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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
Structure for Ofloxacin (DB01165)
- 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.
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 Acute bacterial exacerbation of chronic bronchitis •••••••••••• Treatment of Acute otitis media •••••••••••• Treatment of Bacterial infections •••••••••••• Treatment of Cervicitis •••••••••••• Treatment of Community-acquired pneumonia •••••••••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism ADNA gyrase subunit A inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) ADNA gyrase subunit B modulatorStaphylococcus aureus ADNA gyrase subunit A modulatorStaphylococcus aureus ADNA topoisomerase 4 subunit A inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) UDNA topoisomerase 2-alpha inhibitorHumans - 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcamprosate The excretion of Acamprosate can be decreased when combined with Ofloxacin. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Ofloxacin. Aceclofenac Aceclofenac may increase the neuroexcitatory activities of Ofloxacin. Acemetacin Acemetacin may increase the neuroexcitatory activities of Ofloxacin. Acenocoumarol The therapeutic efficacy of Acenocoumarol 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
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 Ofloxacin hydrochloride I2UWV315WA 118120-51-7 CAOOISJXWZMLBN-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Floxstat / Zanocin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Floxin Tablet, coated 400 mg/1 Oral Ortho Mc Neil Pharmaceuticals 1990-12-28 2009-01-31 US 
Floxin Tablet, coated 300 mg/1 Oral Physicians Total Care, Inc. 1995-04-25 2011-05-31 US Floxin Tablet, coated 300 mg/1 Oral Ortho Mc Neil Pharmaceuticals 1990-12-28 2009-01-31 US Floxin Tablet, coated 200 mg/1 Oral Physicians Total Care, Inc. 1993-08-03 2011-05-31 US Floxin Tablet, coated 400 mg/1 Oral Physicians Total Care, Inc. 1992-12-08 2011-05-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-ofloxacin Solution 0.3 % Ophthalmic Apotex Corporation 2004-01-22 Not applicable Canada 
Floxin Otic Solution / drops 3 mg/1mL Auricular (otic) Almatica Pharma LLC 2016-07-25 2019-11-15 US Novo-ofloxacin Tablet 400 mg Oral Novopharm Limited 2004-06-11 2012-05-08 Canada Novo-ofloxacin Tablet 300 mg Oral Novopharm Limited 2004-06-11 2012-05-08 Canada Novo-ofloxacin Tablet 200 mg Oral Novopharm Limited 2004-06-11 2012-05-08 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image EXOPRED (OPHTHALMIC SUSPENSION) Ofloxacin (3 MG/1ML) + Prednisolone (10 MG/1ML) Suspension Ophthalmic บริษัท แอลเลอร์แกน (ประเทศไทย) จำกัด 2016-07-14 Not applicable Thailand 
Categories
- ATC Codes
- J01MA01 — Ofloxacin
- J01MA — Fluoroquinolones
- J01M — QUINOLONE ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Agents Causing Muscle Toxicity
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- BSEP/ABCB11 Substrates
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Fluoroquinolones
- Heterocyclic Compounds, Fused-Ring
- Moderate Risk QTc-Prolonging Agents
- OAT1/SLC22A6 inhibitors
- Ophthalmologicals
- Otologicals
- QTc Prolonging Agents
- Quinolines
- Quinolone Antimicrobial
- Quinolones
- Sensory Organs
- 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
- 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
- External Links
- Human Metabolome Database
- HMDB0015296
- KEGG Drug
- D00453
- KEGG Compound
- C07321
- PubChem Compound
- 4583
- PubChem Substance
- 46507574
- ChemSpider
- 4422
- BindingDB
- 50045004
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide Not Available Completed Diagnostic Unexplained Infertility 1 somestatus stop reason just information to hide Not Available Completed Prevention Epistaxis / Intubation 1 somestatus stop reason just information to hide Not Available Completed Treatment Acute Otitis Media (AOM) 1 somestatus stop reason just information to hide Not Available Completed Treatment Myopia (Disorder) / Refractive Errors 1 somestatus stop reason just information to hide
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
