Identification

Name
Moxifloxacin
Accession Number
DB00218  (APRD00281)
Type
Small Molecule
Groups
Approved, Investigational
Description

Moxifloxacin is a synthetic fluoroquinolone antibiotic agent. Bayer AG developed the drug (initially called BAY 12-8039) and it is marketed worldwide (as the hydrochloride) under the brand name Avelox (in some countries also Avalox) for oral treatment.

Structure
Thumb
Synonyms
  • 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-((4as,7as)-octahydro-6H-pyrrolo(3,4-b)pyridin-6-yl)-4-oxo-3-quinolinecarboxylic acid
  • Moxifloxacin
  • Moxifloxacino
External IDs
BAY 12-8039
Product Ingredients
IngredientUNIICASInChI Key
Moxifloxacin hydrochlorideC53598599T186826-86-8IDIIJJHBXUESQI-DFIJPDEKSA-N
Moxifloxacin hydrochloride monohydrateB8956S8609192927-63-2SKZIMSDWAIZNDD-WJMOHVQJSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act MoxifloxacinSolution0.5 %OphthalmicActavis Pharma Company2015-11-04Not applicableCanada
AveloxTablet400 mgOralBayer2000-10-20Not applicableCanada
AveloxTablet, film coated400 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2011-12-07Not applicableUs
AveloxInjection, solution400 mg/250mLIntravenousBayer HealthCare Pharmaceuticals Inc.2001-11-30Not applicableUs
AveloxInjection, solution400 mg/250mLIntravenousSchering Plough2001-11-30Not applicableUs
AveloxTablet, film coated400 mg/1OralRed Pharm Drug, Inc.2011-02-25Not applicableUs67296 015420180907 15195 6lgyze
AveloxTablet, film coated400 mg/1OralRemedy Repack2013-05-242017-03-01Us00085 1733 03 nlmimage10 2619935c
AveloxTablet, film coated400 mg/1OralBayer HealthCare Pharmaceuticals Inc.1999-12-10Not applicableUs
AveloxTablet, film coated400 mg/1OralSchering Plough1999-12-10Not applicableUs0085 173320180814 13942 52ev3k
AveloxTablet, film coated400 mg/1OralPd Rx Pharmaceuticals, Inc.1999-12-102018-08-02Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-moxifloxacinTablet400 mgOralApotex Corporation2016-01-11Not applicableCanada
Apo-moxifloxacinSolution0.5 %OphthalmicApotex Corporation2015-11-19Not applicableCanada
Auro-moxifloxacinTablet400 mgOralAuro Pharma Inc2015-11-04Not applicableCanada
Bio-moxifloxacinTablet400 mgOralBiomed Pharma2016-01-15Not applicableCanada
Dom-moxifloxacinTablet400 mgOralDominion PharmacalNot applicableNot applicableCanada
Ipg-moxifloxacinTablet400 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-moxifloxacinSolution0.5 %OphthalmicJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-moxifloxacinTablet400 mgOralJamp Pharma Corporation2015-11-04Not applicableCanada
Jamp-moxifloxacin TabletsTablet400 mgOralJamp Pharma Corporation2016-01-11Not applicableCanada
Mar-moxifloxacinTablet400 mgOralMarcan Pharmaceuticals Inc2015-12-21Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Dex-MoxiMoxifloxacin hydrochloride monohydrate (5 mg/1mL) + Dexamethasone sodium phosphate (1 mg/1mL)Injection, solutionOphthalmicImprimis Njof, Llc2018-01-05Not applicableUs
Dex-Moxi PFMoxifloxacin hydrochloride monohydrate (5 mg/1mL) + Dexamethasone sodium phosphate (1 mg/1mL)Injection, solutionIntraocularImprimisRx NJ2018-01-01Not applicableUs
Dex-Moxi-KetorMoxifloxacin hydrochloride monohydrate (0.5 mg/1mL) + Dexamethasone sodium phosphate (1 mg/1mL) + Ketorolac tromethamine (0.4 mg/1mL)Injection, solutionOphthalmicImprimis Njof, Llc2018-01-05Not applicableUs
DexMoxiKetor PFMoxifloxacin hydrochloride monohydrate (0.5 mg/1mL) + Dexamethasone sodium phosphate (1 mg/1mL) + Ketorolac tromethamine (0.4 mg/1mL)Injection, solutionIntraocularImprimisRx NJ2018-01-01Not applicableUs
Moxifloxacin PFMoxifloxacin hydrochloride monohydrate (5 mg/1mL)Injection, solutionIntraocularImprimisRx NJ2018-01-01Not applicableUs
Moxifloxacin PFMoxifloxacin hydrochloride monohydrate (5 mg/1mL)Injection, solutionOphthalmicImprimis Njof, Llc2018-01-05Not applicableUs
Triamcinolone-Moxifloxacin PFMoxifloxacin hydrochloride (1 mg/1mL) + Triamcinolone acetonide (15 mg/1mL)SuspensionOphthalmicImprimisRx NJ2018-01-01Not applicableUs
Triamcinolone-Moxifloxacin PFMoxifloxacin hydrochloride monohydrate (1 mg/1mL) + Triamcinolone acetonide (15 mg/1mL)Injection, suspensionOphthalmicImprimis Njof, Llc2018-01-05Not applicableUs
Categories
UNII
U188XYD42P
CAS number
151096-09-2
Weight
Average: 401.4314
Monoisotopic: 401.175084476
Chemical Formula
C21H24FN3O4
InChI Key
FABPRXSRWADJSP-MEDUHNTESA-N
InChI
InChI=1S/C21H24FN3O4/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,16+/m0/s1
IUPAC Name
7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
[H][C@]12CN(C[C@@]1([H])NCCC2)C1=C(F)C=C2C(=O)C(=CN(C3CC3)C2=C1OC)C(O)=O

