Chemical: Drug
gatifloxacin

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PharmGKB contains no Clinical Variants that meet the highest level of criteria.

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Overview

Generic Names
  • gatifloxacin
Trade Names
  • Tequin
  • Zymar
Brand Mixture Names

PharmGKB Accession Id

PA449738

Type(s):

Drug

Description

Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. Bristol-Myers Squibb introduced Gatifloxacin in 1999 under the proprietary name Tequin® for the treatment of respiratory tract infections, having licensed the medication from Kyorin Pharmaceutical Company of Japan. Allergan produces an eye-drop formulation called Zymar®. Gatifloxacin is available as tablets and in various aqueous solutions for intravenous therapy. Wikipedia

Source: Drug Bank

Indication

For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

The bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.

Source: Drug Bank

Pharmacology

Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. 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. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.

Source: Drug Bank

Food Interaction

Drink liberally.|Absorption does not seem to be affected by milk or calcium carbonate, however, gatifloxacin bioavailability appears significantly reduced when combined with Ensure tm (C max is reduced by about 50% while total drug exposure (AUC) is reduced by about 25%).|Take without regard to meals.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites

Source: Drug Bank

Protein Binding

20%

Source: Drug Bank

Absorption

Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%

Source: Drug Bank

Half-Life

7-14 hours

Source: Drug Bank

Chemical Properties

Chemical Formula

C19H22FN3O4

Source: Drug Bank

Isomeric SMILES

C[C@H]1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F

Source: Drug Bank

COC1=C(N2CCNC(C)C2)C(F)=CC2=C1N(C=C(C(O)=O)C2=O)C1CC1

Source: Drug Bank

Canonical SMILES

COC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC1

Source: Drug Bank

Average Molecular Weight

375.3941

Source: Drug Bank

Monoisotopic Molecular Weight

375.159434412

Source: Drug Bank

SMILES

COC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC1

Source: Drug Bank

InChI String

InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Curated Information ?

Drug Targets

Gene Description
ALB (source: Drug Bank)
TOP2A (source: Drug Bank)

Drug Interactions

Interaction Description
amiodarone - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
amiodarone - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
bepridil - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
bepridil - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
chlorpromazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
chlorpromazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
digoxin - gatifloxacin Gatifloxacin increases the effect of digoxin (source: Drug Bank)
digoxin - gatifloxacin Gatifloxacin increases the effect of digoxin (source: Drug Bank)
disopyramide - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
disopyramide - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
fluphenazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
fluphenazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - acenocoumarol Gatifloxacin increases the anticoagulant effect (source: Drug Bank)
gatifloxacin - aluminium Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - amiodarone Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - amiodarone Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - bepridil Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - bretylium Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - bretylium Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - chlorpromazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - chlorpromazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - dicumarol Gatifloxacin increases the anticoagulant effect (source: Drug Bank)
gatifloxacin - digoxin Gatifloxacin increases the effect of digoxin (source: Drug Bank)
gatifloxacin - digoxin Gatifloxacin increases the effect of digoxin (source: Drug Bank)
gatifloxacin - disopyramide Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - disopyramide Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - fluphenazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - fluphenazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - iron Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - iron Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - Magnesium Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - Magnesium Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - magnesium oxide Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - mesoridazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - mesoridazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - methotrimeprazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - perphenazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - perphenazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - prochlorperazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - prochlorperazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - promazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - promazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - promethazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - promethazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - propiomazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - quinidine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - quinidine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - quinupristin This combination presents an increased risk of toxicity (source: Drug Bank)
gatifloxacin - salicylate-magnesium Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - sotalol Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - sotalol Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - sucralfate Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - sucralfate Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - thiethylperazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - thioridazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - thioridazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - trifluoperazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - trifluoperazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - triflupromazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - triflupromazine Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
gatifloxacin - warfarin Gatifloxacin increases the anticoagulant effect (source: Drug Bank)
gatifloxacin - zinc Formation of non-absorbable complexes (source: Drug Bank)
gatifloxacin - zinc Formation of non-absorbable complexes (source: Drug Bank)
iron dextran - gatifloxacin Formation of non-absorbable complexes (source: Drug Bank)
Magnesium - gatifloxacin Formation of non-absorbable complexes (source: Drug Bank)
mesoridazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
mesoridazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
methotrimeprazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
perphenazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
perphenazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
prochlorperazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
prochlorperazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
promethazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
promethazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
quinidine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
quinidine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
quinupristin - gatifloxacin This combination presents an increased risk of toxicity (source: Drug Bank)
thioridazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
thioridazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
thiothixene - gatifloxacin May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration. (source: Drug Bank)
thiothixene - gatifloxacin May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration. (source: Drug Bank)
toremifene - gatifloxacin Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration. (source: Drug Bank)
trifluoperazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
trifluoperazine - gatifloxacin Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
trimipramine - gatifloxacin Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. (source: Drug Bank)
voriconazole - gatifloxacin Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). (source: Drug Bank)
vorinostat - gatifloxacin Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP). (source: Drug Bank)
ziprasidone - gatifloxacin Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated. (source: Drug Bank)

Publications related to gatifloxacin: 1

No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Xenobiotic transporters of the human organic anion transporting polypeptides (OATP) family. Xenobiotica; the fate of foreign compounds in biological systems. 2008. Hagenbuch B, et al. PubMed

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
0023-9218-05
DrugBank:
DB01044
ChEBI:
5280
KEGG Compound:
C07661
PubChem Compound:
5379
PubChem Substance:
46506159
9863
Drugs Product Database (DPD):
2243181
ChemSpider:
5186
Therapeutic Targets Database:
DAP001387
FDA Drug Label at DailyMed:
a5b0725e-9b7e-426b-ab1c-fcca3b1972fd

Clinical Trials

These are trials that mention gatifloxacin and are related to either pharmacogenetics or pharmacogenomics.

No trials found.

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Sources for PharmGKB drug information: DrugBank, PubChem.