coatedOral400 mg/1
LiquidIntravenous20 mg / mL
TabletOral300 mg
TabletOral400 mg
SolutionIntravenous400 mg
Tablet, coatedOral400 mg
Solution / dropsAuricular (otic)0.3 %
Tablet, coatedOral100 mg
TabletOral400.000 mg
SolutionAuricular (otic)
Injection, solutionIntravenous200 mg/100ml
Solution / dropsOphthalmic0.3 %
SolutionOphthalmic0.3 %
SolutionOphthalmic3.000 mg
TabletOral200 mg
SolutionAuricular (otic)3 mg
InjectionIntravenous200 mg/100ml
Tablet, coatedOral
SolutionConjunctival; Ophthalmic3 mg
SolutionAuricular (otic)0.2 mg/1mL
SolutionAuricular (otic)3 mg/1mL
SolutionOphthalmic3 mg/1mL
Solution / dropsAuricular (otic)3 mg/1mL
Solution / dropsOphthalmic3 mg/1mL
TabletOral200 mg/1
TabletOral300 mg/1
TabletOral400 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral400 mg/1
Tablet, film coatedOral
Solution / dropsOphthalmic
InjectionIntravenous
SolutionOral3 mg
Tablet, film coatedOral200 mg
Injection, solutionIntravenous
Tablet, film coatedOral400 mg
SolutionAuricular (otic)
SolutionAuricular (otic)3 mg/ml
SolutionIntravenous200 mg
Tablet, coatedOral300 mg
LiquidAuricular (otic)3 mg/1ml
LiquidOphthalmic3 mg/1ml
Tablet, coatedOral200 mg
Tablet, film coatedOral100 mg
TabletOral100 mg
Solution2 mg/1ml
Capsule100 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)Region
US5401741No1995-03-282012-03-27US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)254 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
logP0.09Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.35Chemaxon
pKa (Strongest Basic)6.72Chemaxon
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-2019000000-30d77332fe9feb70a82d
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSsplash10-004i-0092000000-ce7a3d283add701efa88
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0089-0920000000-16bd425ab62950a6c1f7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-066u-4849000000-62a3272bb7a7b0465316
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-044i-4069000000-fc2f3ccfc4622b82671d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0009000000-8ca4d2a7e1305755f3d3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-02t9-0019000000-a2e5b08b64a9acd1d2f8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1093000000-8403d1bb463eb3fb6e3e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1090000000-ee50b73ec2b046ce37ca
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ck9-1490000000-8b09e639f03f4aa7a14a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0adl-1950000000-0c369c959a56510a5ff7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-02t9-0029000000-3b84ed4e6dd24267cf5d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-07r0-1590000000-4be12443c6e428a5b6b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0091000000-a74a0303807ced89f7cc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0cml-0590000000-c08e9fca2077fb0daa17
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0009000000-9046beaae10bda8773cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0009000000-97824faaceab754612c9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0159000000-de443922130ae95667e4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0089-0920000000-16bd425ab62950a6c1f7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1269000000-01b22da2e2e9a9fdbc27
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-2492000000-e0ea454a6ebaa02d7ae9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0009000000-36259e1f93e7f0591ff8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0029000000-575d0b555ec70a134ced
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-a4319ee2062d2e84d33e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0292-0059000000-d39f6e7bcbdc53f172d1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-0019000000-52f593d297a6cb46de27
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pic-0398000000-41f0181effb1e475d616
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]-195.5502641
predicted
DarkChem Lite v0.1.0
[M-H]-184.60565
predicted
DeepCCS 1.0 (2019)
[M+H]+196.2312641
predicted
DarkChem Lite v0.1.0
[M+H]+187.25964
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.8325641
predicted
DarkChem Lite v0.1.0
[M+Na]+194.42082
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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. 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. [Article]
  2. 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. [Article]
  3. 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. [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. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. 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. [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. Zhou Q, Yan XF, Zhang ZM, Pan WS, Zeng S: Rational prescription of drugs within similar therapeutic or structural class for gastrointestinal disease treatment: drug metabolism and its related interactions. World J Gastroenterol. 2007 Nov 14;13(42):5618-28. [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
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, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
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. [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]
Kind
Protein
Organism
Humans
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
Uniprot Name
Canalicular multispecific organic anion transporter 1
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. [Article]
Kind
Protein
Organism
Humans
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...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

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