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).

Associated Conditions
Pharmacodynamics

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.

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 bacterial cell division.

TargetActionsOrganism
ADNA topoisomerase 4 subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA gyrase subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
UDNA topoisomerase 2-alpha
inhibitor
Human
Absorption

Well absorbed from the gastrointestinal tract. Absolute oral bioavailability is approximately 90%. Food has little effect on absorption.

Volume of distribution
  • 1.7 to 2.7 L/kg
Protein binding

50% bound to serum proteins, independent of drug concentration.

Metabolism

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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Moxifloxacin.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Moxifloxacin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Moxifloxacin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Moxifloxacin.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Moxifloxacin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Moxifloxacin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Moxifloxacin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Moxifloxacin.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Moxifloxacin.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Moxifloxacin.
Food Interactions
  • Take without regard to meals. Drink liberally. Absorption is not affected by lipid-rich meals or yogourt.

References

Synthesis Reference

Manne Reddy, Sajja Eswaraiah, Vetukuri Venkata Naga Raju, Rapolu Kumar, Ningam Srinivasreddy, Vedantham Ravindra, "Crystalline form III of anhydrous moxifloxacin hydrochloride and a process for preparation thereof." U.S. Patent US20050137227, issued June 23, 2005.

US20050137227
General References
  1. Ginsburg AS, Hooper N, Parrish N, Dooley KE, Dorman SE, Booth J, Diener-West M, Merz WG, Bishai WR, Sterling TR: Fluoroquinolone resistance in patients with newly diagnosed tuberculosis. Clin Infect Dis. 2003 Dec 1;37(11):1448-52. Epub 2003 Nov 4. [PubMed:14614666]
External Links
Human Metabolome Database
HMDB0014363
KEGG Drug
D08237
KEGG Compound
C07663
PubChem Compound
152946
PubChem Substance
46508509
ChemSpider
134802
BindingDB
50366824
ChEBI
63611
ChEMBL
CHEMBL32
Therapeutic Targets Database
DAP000158
PharmGKB
PA450555
HET
MFX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Moxifloxacin
ATC Codes
J01MA14 — MoxifloxacinS01AE07 — Moxifloxacin
AHFS Codes
  • 52:04.04 — Antibacterials
  • 08:12.18 — Quinolones
PDB Entries
2xkk / 3fof / 4z2c / 4z3o / 5bs8 / 5bta / 5cdq
FDA label
Download (162 KB)
MSDS
Download (193 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1Active Not RecruitingBasic ScienceCoronary Artery Disease1
1Active Not RecruitingBasic ScienceElectrocardiogram Repolarisation Abnormality / Gonococcal infections / Gonorrhoea1
1Active Not RecruitingDiagnosticHealthy Volunteers1
1Active Not RecruitingTreatmentCardiovascular Disease (CVD) / Heart Failure, Unspecified / Pulmonary Arterial Hypertension (PAH)1
1Active Not RecruitingTreatmentCongestive Heart Failure (CHF)1
1CompletedNot AvailableAlzheimer's Disease (AD)1
1CompletedNot AvailableCardiac Repolarization / Healthy Volunteers1
1CompletedNot AvailableCardiodynamics / Pharmacokinetics / Safety / Tolerability1
1CompletedNot AvailableClinical Pharmacology, Healthy Volunteer Study1
