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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Levofloxacin
- Accession Number
- DB01137 (APRD00477, DB06085)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.
- Structure
Structure for Levofloxacin (DB01137)
- Synonyms
- (-)-Ofloxacin
- (3S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid
- (S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylic acid
- (S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid
- (S)-Ofloxacin
- L-Ofloxacin
- Levofloxacin
- Levofloxacin anhydrous
- Levofloxacine
- Levofloxacino
- Levofloxacinum
- Ofloxacin S-(-)-form
- External IDs
- MP-376
- Product Ingredients
Ingredient UNII CAS InChI Key Levofloxacin hemihydrate 6GNT3Y5LMF 138199-71-0 SUIQUYDRLGGZOL-RCWTXCDDSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Act Levofloxacin Tablet 750 mg Oral Teva 2009-06-24 Not applicable Canada 
Act Levofloxacin Tablet 500 mg Oral Teva 2009-06-24 Not applicable Canada Act Levofloxacin Tablet 250 mg Oral Teva 2009-06-24 Not applicable Canada Iquix Solution 15 mg/1mL Ophthalmic Vistakon Pharmaceuticals 2004-06-01 2017-04-13 US 
Levaquin Tablet, film coated 500 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 1996-12-20 Not applicable US Levaquin Injection, solution 5 mg/1mL Intravenous McNeil Pharmaceuticals 1996-12-20 2011-12-31 US Levaquin Tablet, film coated 500 mg/1 Oral Rebel Distributors 1996-12-20 Not applicable US Levaquin Tablet, film coated 750 mg/1 Oral REMEDYREPACK INC. 2017-05-09 Not applicable US Levaquin Tablet, film coated 500 mg/1 Oral Physicians Total Care, Inc. 2000-05-11 Not applicable US 
Levaquin Tablet 250 mg Oral Janssen Pharmaceuticals 1997-11-28 2014-10-27 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Apo-levofloxacin Tablet 750 mg Oral Apotex Corporation 2009-06-24 Not applicable Canada Apo-levofloxacin Tablet 500 mg Oral Apotex Corporation 2009-06-24 Not applicable Canada Apo-levofloxacin Tablet 250 mg Oral Apotex Corporation 2009-06-24 Not applicable Canada Auro-levofloxacin Tablet 500 mg Oral Auro Pharma Inc 2016-04-12 Not applicable Canada Auro-levofloxacin Tablet 250 mg Oral Auro Pharma Inc 2016-04-12 Not applicable Canada Auro-levofloxacin Tablet 750 mg Oral Auro Pharma Inc 2016-04-12 Not applicable Canada Ava-levofloxacin Tablet 500 mg Oral Avanstra Inc 2011-09-15 2014-08-21 Canada Ava-levofloxacin Tablet 250 mg Oral Avanstra Inc 2011-09-15 2014-08-21 Canada Dom-levofloxacin Tablet 500 mg Oral Dominion Pharmacal Not applicable Not applicable Canada Dom-levofloxacin Tablet 250 mg Oral Dominion Pharmacal Not applicable Not applicable Canada - International/Other Brands
- Cravit / Elequine / Floxel / Leroxacin / Levokacin / Levox / Levoxacin / Mosardal / Nofaxin / Reskuin / Tavanic
- Categories
- Alimentary Tract and Metabolism
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Chemically-Induced Disorders
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 Enzyme Inhibitors
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Enzyme Inhibitors
- Fluoroquinolones
- MATE 1 Inhibitors
- MATE 1 Substrates
- MATE 2 Inhibitors
- MATE inhibitors
- MATE substrates
- Moderate Risk QTc-Prolonging Agents
- OCT2 Inhibitors
- Ofloxacin
- Ophthalmologicals
- P-glycoprotein/ABCB1 Inhibitors
- P-glycoprotein/ABCB1 Substrates
- QTc Prolonging Agents
- Quinolines
- Quinolone Antimicrobial
- Quinolones
- Renal Agents
- Sensory Organs
- Topoisomerase II Inhibitors
- Topoisomerase Inhibitors
- UNII
- RIX4E89Y14
- CAS number
- 100986-85-4
- Weight
- Average: 361.3675
Monoisotopic: 361.143784348 - Chemical Formula
- C18H20FN3O4
- InChI Key
- GSDSWSVVBLHKDQ-JTQLQIEISA-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)/t10-/m0/s1
- IUPAC Name
- (2S)-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
- C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1
Pharmacology
- Indication
For the treatment of bacterial conjunctivitis caused by susceptible strains of the following organisms: Corynebacterium species, Staphylococus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, Streptococcus (Groups C/F/G), Viridans group streptococci, Acinetobacter lwoffii, Haemophilus influenzae, Serratia marcescens.