Form Route Strength Solution Auricular (otic) Ointment Ophthalmic 0.3 % Solution / drops Ophthalmic 3 MG/ML Suspension Ophthalmic Tablet Oral Tablet Oral 400.00 mg Tablet, film coated Oral 200.00 MG Ointment Ophthalmic Tablet, coated Oral 200 mg/1 Tablet, coated Oral 300 mg/1 Tablet, coated Oral 400 mg/1 Liquid Intravenous 20 mg / mL Tablet Oral 300 mg Tablet Oral 400 mg Solution Intravenous 400 mg Tablet, coated Oral 400 mg Solution / drops Auricular (otic) 0.3 % Tablet, coated Oral 100 mg Tablet Oral 400.000 mg Solution Auricular (otic) Injection, solution Intravenous 200 mg/100ml Solution / drops Ophthalmic 0.3 % Solution Ophthalmic 0.3 % Solution Ophthalmic 3.000 mg Tablet Oral 200 mg Solution Auricular (otic) 3 mg Tablet, coated Oral Solution Conjunctival; Ophthalmic 3 mg Injection Intravenous 2 MG/ML Solution Auricular (otic) 3 mg/1mL Solution Ophthalmic 3 mg/1mL Solution / drops Auricular (otic) 3 mg/1mL Solution / drops Ophthalmic 3 mg/1mL Tablet Oral 200 mg/1 Tablet Oral 300 mg/1 Tablet Oral 400 mg/1 Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 300 mg/1 Tablet, film coated Oral 400 mg/1 Tablet, film coated Oral Solution / drops Ophthalmic Injection Intravenous 200 mg/100ml Solution / drops Auricular (otic) Solution Oral 3 mg Tablet, film coated Oral 200 mg Injection, solution Intravenous Tablet, film coated Oral 400 mg Solution / drops Auricular (otic) 3 mg/ml Solution / drops Ophthalmic 3 mg Solution Auricular (otic) 3 mg/ml Solution / drops Auricular (otic) 3 mg Solution Intravenous 200 mg Tablet, coated Oral 300 mg Liquid Auricular (otic) 3 mg/1ml Liquid Ophthalmic 3 mg/1ml Tablet, coated Oral 200 mg Tablet, film coated Oral 100 mg Tablet Oral 100 mg Solution 2 mg/1ml Capsule 100 mg - Prices
Unit description Cost Unit Floxin Otic 0.3% Solution 10ml Bottle 142.91USD bottle Ofloxacin 10ml Otic (ear) Solution 132.19USD bottle Ofloxacin 10ml. Ophthalmic (eye) Solution 87.6USD bottle Floxin Otic 0.3% Solution 5ml Bottle 86.49USD bottle Ofloxacin 5ml Otic (ear) Solution 77.21USD bottle Ofloxacin 5ml. Ophthalmic (eye) Solution 43.86USD bottle Ocuflox 0.3% eye drops 11.35USD ml Floxin 400 mg tablet 9.55USD tablet Ofloxacin 0.3% eye drops 8.08USD ml Floxin 200 mg tablet 6.6USD tablet Ofloxacin 400 mg tablet 6.12USD tablet Ofloxacin 300 mg tablet 5.81USD tablet Floxin 300 mg tablet 5.61USD tablet Ofloxacin 200 mg tablet 4.88USD tablet Floxin otic singles 4.28USD each Ocuflox 0.3 % Solution 2.75USD ml Apo-Ofloxacin 0.3 % Solution 1.04USD ml Pms-Ofloxacin 0.3 % Solution 1.04USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5401741 No 1995-03-28 2012-03-27 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 254 dec °C PhysProp water solubility 28.3 mg/mL Not Available logP -0.39 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 1.44 mg/mL ALOGPS logP -0.02 ALOGPS logP 0.09 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 5.35 Chemaxon pKa (Strongest Basic) 6.72 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 73.32 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 94.94 m3·mol-1 Chemaxon Polarizability 36.69 Å3 Chemaxon Number of Rings 4 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 + 0.9545 Blood Brain Barrier - 0.9659 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.7862 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.8383 Renal organic cation transporter Non-inhibitor 0.7489 CYP450 2C9 substrate Non-substrate 0.8468 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6386 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9268 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7726 Ames test AMES toxic 0.7844 Carcinogenicity Non-carcinogens 0.9033 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.1639 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8402 hERG inhibition (predictor II) Non-inhibitor 0.866
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 195.5502641 predictedDarkChem Lite v0.1.0 [M-H]- 184.60565 predictedDeepCCS 1.0 (2019) [M+H]+ 196.2312641 predictedDarkChem Lite v0.1.0 [M+H]+ 187.25964 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.8325641 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.42082 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights 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
- A type II topoisomerase that negatively supercoils closed circular double-stranded (ds) DNA in an ATP-dependent manner to modulate DNA topology and maintain chromosomes in an underwound state. Negative supercoiling favors strand separation, and DNA replication, transcription, recombination and repair, all of which involve strand separation. Also able to catalyze the interconversion of other topological isomers of dsDNA rings, including catenanes and knotted rings. Type II topoisomerases break and join 2 DNA strands simultaneously in an ATP-dependent manner.