1CompletedNot AvailableContraception1
1CompletedNot AvailableFunctional Dyspepsia1
1CompletedNot AvailableHealthy Volunteers13
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of Isavuconazole1
1CompletedNot AvailableHeart Repolarization1
1CompletedNot AvailableHepatitis C Viral Infection1
1CompletedNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedNot AvailableLice Infestations1
1CompletedNot AvailableQt Interval, Variation in1
1CompletedBasic ScienceAlzheimer's Disease (AD)1
1CompletedBasic ScienceAmount of NKTR-118 in Blood / Variation in the Heart's Electrical Cycle1
1CompletedBasic ScienceAsthma Bronchial1
1CompletedBasic ScienceBacterial Infections1
1CompletedBasic ScienceC-Peptide Effects on the QT/QTc Interval / Effects of Different Meals on the QT/QTc Interval / Insulin and Oral Hypoglycemic [Antidiabetic] Drugs Causing Adverse Effects in Therapeutic Use / Japanese vs. Caucasian TQT Comparison / Moxifloxacin ECG Profile in Fed and Fasted State1
1CompletedBasic ScienceChronic Lung Diseases / Chronic Obstructive Pulmonary Disease (COPD)1
1CompletedBasic ScienceDrug-induced QT Interval Prolongation / Pharmacodynamics / Pharmacokinetics1
1CompletedBasic ScienceEffects of Sativex on ECG1
1CompletedBasic ScienceFibromyalgia1
1CompletedBasic ScienceHealthy Male Volunteers1
1CompletedBasic ScienceHealthy Volunteers16
1CompletedBasic ScienceHealthy Volunteers / Type 2 Diabetes Mellitus1
1CompletedBasic ScienceInfection NOS1
1CompletedBasic ScienceMalignant Lymphomas / Refractory Solid Tumors1
1CompletedBasic SciencePharmacokinetics1
1CompletedBasic ScienceRestless Legs Syndrome (RLS)1
1CompletedBasic ScienceRheumatoid Arthritis1
1CompletedBasic ScienceSchizophrenic Disorders1
1CompletedBasic ScienceTTR Cardiomyopathy1
1CompletedBasic ScienceTumors, Solid1
1CompletedBasic ScienceType 2 Diabetes Mellitus1
1CompletedDiagnosticHealthy Volunteers1
1CompletedDiagnosticHuman Volunteers1
1CompletedDiagnosticTherapeutic Agent Toxicity1
1CompletedDiagnosticThe Effect of Moxifloxacin on QT/QTc Interval1
1CompletedEducational/Counseling/TrainingPatients With Pace Makers But no Evidence of Ischemic Heart Disease1
1CompletedOtherCardiovascular Abnormalities1
1CompletedOtherChemotherapy-Induced Nausea and Vomiting (CINV) / Nausea and Vomiting, Postoperative1
1CompletedOtherHealthy Volunteers9
1CompletedOtherMalaria caused by plasmodium vivax1
1CompletedOtherTuberculosis Infection1
1CompletedPreventionHealthy Volunteers3
1CompletedScreeningCataract Extraction1
1CompletedScreeningHealthy Volunteers1
1CompletedTreatmentAcute Coronary Syndromes (ACS)1
1CompletedTreatmentAlzheimer's Disease (AD) / Healthy Volunteers1
1CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1CompletedTreatmentAnemias2
1CompletedTreatmentAsthma Bronchial1
1CompletedTreatmentCancer, Breast1
1CompletedTreatmentCardiac Conduction and Repolarization1
1CompletedTreatmentCardiac Effects in Normal Healthy Volunteers1
1CompletedTreatmentCardiac Repolarization in Healthy Subjects2
1CompletedTreatmentCardiac Repolarization / Healthy Volunteers1
1CompletedTreatmentChronic Lung Diseases / Moxifloxacin / Pulmonary Diseases1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Healthy Volunteers1
1CompletedTreatmentCystic Fibrosis (CF)1
1CompletedTreatmentDiabetes Mellitus (DM) / Healthy Volunteers1
1CompletedTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus1
1CompletedTreatmentDyslipidemias2
