U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24FN3O4.ClH.H2O
Molecular Weight 455.908
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOXIFLOXACIN HYDROCHLORIDE MONOHYDRATE

SMILES

O.Cl.[H][C@]12CN(C[C@@]1([H])NCCC2)C3=C(OC)C4=C(C=C3F)C(=O)C(=CN4C5CC5)C(O)=O

InChI

InChIKey=SKZIMSDWAIZNDD-WJMOHVQJSA-N
InChI=1S/C21H24FN3O4.ClH.H2O/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);1H;1H2/t11-,16+;;/m0../s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16337789 | https://www.ncbi.nlm.nih.gov/pubmed/20516287 | https://www.ncbi.nlm.nih.gov/pubmed/25801151 | https://www.ncbi.nlm.nih.gov/pubmed/11600361

Moxifloxacin is a synthetic antibacterial agent developed by Bayer AG (initially called BAY 12-8039) for oral and intravenous administration. Moxifloxacin, a fluoroquinolone, is available as the monohydrochloride salt of 1-cyclopropyl-7-[(S,S)-2,8diazabicyclo[4.3.0]non-8-yl]-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3 quinoline carboxylic acid. Moxifloxacin is marketed worldwide (as the hydrochloride) under the brand names Avelox, Avalox, and Avalon for oral treatment. In most countries, the drug is also available in the parenteral form for intravenous infusion. Moxifloxacin is also sold in an ophthalmic solution (eye drops) under the brand names Vigamox, and Moxeza for the treatment of conjunctivitis (pink eye). Its antibacterial spectrum includes enteric Gram-(−) rods (Escherichia coli, Proteus species, Klebsiella species), Haemophilus influenzae, atypical bacteria (Mycoplasma, Chlamydia, Legionella), and Streptococcus pneumoniae, and anaerobic bacteria. It differs from earlier antibacterials of the fluoroquinolone class such as levofloxacin and ciprofloxacin in having greater activity against Gram-positive bacteria and anaerobes.

CNS Activity

Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s061s062,021277s057s058lbl.pdf

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
800.0 nM [IC50]
9200.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AVELOX

Approved Use

INDICATIONS AND USAGE AVELOX is a fluoroquinolone antibacterial indicated for treating infections in adults 18 years of age and older caused by designated susceptible bacteria, in the conditions listed below: Community Acquired Pneumonia, Skin and Skin Structure Infections: Uncomplicated and Complicated, Complicated Intra-Abdominal Infections, Plague, Acute Bacterial Sinusitis, Acute Bacterial Exacerbation of Chronic Bronchitis, To reduce the development of drug-resistant bacteria and maintain the effectiveness of AVELOX and other antibacterial drugs. AVELOX should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria.

Launch Date

1999
Curative
AVELOX

Approved Use

INDICATIONS AND USAGE AVELOX is a fluoroquinolone antibacterial indicated for treating infections in adults 18 years of age and older caused by designated susceptible bacteria, in the conditions listed below: Community Acquired Pneumonia, Skin and Skin Structure Infections: Uncomplicated and Complicated, Complicated Intra-Abdominal Infections, Plague, Acute Bacterial Sinusitis, Acute Bacterial Exacerbation of Chronic Bronchitis, To reduce the development of drug-resistant bacteria and maintain the effectiveness of AVELOX and other antibacterial drugs. AVELOX should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria.

Launch Date

1999
Curative
AVELOX

Approved Use

INDICATIONS AND USAGE AVELOX is a fluoroquinolone antibacterial indicated for treating infections in adults 18 years of age and older caused by designated susceptible bacteria, in the conditions listed below: Community Acquired Pneumonia, Skin and Skin Structure Infections: Uncomplicated and Complicated, Complicated Intra-Abdominal Infections, Plague, Acute Bacterial Sinusitis, Acute Bacterial Exacerbation of Chronic Bronchitis, To reduce the development of drug-resistant bacteria and maintain the effectiveness of AVELOX and other antibacterial drugs. AVELOX should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria.