- Specific Function
- ATP binding
- Gene Name
- gyrA
- Uniprot ID
- P43700
- Uniprot Name
- DNA gyrase subunit A
- Molecular Weight
- 97817.145 Da
References
- 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]
- 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]
- 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
- Staphylococcus aureus
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- A type II topoisomerase that negatively supercoils closed circular double-stranded (ds) DNA in an ATP-dependent manner to modulate DNA topology and maintain chromosomes in an underwound state. Negative supercoiling favors strand separation, and DNA replication, transcription, recombination and repair, all of which involve strand separation. Also able to catalyze the interconversion of other topological isomers of dsDNA rings, including catenanes and knotted rings. Type II topoisomerases break and join 2 DNA strands simultaneously in an ATP-dependent manner.
- Specific Function
- ATP binding
- Gene Name
- gyrB
- Uniprot ID
- P0A0K8
- Uniprot Name
- DNA gyrase subunit B
- Molecular Weight
- 72539.365 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- A type II topoisomerase that negatively supercoils closed circular double-stranded (ds) DNA in an ATP-dependent manner to modulate DNA topology and maintain chromosomes in an underwound state. Negative supercoiling favors strand separation, and DNA replication, transcription, recombination and repair, all of which involve strand separation. Also able to catalyze the interconversion of other topological isomers of dsDNA rings, including catenanes and knotted rings. Type II topoisomerases break and join 2 DNA strands simultaneously in an ATP-dependent manner.
- Specific Function
- ATP binding
- Gene Name
- gyrA
- Uniprot ID
- P20831
- Uniprot Name
- DNA gyrase subunit A
- Molecular Weight
- 99620.34 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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.
- Specific Function
- ATP binding
- Gene Name
- parC
- Uniprot ID
- P43702
- Uniprot Name
- DNA topoisomerase 4 subunit A
- Molecular Weight
- 83366.24 Da
References
- 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]
- 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]
- 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]
- 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
- Key decatenating enzyme that alters DNA topology by binding to two double-stranded DNA molecules, generating a double-stranded break in one of the strands, passing the intact strand through the broken strand, and religating the broken strand (PubMed:17567603, PubMed:18790802, PubMed:22013166, PubMed:22323612). May play a role in regulating the period length of BMAL1 transcriptional oscillation (By similarity)
- Specific Function
- ATP binding
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 Da
References
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
References
- 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]
- 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
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- (R)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Organic cation/carnitine transporter 2
- Molecular Weight
- 62751.08 Da
References
- 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
- Mediates export of organic anions and drugs from the cytoplasm (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Confers resistance to anticancer drugs by decreasing accumulation of drug in cells, and by mediating ATP- and GSH-dependent drug export (PubMed:9281595). Hydrolyzes ATP with low efficiency (PubMed:16230346). Catalyzes the export of sphingosine 1-phosphate from mast cells independently of their degranulation (PubMed:17050692). Participates in inflammatory response by allowing export of leukotriene C4 from leukotriene C4-synthezing cells (By similarity). Mediates ATP-dependent, GSH-independent cyclic GMP-AMP (cGAMP) export (PubMed:36070769). Thus, by limiting intracellular cGAMP concentrations negatively regulates the cGAS-STING pathway (PubMed:36070769)
- Specific Function
- ABC-type glutathione S-conjugate transporter activity
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- 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
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- 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