1CompletedTreatmentECG Effects1
1CompletedTreatmentElectrocardiography / QTc Evaluation1
1CompletedTreatmentEpilepsies1
1CompletedTreatmentErectile Dysfunction (ED)1
1CompletedTreatmentHealthy Adult Male and Female Volunteers1
1CompletedTreatmentHealthy Participants / Systemic Lupus Erythematosus (SLE)1
1CompletedTreatmentHealthy Volunteers53
1CompletedTreatmentHepatitis C Viral Infection2
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentHuman Experimentation (Human Volunteers)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentNormal Healthy Subjects1
1CompletedTreatmentObstetric Labour, Premature1
1CompletedTreatmentOccasional Constipation1
1CompletedTreatmentParkinson's Disease (PD)2
1CompletedTreatmentPhenylketonuria (PKU)1
1CompletedTreatmentPostoperative pain1
1CompletedTreatmentPulmonary Disease, Chronic Obstructive1
1CompletedTreatmentQT Interval1
1CompletedTreatmentQTc Interval1
1CompletedTreatmentQt Interval, Variation in1
1CompletedTreatmentRenal Cell Adenocarcinoma / Tumors, Solid1
1CompletedTreatmentRespiratory Tract Infections (RTI)1
1CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
1CompletedTreatmentSchizophrenic Disorders1
1CompletedTreatmentTuberculosis Infection1
1CompletedTreatmentTumors, Solid1
1Not Yet RecruitingBasic ScienceDiabetes Mellitus (DM)1
1RecruitingBasic ScienceHealthy Volunteers1
1RecruitingOtherHealthy Volunteers1
1RecruitingTreatmentDyslipidemias1
1RecruitingTreatmentHealthy Volunteers2
1TerminatedBasic ScienceHealthy Males1
1TerminatedOtherHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
1TerminatedTreatmentMycobacterium Tuberculosis1
1Unknown StatusTreatmentCardiac Toxicity1
1WithdrawnTreatmentAlzheimer's Disease (AD)1
1WithdrawnTreatmentAsthma Bronchial1
1WithdrawnTreatmentBacterial Infections2
1WithdrawnTreatmentTuberculosis Infection1
1, 2CompletedPreventionRecurrent Tuberculosis1
1, 2CompletedTreatmentMulti-Drug Resistant Tuberculosis / Tuberculosis Infection1
2CompletedNot AvailableMalignancies / Tumors, Solid1
2CompletedBasic ScienceHealthy Volunteers1
2CompletedBasic ScienceTuberculosis Infection1
2CompletedPreventionEndophthalmitis1
2CompletedTreatmentAcute Otitis Media1
2CompletedTreatmentAdvanced Breast Cancer / Antibacterial Drug / Antibiotic / Stable Disease With a Trend of Progression / Treatment of Physician's Choice1
2CompletedTreatmentCholangitis1
2CompletedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP)1
2CompletedTreatmentConjunctivitis, Bacterial1
2CompletedTreatmentOff Episodes of Parkinson Disease / Parkinson's Disease (PD)1
2CompletedTreatmentPharmacodynamics / Pharmacokinetics / Tolerability / Tuberculous Meningitis1
2CompletedTreatmentPneumonia1
2CompletedTreatmentPulmonary Tuberculosis (TB)4
2CompletedTreatmentSpasticity1
2CompletedTreatmentTuberculosis Infection6
2RecruitingTreatmentDrug-resistant Tuberculosis / Extensively Drug Resistant Tuberculosis / Multi-Drug Resistant Tuberculosis / Pulmonary Tuberculosis (TB) / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
2TerminatedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP)1
2TerminatedTreatmentCorneal Infiltrates1
2TerminatedTreatmentOsteomyelitis1
2TerminatedTreatmentUlcerative keratitis1
2Unknown StatusTreatmentTuberculosis Infection1
2, 3Not Yet RecruitingPreventionEndophthalmitis1
2, 3RecruitingTreatmentExtensively Drug Resistant Tuberculosis / Pulmonary Tuberculosis (TB) / Tuberculosis, Multidrug Resistant1