- Associated Conditions
- Acute Bacterial Exacerbation of Chronic Bronchitis (ABECB)
- Acute Pyelonephritis
- Acute maxillary sinusitis caused by M. catarrhalis
- Anthrax
- Bacterial Infections
- Cellulitis
- Chlamydial Infections
- Community Acquired Pneumonia (CAP)
- Complicated Urinary Tract Infections
- Conjunctivitis, Bacterial
- Cystic fibrosis pulmonary exacerbation caused by Pseudomonas aeruginosa
- Diverticulitis
- Epididymitis
- Furuncle
- Impetigo
- Infected animal bite
- Infection, Postoperative Wound
- Legionella Pneumophila Infections
- Plague
- Prostatitis caused by Proteus mirabilis
- Prosthetic Joint Infection
- Pyoderma
- Travelers' Diarrhea
- Tuberculosis Infection
- Uncomplicated Urinary Tract Infections
- Urethritis
- Wound Infections
- Complicated Skin and subcutaneous tissue bacterial infection
- Hospital-acquired bacterial pneumonia
- Uncomplicated skin and subcutaneous tissue bacterial infections
- Pharmacodynamics
Levofloxacin, a fluoroquinolone antiinfective, is the optically active L-isomer of ofloxacin. Levofloxacin is used to treat bacterial conjunctivitis, sinusitis, chronic bronchitis, community-acquired pneumonia and pneumonia caused by penicillin-resistant strains of Streptococcus pneumoniae, skin and skin structure infections, complicated urinary tract infections and acute pyelonephritis.
- Mechanism of action
Levofloxacin inhibits bacterial type II topoisomerases, topoisomerase IV and DNA gyrase. Levofloxacin, like other fluoroquinolones, inhibits the A subunits of DNA gyrase, two subunits encoded by the gyrA gene. This results in strand breakage on a bacterial chromosome, supercoiling, and resealing; DNA replication and transcription is inhibited.
Target Actions Organism ADNA topoisomerase 4 subunit A inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) ADNA gyrase subunit A inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) ADNA topoisomerase 2-alpha inhibitorHumans - Absorption
Absorption of ofloxacin after single or multiple doses of 200 to 400 mg is predictable, and the amount of drug absorbed increases proportionately with the dose.
- Volume of distribution
- Not Available
- Protein binding
24-38% (to plasma proteins)
- Metabolism
Mainly excreted as unchanged drug (87%); undergoes limited metabolism in humans.
- Route of elimination
Mainly excreted as unchanged drug in the urine.
- Half life
6-8 hours
- Clearance
- Not Available
- Toxicity
Side effects include disorientation, dizziness, drowsiness, hot and cold flashes, nausea, slurring of speech, swelling and numbness in the face
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The therapeutic efficacy of (R)-warfarin can be increased when used in combination with Levofloxacin. (S)-Warfarin The therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Levofloxacin. 2,4-thiazolidinedione The therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Levofloxacin. 3-isobutyl-1-methyl-7H-xanthine The metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Levofloxacin. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Levofloxacin. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Levofloxacin. 5-androstenedione The metabolism of 5-androstenedione can be decreased when combined with Levofloxacin. 6-O-benzylguanine The metabolism of 6-O-benzylguanine can be decreased when combined with Levofloxacin. 7-Deazaguanine The metabolism of 7-Deazaguanine can be decreased when combined with Levofloxacin. 7-ethyl-10-hydroxycamptothecin The metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Levofloxacin. - Food Interactions
- Take without regard to meals. Take with water, drink lliberally. Taking this product with orange juice can result in reduced quinolone plasma levels.
References
- Synthesis Reference
Valerie Niddam-Hildesheim, "Preparation of levofloxacin and forms thereof." U.S. Patent US20030130507, issued July 10, 2003.
US20030130507- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001929
- KEGG Drug
- D08120
- KEGG Compound
- C07660
- PubChem Compound
- 149096
- PubChem Substance
- 46505134
- BindingDB
- 50366826
- ChEBI
- 63598
- ChEMBL
- CHEMBL33
- Therapeutic Targets Database
- DAP000160
- PharmGKB
- PA450214
- HET
- LFX
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Levofloxacin
- ATC Codes
- J01MA12 — Levofloxacin
- J01MA — Fluoroquinolones
- J01M — QUINOLONE ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- AHFS Codes
- 08:12.18 — Quinolones
- PDB Entries
- 3k9f / 3rae / 4juo / 4z2d / 5btg / 5bti / 5eix
- FDA label
- Download (139 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Advanced Pharmaceutical Services Inc.
- Apotheca Inc.