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that binds and hydrolyzes ATP to enable active transport of various substrates including many drugs, toxicants and endogenous compound across cell membranes. Transports a wide variety of conjugated organic anions such as sulfate-, glucuronide- and glutathione (GSH)-conjugates of endo- and xenobiotics substrates (PubMed:10220572, PubMed:10421658, PubMed:11500505, PubMed:16332456). Mediates hepatobiliary excretion of mono- and bis-glucuronidated bilirubin molecules and therefore play an important role in bilirubin detoxification (PubMed:10421658). Mediates also hepatobiliary excretion of others glucuronide conjugates such as 17beta-estradiol 17-glucosiduronic acid and leukotriene C4 (PubMed:11500505). Transports sulfated bile salt such as taurolithocholate sulfate (PubMed:16332456). Transports various anticancer drugs, such as anthracycline, vinca alkaloid and methotrexate and HIV-drugs such as protease inhibitors (PubMed:10220572, PubMed:11500505, PubMed:12441801). Confers resistance to several anti-cancer drugs including cisplatin, doxorubicin, epirubicin, methotrexate, etoposide and vincristine (PubMed:10220572, PubMed:11500505)
- Specific Function
- ABC-type glutathione S-conjugate transporter activity
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- ATP-binding cassette sub-family C member 2
- Molecular Weight
- 174205.64 Da
References
- 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
- Transporter that mediates the transport of endogenous and microbial zwitterions and organic cations (PubMed:10215651, PubMed:15107849, PubMed:15795384, PubMed:16729965, PubMed:20601551, PubMed:22206629, PubMed:22569296, PubMed:29530864). Functions as a Na(+)-dependent and pH-dependent high affinity microbial symporter of potent food-derived antioxidant ergothioeine (PubMed:15795384, PubMed:29530864, PubMed:33124720). Transports one sodium ion with one ergothioeine molecule (By similarity). Involved in the absorption of ergothioneine from the luminal/apical side of the small intestine and renal tubular cells, and into non-parenchymal liver cells, thereby contributing to maintain steady-state ergothioneine level in the body (PubMed:20601551). Also mediates the bidirectional transport of acetycholine, although the exact transport mechanism has not been fully identified yet (PubMed:22206629). Most likely exports anti-inflammatory acetylcholine in non-neuronal tissues, thereby contributing to the non-neuronal cholinergic system (PubMed:22206629, PubMed:22569296). Displays a general physiological role linked to better survival by controlling inflammation and oxidative stress, which may be related to ergothioneine and acetycholine transports (PubMed:15795384, PubMed:22206629). May also function as a low-affinity Na(+)-dependent transporter of L-carnitine through the mitochondrial membrane, thereby maintaining intracellular carnitine homeostasis (PubMed:10215651, PubMed:15107849, PubMed:16729965). May contribute to regulate the transport of cationic compounds in testis across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- acetylcholine transmembrane transporter activity
- Gene Name
- SLC22A4
- Uniprot ID
- Q9H015
- Uniprot Name
- Solute carrier family 22 member 4
- Molecular Weight
- 62154.48 Da
References
- 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
- Catalyzes the transport of the major hydrophobic bile salts, such as taurine and glycine-conjugated cholic acid across the canalicular membrane of hepatocytes in an ATP-dependent manner, therefore participates in hepatic bile acid homeostasis and consequently to lipid homeostasis through regulation of biliary lipid secretion in a bile salts dependent manner (PubMed:15791618, PubMed:16332456, PubMed:18985798, PubMed:19228692, PubMed:20010382, PubMed:20398791, PubMed:22262466, PubMed:24711118, PubMed:29507376, PubMed:32203132). Transports taurine-conjugated bile salts more rapidly than glycine-conjugated bile salts (PubMed:16332456). Also transports non-bile acid compounds, such as pravastatin and fexofenadine in an ATP-dependent manner and may be involved in their biliary excretion (PubMed:15901796, PubMed:18245269)
- Specific Function
- ABC-type bile acid transporter activity
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- 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 October 11, 2024 18:19