2, 3RecruitingTreatmentExtensively Drug Resistant Tuberculosis / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
3CompletedPreventionBacteremia / Hodgkins Disease (HD) / Multiple Myeloma (MM) / Non-Hodgkin's Lymphoma (NHL)1
3CompletedPreventionChronic Bronchitis / Chronic Lung Diseases1
3CompletedTreatmentAbscesses / Diabetic Foot / Ulcers / Wound Infections1
3CompletedTreatmentAcute Bacterial Conjunctivitis1
3CompletedTreatmentAcute Calculous Cholecystitis1
3CompletedTreatmentAcute Otitis Externa1
3CompletedTreatmentAcute Otitis Media1
3CompletedTreatmentChronic Bronchitis1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentCommunity Acquired Bacterial Pneumonia / Community Acquired Pneumonia (CAP)1
3CompletedTreatmentCommunity Acquired Pneumonia (CAP)2
3CompletedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP)2
3CompletedTreatmentCommunity-Acquired Infections / Pneumonia, Bacterial1
3CompletedTreatmentConjunctivitis, Bacterial2
3CompletedTreatmentBacterial blepharitis / Conjunctivitis / Corneal Inflammation1
3CompletedTreatmentInfection NOS1
3CompletedTreatmentInfectious Diseases1
3CompletedTreatmentIntra-Abdominal Infections1
3CompletedTreatmentIntraabdominal Infections1
3CompletedTreatmentLung Abscess / Pneumonia, Aspiration1
3CompletedTreatmentPelvic Inflammatory Disease (PID)2
3CompletedTreatmentPneumonia2
3CompletedTreatmentPulmonary Multi-Drug Resistant Tuberculosis (MDR-TB) / Tuberculosis, Pulmonary, Drug Sensitive1
3CompletedTreatmentPulmonary Tuberculosis (TB)1
3CompletedTreatmentSevere Sepsis / Shock, Septic1
3CompletedTreatmentSinusitis1
3Not Yet RecruitingTreatmentCataract operation / Endophthalmitis / Intracameral Antibiotics / Moxifloxacin / Phacoemulsification / Vancomycin1
3RecruitingTreatmentAtypical; Mycobacterium, Pulmonary, Tuberculous1
3RecruitingTreatmentKeratitis; Infectious Disease (Manifestation)1
3RecruitingTreatmentMulti-Drug Resistant Tuberculosis1
3RecruitingTreatmentTuberculosis Infection2
3RecruitingTreatmentTuberculosis, Multidrug Resistant1
3TerminatedPreventionEndophthalmitis1
3TerminatedSupportive CareCancer of the Ovary / Cancer, Breast / Chronic Myeloproliferative Disorders / Gestational Trophoblastic Disease / Infection NOS / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms / Neuroblastomas / Testicular germ cell tumour1
3TerminatedTreatmentAcute Otitis Media1
3TerminatedTreatmentSkin Diseases, Infectious1
3TerminatedTreatmentTuberculosis Infection1
3Unknown StatusNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
3Unknown StatusPreventionEye Infections1
3Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastritis Chronic1
3Unknown StatusTreatmentCellulitis1
3WithdrawnTreatmentSkin Structures and Soft Tissue Infections1
4CompletedNot AvailableAbscesses / Cysts1
4CompletedNot AvailableCataract operation1
4CompletedNot AvailableCataract operation / Corneal Health1
4CompletedNot AvailableConjunctivitis, Bacterial1
4CompletedBasic ScienceAnti-Biotic Resistance1
4CompletedBasic ScienceCataracts1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedBasic ScienceSide-effect of Antibiotic1
4CompletedOtherCataract Extraction1
4CompletedOtherHealthy Volunteers1
4CompletedPreventionCataracts1
4CompletedSupportive CareBacterial Infections / Cataract Extraction / Eye Infections1
4CompletedSupportive CareBacterial Infections / Eye Infections2
4CompletedSupportive CareGeneralized Aggressive Periodontitis / Periodontitis, Aggressive1
