QuickView for Moxifloxacin (compound)

Summary
General Info

PubChem

PubChem Compound 101526

Name:	moxifloxacin
PubChem Compound ID:	101526
Molecular formula:	C₂₁H₂₅ClFN₃O₄
Molecular weight:	437.892 g/mol
Synonyms:	3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-((4aS,7aS)-octahydro-6H-pyrrolo(3,4-b)pyridin-6-yl)-4-oxo-, monohydrochloride; Izilox; Vegamox; BAY 12-8039; Moxifloxacin hydrochloride [USAN]; Moxiflocacin hydrochloride; Moxifloxacin hydrochloride; 186826-86-8; Actira; LS-173737. show more » 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-((4aS,7aS)-octahydro-6H-pyrrolo(3,4-b)pyridin-6-yl)-4-oxo-, monohydrochloride; Izilox; Vegamox; BAY 12-8039; Moxifloxacin hydrochloride [USAN]; Moxiflocacin hydrochloride; Moxifloxacin hydrochloride; 186826-86-8; Actira; LS-173737; Vigamox; Bay-12-8039; Proflox; Avelox; Avalox; Octegra show less «

DrugBank

Identification

Name:	moxifloxacin
Name (isomeric):	DB00218
Drug Type:	small molecule
Synonyms:	Moxifloxacin hydrochloride; Moxifloxacin HCl; BAY 12-8039
Brand:	Avelox I.V., Avelox, Vigamox
Category:	Anti-Bacterial Agents, Anti-Infective Agents, Quinolones
CAS number:	354812-41-2

Pharmacology

Indication:	For the treatment of sinus and lung infections such as sinusitis, pneumonia, and secondary infections in chronic bronchitis. Also for the treatment of bacterial conjunctivitis (pinkeye).
Pharmacology:	Moxifloxacin is a quinolone/fluoroquinolone antibiotic. Moxifloxacin can be used to treat infections caused by the following bacteria: Aerobic Gram-positive microorganisms: Corynebacterium species, Micrococcus luteus, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus haemolyticus, Staphylococcus... show more » Moxifloxacin is a quinolone/fluoroquinolone antibiotic. Moxifloxacin can be used to treat infections caused by the following bacteria: Aerobic Gram-positive microorganisms: Corynebacterium species, Micrococcus luteus, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus haemolyticus, Staphylococcus hominis, Staphylococcus warneri, Streptococcus pneumoniae, and Streptococcus viridans group. Aerobic Gram-negative microorganisms: Acinetobacter lwoffii, Haemophilus influenzae, and Haemophilus parainfluenzae. Other microorganisms: Chlamydia trachomatis. Moxifloxacin 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. Moxifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. show less «
Mechanism of Action:	The bactericidal action of moxifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV. DNA gyrase is an essential enzyme that is involved in the replication, transcription and repair of bacterial DNA. Topoisomerase IV is an enzyme known to play a key role in the partitioning of the chromosomal DNA during ... show more » The bactericidal action of moxifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV. DNA gyrase is an essential enzyme that is involved in the replication, transcription and repair of bacterial DNA. Topoisomerase IV is an enzyme known to play a key role in the partitioning of the chromosomal DNA during bacterial cell division. show less «
Absorption:	Well absorbed from the gastrointestinal tract. Absolute oral bioavailability is approximately 90%. Food has little effect on absorption.
Protein binding:	50% bound to serum proteins, independent of drug concentration.
Biotransformation:	Approximately 52% or oral or intravenous dose is metabolized via glucuronide and sulphate conjugation. The cytochrome P450 system is not involved in metabolism. The sulphate conjugate accounts for 38% of the dose, and the glucuronide conjugate accounts for 14% of the dose.
Route of elimination:	Approximately 45% of an oral or intravenous dose of moxifloxacin is excreted as unchanged drug (~20% in urine and ~25% in feces).
Half Life:	11.5-15.6 hours (single dose, oral)
Clearance:	12 +/- 2 L/hr
Toxicity:	Symptoms of overdose include CNS and gastrointestinal effects such as decreased activity, somnolence, tremor, convulsions, vomiting, and diarrhea. The minimal lethal intravenous dose in mice and rats is 100 mg/kg.
Affected organisms:	Enteric bacteria and other eubacteria

Interactions

Food interaction:

Take without regard to meals. Drink liberally. Absorption is not affected by lipid-rich meals or yogourt.

Drug interaction:

Erythromycin	Increased risk of cardiotoxicity and arrhythmias
Disopyramide	Increased risk of cardiotoxicity and arrhythmias
Iron	Formation of non-absorbable complexes
Calcium	Formation of non-absorbable complexes
Bretylium	Increased risk of cardiotoxicity and arrhythmias

Erythromycin	Increased risk of cardiotoxicity and arrhythmias
Disopyramide	Increased risk of cardiotoxicity and arrhythmias
Iron	Formation of non-absorbable complexes
Calcium	Formation of non-absorbable complexes
Bretylium	Increased risk of cardiotoxicity and arrhythmias
Magnesium oxide	Formation of non-absorbable complexes
Zinc	Formation of non-absorbable complexes
Sucralfate	Formation of non-absorbable complexes
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Magnesium	Formation of non-absorbable complexes
Dihydroquinidine barbiturate	Increased risk of cardiotoxicity and arrhythmias
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Josamycin	Increased risk of cardiotoxicity and arrhythmias
Sotalol	Increased risk of cardiotoxicity and arrhythmias
Warfarin	The quinolone antibiotic, moxifloxacin, may increase the anticoagulant effect of warfarin.
Aluminium	Formation of non-absorbable complexes
Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Bepridil	Increased risk of cardiotoxicity and arrhythmias
Dicumarol	The quinolone antibiotic, moxifloxacin, may increase the anticoagulant effect of dicumarol.
Quinidine barbiturate	Increased risk of cardiotoxicity and arrhythmias
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
Quinupristin	This combination presents an increased risk of toxicity
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Acenocoumarol	The quinolone antibiotic, moxifloxacin, may increase the anticoagulant effect of acenocoumarol.
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Amiodarone	Increased risk of cardiotoxicity and arrhythmias
Toremifene	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.
Quinidine	Increased risk of cardiotoxicity and arrhythmias
Anisindione	The quinolone antibiotic, moxifloxacin, may increase the anticoagulant effect of anisindione.
Iron Dextran	Formation of non-absorbable complexes
Tizanidine	Moxifloxacin may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Voriconazole	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).

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Targets

DNA topoisomerase 4 subunit A

DNA gyrase subunit A

DNA topoisomerase 2-alpha