- A-S Medication Solutions LLC
- Atlantic Biologicals Corporation
- Cardinal Health
- Comprehensive Consultant Services Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- H.J. Harkins Co. Inc.
- Hospira Inc.
- Innoviant Pharmacy Inc.
- Janssen-Ortho Inc.
- Lake Erie Medical and Surgical Supply
- Letco Medical Inc.
- Liberty Pharmaceuticals
- McNeil Laboratories
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Neuman Distributors Inc.
- Nucare Pharmaceuticals Inc.
- OMJ Pharmaceuticals
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Ortho-McNeil-Janssen Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Prepackage Specialists
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Santen Inc.
- Southwood Pharmaceuticals
- Stat Rx Usa
- Teva Pharmaceutical Industries Ltd.
- Vistakon Pharmaceuticals LLC
- Yuhan Chemical Industrial Co. Ltd.
- Dosage forms
Form Route Strength Solution Ophthalmic 15 mg/1mL Injection, solution Intravenous 5 mg/1mL Injection, solution, concentrate Intravenous 25 mg/1mL Solution Oral 25 mg/1mL Tablet, film coated Oral 250 mg/1 Tablet, film coated Oral 500 mg/1 Tablet, film coated Oral 750 mg/1 Solution Intravenous 25 mg Solution Intravenous 5 mg Injection Intravenous 25 mg/1mL Injection Intravenous 5 mg/1mL Injection, solution Intravenous 25 mg/1mL Injection, solution Intravenous 250 mg/50mL Injection, solution Intravenous 500 mg/100mL Injection, solution Intravenous 750 mg/200mL Injection, solution Intravenous 750 mg/150mL Injection, solution, concentrate Intravenous 500 mg/20mL Injection, solution, concentrate Intravenous 750 mg/30mL Solution / drops Ophthalmic 5 mg/1mL Solution / drops Topical 5 mg/1mL Tablet Oral 250 mg/1 Tablet Oral 500 mg/1 Tablet Oral 750 mg/1 Tablet Oral 250 mg Tablet Oral 500 mg Solution Respiratory (inhalation) 240 mg Solution Ophthalmic 5 mg/1mL Tablet Oral 750 mg - Prices
Unit description Cost Unit Iquix 1.5% Solution 5ml Bottle 81.68USD bottle Levofloxacin hemihydr 100% powder 42.69USD g Levaquin 750 mg tablet 28.06USD each Levaquin 750 mg leva-pak tablet 27.51USD tablet Levaquin 500 mg tablet 16.57USD tablet Iquix 1.5% eye drops 15.71USD ml Levaquin 250 mg tablet 13.71USD tablet Quixin 0.5% eye drops 12.21USD ml Quixin 0.5% Solution 11.4USD ml Levaquin i.v. 25 mg/ml vial 1.94USD ml Levaquin 500 mg/100 ml d5w 0.44USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US5053407 No 1991-10-01 2010-12-20 US US6806256 Yes 2004-10-19 2022-08-26 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Insoluble Not Available logP 2.1 Not Available - Predicted Properties
Property Value Source Water Solubility 1.44 mg/mL ALOGPS logP -0.02 ALOGPS logP 0.65 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 5.45 ChemAxon pKa (Strongest Basic) 6.2 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- 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
- Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Benzoxazine / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives show 34 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- quinolone antibiotic, fluoroquinolone antibiotic, ofloxacin (CHEBI:63598)
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
- Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
- Gene Name
- parC
- Uniprot ID
- P43702
- Uniprot Name
- DNA topoisomerase 4 subunit A
- Molecular Weight
- 83366.24 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- 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]
- Zheng X, Johnson C, Lu Y, Yanagihara R, Hollingshead S, Crain M, Benjamin W Jr, Waites KB: Clinical isolates of Streptococcus pneumoniae resistant to levofloxacin contain mutations in both gyrA and parC genes. Int J Antimicrob Agents. 2001 Oct;18(4):373-8. [PubMed:11691571]
- Schafer J, Hovde LB, Simonson D, Rotschafer JC: In vitro pharmacodynamics of moxifloxacin versus levofloxacin against 4 strains of Streptococcus pneumoniae: 1 wild type, 2 first-step parC mutants, and 1 pump mutant. Diagn Microbiol Infect Dis. 2008 Feb;60(2):155-61. Epub 2007 Oct 29. [PubMed:17910998]
- Deryke CA, Du X, Nicolau DP: Evaluation of bacterial kill when modelling the bronchopulmonary pharmacokinetic profile of moxifloxacin and levofloxacin against parC-containing isolates of Streptococcus pneumoniae. J Antimicrob Chemother. 2006 Sep;58(3):601-9. Epub 2006 Jul 19. [PubMed:16857688]
- Kind
- Protein
- Organism
- Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dna topoisomerase type ii (atp-hydrolyzing) activity
- Specific Function
- DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
- Gene Name
- gyrA
- Uniprot ID
- P43700
- Uniprot Name
- DNA gyrase subunit A
- Molecular Weight
- 97817.145 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- 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]
- 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]
- Brisse S, Milatovic D, Fluit AC, Verhoef J, Martin N, Scheuring S, Kohrer K, Schmitz FJ: Comparative in vitro activities of ciprofloxacin, clinafloxacin, gatifloxacin, levofloxacin, moxifloxacin, and trovafloxacin against Klebsiella pneumoniae, Klebsiella oxytoca, Enterobacter cloacae, and Enterobacter aerogenes clinical isolates with alterations in GyrA and ParC proteins. Antimicrob Agents Chemother. 1999 Aug;43(8):2051-5. [PubMed:10428935]
- Messina C, Cafiso V, Campanile F, Santagati M, Stefani S: Rapid method for detection of gyrA and grlA mutations in unrelated strains of Staphylococci susceptible and resistant to levofloxacin. New Microbiol. 2001 Oct;24(4):347-53. [PubMed:11718372]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Ubiquitin binding
- Specific Function
- Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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
- Bellon A, Perez-Garcia G, Coverdale JH, Chacko RC: Seizures associated with levofloxacin: case presentation and literature review. Eur J Clin Pharmacol. 2009 Oct;65(10):959-62. doi: 10.1007/s00228-009-0717-5. Epub 2009 Aug 26. [PubMed:19707748]
- 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]
- Shahzadi A, Javed I, Aslam B, Muhammad F, Asi MR, Ashraf MY, Zia-ur-Rahman: Therapeutic effects of ciprofloxacin on the pharmacokinetics of carbamazepine in healthy adult male volunteers. Pak J Pharm Sci. 2011 Jan;24(1):63-8. [PubMed:21190921]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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]
- Nakamura H, Ohtsuka T, Enomoto H, Hasegawa A, Kawana H, Kuriyama T, Ohmori S, Kitada M: Effect of levofloxacin on theophylline clearance during theophylline and clarithromycin combination therapy. Ann Pharmacother. 2001 Jun;35(6):691-3. doi: 10.1345/aph.10307. [PubMed:11408986]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Ito T, Yano I, Tanaka K, Inui KI: Transport of quinolone antibacterial drugs by human P-glycoprotein expressed in a kidney epithelial cell line, LLC-PK1. J Pharmacol Exp Ther. 1997 Aug;282(2):955-60. [PubMed:9262363]
- Yamaguchi H, Yano I, Hashimoto Y, Inui KI: Secretory mechanisms of grepafloxacin and levofloxacin in the human intestinal cell line caco-2. J Pharmacol Exp Ther. 2000 Oct;295(1):360-6. [PubMed:10992002]
- Yamaguchi H, Yano I, Saito H, Inui K: Effect of cisplatin-induced acute renal failure on bioavailability and intestinal secretion of quinolone antibacterial drugs in rats. Pharm Res. 2004 Feb;21(2):330-8. [PubMed:15032316]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Uwai Y, Okuda M, Takami K, Hashimoto Y, Inui K: Functional characterization of the rat multispecific organic anion transporter OAT1 mediating basolateral uptake of anionic drugs in the kidney. FEBS Lett. 1998 Nov 6;438(3):321-4. [PubMed:9827570]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365]
- Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [PubMed:10082798]
- 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
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [PubMed:17509534]
- Nies AT, Damme K, Schaeffeler E, Schwab M: Multidrug and toxin extrusion proteins as transporters of antimicrobial drugs. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1565-77. doi: 10.1517/17425255.2012.722996. Epub 2012 Sep 13. [PubMed:22970772]
- Ohta KY, Imamura Y, Okudaira N, Atsumi R, Inoue K, Yuasa H: Functional characterization of multidrug and toxin extrusion protein 1 as a facilitative transporter for fluoroquinolones. J Pharmacol Exp Ther. 2009 Feb;328(2):628-34. doi: 10.1124/jpet.108.142257. Epub 2008 Nov 12. [PubMed:19004926]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data for this transporter inhibition are limited to an in vitro study.
- General Function
- Drug transmembrane transporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
- Gene Name
- SLC47A2
- Uniprot ID
- Q86VL8
- Uniprot Name
- Multidrug and toxin extrusion protein 2
- Molecular Weight
- 65083.915 Da
References
- Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [PubMed:17509534]
Drug created on June 13, 2005 07:24 / Updated on February 18, 2019 20:23