4CompletedTreatmentBody Weights / Bypass, Gastric1
4CompletedTreatmentCataract Extraction1
4CompletedTreatmentCataracts1
4CompletedTreatmentChronic Bronchitis1
4CompletedTreatmentChronic Generalized Periodontitis1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedTreatmentConjunctivitis1
4CompletedTreatmentConjunctivitis, Bacterial2
4CompletedTreatmentElectrocardiogram QTc interval prolonged1
4CompletedTreatmentEye Infections, Bacterial / Ulcerative keratitis1
4CompletedTreatmentHelicobacter Infections1
4CompletedTreatmentIntra-Abdominal Infections1
4CompletedTreatmentMaxillary Sinusitis1
4CompletedTreatmentPelvic Inflammatory Disease (PID)1
4CompletedTreatmentPeriodontitis, Chronic1
4CompletedTreatmentPneumonia1
4CompletedTreatmentHepatic abscess1
4Enrolling by InvitationPreventionCardiac Dysrhythmia1
4Not Yet RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
4RecruitingPreventionCataracts / Endophthalmitis / Macula Edema1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedBasic ScienceTransplantation, Corneal1
4TerminatedTreatmentBacterial Infections / Sinusitis1
4TerminatedTreatmentCommunity Acquired Pneumonia (CAP)1
4TerminatedTreatmentTuberculosis Infection1
4Unknown StatusPreventionCataracts1
4Unknown StatusPreventionEye Infections / Infection NOS1
4Unknown StatusTreatmentCommunity Acquired Pneumonia (CAP)1
4Unknown StatusTreatmentIntravitreal Injection Patients1
4Unknown StatusTreatmentReinfection Pulmonary Tuberculosis1
Not AvailableActive Not RecruitingDiagnosticLong qt Syndrome1
Not AvailableCompletedNot AvailableAbscess, Intra-Abdominal / Secondary Peritonitis1
Not AvailableCompletedNot AvailableAcute Bacterial Sinusitis (ABS)1
Not AvailableCompletedNot AvailableAnti-Infective Agents1
Not AvailableCompletedNot AvailableBronchial Diseases / Chronic Bronchitis1
Not AvailableCompletedNot AvailableChronic Bronchitis2
Not AvailableCompletedNot AvailableChronic Bronchitis / Disease Exacerbation1
Not AvailableCompletedNot AvailableCorneal Epithelial Wound Healing1
Not AvailableCompletedNot AvailableDrug-Induced Liver Injury1
Not AvailableCompletedNot AvailablePneumonia1
Not AvailableCompletedNot AvailableSkin Diseases, Bacterial1
Not AvailableCompletedHealth Services ResearchHealthy Volunteers1
Not AvailableCompletedPreventionAge-Related Macular Degeneration (ARMD)1
Not AvailableCompletedPreventionInflammation Following Cataract Surgery1
Not AvailableCompletedPreventionPost Lasik Surgery Inflammation1
Not AvailableCompletedTreatmentEpithelium, Corneal1
Not AvailableCompletedTreatmentPeritoneal Dialysis Associated Peritonitis1
Not AvailableCompletedTreatmentPneumonia, Mycoplasma1
Not AvailableEnrolling by InvitationOtherAppendicitis Acute1
Not AvailableNot Yet RecruitingNot AvailableCommunity Acquired Pneumonia (CAP)1
Not AvailableRecruitingNot AvailableTuberculosis Infection1
Not AvailableRecruitingTreatmentAppendicitis Acute1
Not AvailableRecruitingTreatmentBronchiectasis1
Not AvailableRecruitingTreatmentDrug-resistant Tuberculosis / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
Not AvailableRecruitingTreatmentHelicobacter Infection2
Not AvailableTerminatedSupportive CareChronic Myeloproliferative Disorders / Fever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms / Neutropenias / Precancerous Conditions / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableUnknown StatusTreatmentProlongation of QT interval1
Not AvailableWithdrawnPreventionConjunctical Flora1

Pharmacoeconomics

Manufacturers
  • Bayer healthcare pharmaceuticals inc
  • Alcon inc
  • Bayer Healthcare Pharmaceuticals
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Alcon Laboratories
  • A-S Medication Solutions LLC
  • Bayer Healthcare
  • Cardinal Health
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Fresenius Kabi AB
  • H.J. Harkins Co. Inc.
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Redpharm Drug
  • Schering Corp.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
Dosage forms
FormRouteStrength
SolutionOphthalmic0.5 %
Injection, solutionIntravenous400 mg/250mL
TabletOral400 mg
Tablet, film coatedOral400 mg/1
SolutionIntravenous400 mg
Injection, solutionOphthalmic
Injection, solutionIntraocular
TabletOral400 mg/1
Injection, solutionIntraocular5 mg/1mL
Injection, solutionOphthalmic5 mg/1mL
Injection, suspensionOphthalmic
SuspensionOphthalmic
SolutionOphthalmic5 mg/1mL
Solution / dropsOphthalmic5 mg/1mL
Prices
Unit descriptionCostUnit
Vigamox 0.5% Solution 3ml Bottle90.72USD bottle
Vigamox 0.5% eye drops27.22USD ml
Avelox 400 mg tablet16.68USD tablet
Avelox abc pack 400 mg tablet16.35USD tablet
Avelox iv 400 mg/250 ml0.17USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4990517No1991-02-052011-12-08Us
CA2342211No2009-05-262019-09-29Canada
CA1340114No1998-11-032015-11-03Canada
US5849752No1998-12-152016-12-05Us
US6610327No2003-08-262019-10-29Us
US6548079No2003-04-152020-07-25Us
US7671070Yes2010-03-022020-03-29Us
US6716830Yes2004-04-062020-03-29Us
US8450311No2013-05-282029-05-29Us
US9114168No2015-08-252029-05-29Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)238-242 °CNot Available
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.168 mg/mLALOGPS
logP0.01ALOGPS
logP-0.5ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)5.69ChemAxon
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82.11 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.22 m3·mol-1ChemAxon
Polarizability41.24 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9794
Blood Brain Barrier-0.9597
Caco-2 permeable-0.6093
P-glycoprotein substrateSubstrate0.8607
P-glycoprotein inhibitor INon-inhibitor0.7564
P-glycoprotein inhibitor IINon-inhibitor0.7181
Renal organic cation transporterNon-inhibitor0.7318
CYP450 2C9 substrateNon-substrate0.8018
CYP450 2D6 substrateNon-substrate0.8247
CYP450 3A4 substrateNon-substrate0.5756
CYP450 1A2 substrateNon-inhibitor0.7417
CYP450 2C9 inhibitorNon-inhibitor0.7735
CYP450 2D6 inhibitorNon-inhibitor0.8359
CYP450 2C19 inhibitorNon-inhibitor0.7401
CYP450 3A4 inhibitorNon-inhibitor0.8811
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5536
Ames testAMES toxic0.6227
CarcinogenicityNon-carcinogens0.9038
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3267 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8092
hERG inhibition (predictor II)Non-inhibitor0.6461
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0176900000-5ca9cd234a2a93f05658
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0391000000-7a74ddcc516a82243c1a

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 / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyrrolopyridines / Pyridinecarboxylic acids / Methoxyanilines / Dialkylarylamines / Anisoles
show 15 more
Substituents
Quinoline-3-carboxylic acid / Fluoroquinolone / Aminoquinoline / Haloquinoline / Dihydroquinolone / Dihydroquinoline / Pyrrolopyridine / Pyridine carboxylic acid or derivatives / Pyridine carboxylic acid / Methoxyaniline
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether, cyclopropanes, quinolone antibiotic, fluoroquinolone antibiotic, quinolone, quinolinemonocarboxylic acid, pyrrolidinopiperidine (CHEBI:63611)

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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Perez-Vazquez M, Roman F, Aracil B, Canton R, Campos J: Laboratory detection of Haemophilus influenzae with decreased susceptibility to nalidixic acid, ciprofloxacin, levofloxacin, and moxifloxacin due to GyrA and ParC mutations. J Clin Microbiol. 2004 Mar;42(3):1185-91. [PubMed:15004073]
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. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Dridi L, Tankovic J, Burghoffer B, Barbut F, Petit JC: gyrA and gyrB mutations are implicated in cross-resistance to Ciprofloxacin and moxifloxacin in Clostridium difficile. Antimicrob Agents Chemother. 2002 Nov;46(11):3418-21. [PubMed:12384345]
Kind
Protein
Organism
Human
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Reuveni D, Halperin D, Shalit I, Priel E, Fabian I: Moxifloxacin enhances etoposide-induced cytotoxic, apoptotic and anti-topoisomerase II effects in a human colon carcinoma cell line. Int J Oncol. 2010 Aug;37(2):463-71. [PubMed:20596674]
  3. Wohlkonig A, Chan PF, Fosberry AP, Homes P, Huang J, Kranz M, Leydon VR, Miles TJ, Pearson ND, Perera RL, Shillings AJ, Gwynn MN, Bax BD: Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance. Nat Struct Mol Biol. 2010 Sep;17(9):1152-3. doi: 10.1038/nsmb.1892. Epub 2010 Aug 29. [PubMed:20802486]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
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. Zhou SF, Yang LP, Zhou ZW, Liu YH, Chan E: Insights into the substrate specificity, inhibitors, regulation, and polymorphisms and the clinical impact of human cytochrome P450 1A2. AAPS J. 2009 Sep;11(3):481-94. doi: 10.1208/s12248-009-9127-y. Epub 2009 Jul 10. [PubMed:19590965]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 09:05