Launch Date

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.1 mg/L
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.2 mg/L
400 mg 1 times / day multiple, intravenous
dose: 400 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3.9 mg/L
400 mg single, intravenous
dose: 400 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.5 mg/L
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
443.07 ng/ml
1 drop 4 times / day multiple, ocular
dose: 1 drop
route of administration: ocular
experiment type: multiple
co-administered:
MOXIFLOXACIN aqueous humor
Homo sapiens
population: unhealthy
age:
sex:
food status:
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
36.1 mg × h/L
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
38 mg × h/L
400 mg 1 times / day multiple, intravenous
dose: 400 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
39.3 mg × h/L
400 mg single, intravenous
dose: 400 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
48 mg × h/L
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.55 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
14.8 h
400 mg 1 times / day multiple, intravenous
dose: 400 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
11.8 h
400 mg single, intravenous
dose: 400 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.7 h
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
60%
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
60%
400 mg single, intravenous
dose: 400 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MOXIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg 1 times / day multiple, oral
Higher than recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources: Page: p.5
healthy, 30±7
n = 7
Health Status: healthy
Age Group: 30±7
Sex: M
Population Size: 7
Sources: Page: p.5
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources: Page: p.2062
healthy, 33.6
n = 8
Health Status: healthy
Age Group: 33.6
Sex: M
Population Size: 8
Sources: Page: p.2062
400 mg 1 times / day multiple, intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.8.9
unhealthy, 50
Health Status: unhealthy
Condition: Bacterial infections
Age Group: 50
Sex: M+F
Sources: Page: p.8.9
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash
Sources: Page: p.8.9
400 mg 1 times / day multiple, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.8.9
unhealthy, 50
Health Status: unhealthy
Condition: Bacterial infections
Age Group: 50
Sex: M+F
Sources: Page: p.8.9
Disc. AE: Nausea, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Nausea (>0.3)
Diarrhea (>0.3)
Dizziness (>0.3)
Vomiting (>0.3)
Sources: Page: p.8.9
800 mg 1 times / day multiple, oral
Highest studied dose
Dose: 800 mg, 1 times / day
Route: oral
Route: multiple
Dose: 800 mg, 1 times / day
Sources: Page: p.7
unhealthy, 57.8
n = 5
Health Status: unhealthy
Condition: Chronic bronchitis
Age Group: 57.8
Sex: M+F
Population Size: 5
Sources: Page: p.7
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Co-administed with::
Linezolid, IV(600 mg q12h)
Sources: Page: p.1863
unhealthy, 59.6
n = 273
Health Status: unhealthy
Condition: Community-acquired bacterial pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 273
Sources: Page: p.1863
Disc. AE: Erythema, QT interval prolonged...
AEs leading to
discontinuation/dose reduction:
Erythema (0.37%)
QT interval prolonged (1%)
Angioedema (serious, 0.37%)
Sources: Page: p.1863
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Disc. AE: Tendinitis, Tendon rupture...
AEs leading to
discontinuation/dose reduction:
Tendinitis
Tendon rupture
Peripheral neuropathy
Central nervous system disorder NOS
Myasthenia gravis
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Rash Disc. AE
400 mg 1 times / day multiple, intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.8.9
unhealthy, 50
Health Status: unhealthy
Condition: Bacterial infections
Age Group: 50
Sex: M+F
Sources: Page: p.8.9
Diarrhea >0.3
Disc. AE
400 mg 1 times / day multiple, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.8.9
unhealthy, 50
Health Status: unhealthy
Condition: Bacterial infections
Age Group: 50
Sex: M+F
Sources: Page: p.8.9
Dizziness >0.3
Disc. AE
400 mg 1 times / day multiple, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.8.9
unhealthy, 50
Health Status: unhealthy
Condition: Bacterial infections
Age Group: 50
Sex: M+F
Sources: Page: p.8.9
Nausea >0.3
Disc. AE
400 mg 1 times / day multiple, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.8.9
unhealthy, 50
Health Status: unhealthy
Condition: Bacterial infections
Age Group: 50
Sex: M+F
Sources: Page: p.8.9
Vomiting >0.3
Disc. AE
400 mg 1 times / day multiple, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.8.9
unhealthy, 50
Health Status: unhealthy
Condition: Bacterial infections
Age Group: 50
Sex: M+F
Sources: Page: p.8.9
Erythema 0.37%
Disc. AE
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Co-administed with::
Linezolid, IV(600 mg q12h)
Sources: Page: p.1863
unhealthy, 59.6
n = 273
Health Status: unhealthy
Condition: Community-acquired bacterial pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 273
Sources: Page: p.1863
QT interval prolonged 1%
Disc. AE
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Co-administed with::
Linezolid, IV(600 mg q12h)
Sources: Page: p.1863
unhealthy, 59.6
n = 273
Health Status: unhealthy
Condition: Community-acquired bacterial pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 273
Sources: Page: p.1863
Angioedema serious, 0.37%
Disc. AE
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Co-administed with::
Linezolid, IV(600 mg q12h)
Sources: Page: p.1863
unhealthy, 59.6
n = 273
Health Status: unhealthy
Condition: Community-acquired bacterial pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 273
Sources: Page: p.1863
Central nervous system disorder NOS Disc. AE
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Myasthenia gravis Disc. AE
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Peripheral neuropathy Disc. AE
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Tendinitis Disc. AE
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Tendon rupture Disc. AE
400 mg 1 times / day multiple, oral|intravenous
Recommended
Dose: 400 mg, 1 times / day
Route: oral|intravenous
Route: multiple
Dose: 400 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
PubMed

PubMed

TitleDatePubMed
Moxifloxacin: a review of its clinical potential in the management of community-acquired respiratory tract infections.
2000 Jan
Intracellular targets of moxifloxacin: a comparison with other fluoroquinolones.
2000 May
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000 Oct
Evidence of different profiles of side effects and drug-drug interactions among the quinolones--the pharmacokinetic standpoint.
2001
Effect of calcium supplements on the oral bioavailability of moxifloxacin in healthy male volunteers.
2001
Treatment of Staphylococcus aureus endocarditis using moxifloxacin.
2001 Aug
Acute community-acquired pneumonia: current diagnosis and treatment.
2001 Jan
Activity of moxifloxacin by itself and in combination with ethambutol, rifabutin, and azithromycin in vitro and in vivo against Mycobacterium avium.
2001 Jan
The efficacy and safety of two oral moxifloxacin regimens compared to oral clarithromycin in the treatment of community-acquired pneumonia.
2001 Jul
A comparison of the bactericidal activity of quinolone antibiotics in a Mycobacterium fortuitum model.
2001 Jun
Pharmacodynamics of moxifloxacin, levofloxacin and sparfloxacin against Streptococcus pneumoniae.
2001 Jun
Antimicrobial activity of fluoroquinolone photodegradation products determined by parallel-line bioassay and high performance liquid chromatography.
2001 Mar
Adverse reactions to fluoroquinolones. an overview on mechanistic aspects.
2001 Mar
Moxifloxacin: clinical efficacy and safety.
2001 Mar 1
Clinical perspectives on new antimicrobials: focus on fluoroquinolones.
2001 Mar 15
Evaluation of the clinical microbiology profile of moxifloxacin.
2001 Mar 15
Profile of moxifloxacin drug interactions.
2001 Mar 15
Comparative in vitro activity of moxifloxacin by E-test against Streptococcus pyogenes.
2001 Mar 15
Penicillin-resistant streptococcus pneumoniae: review of moxifloxacin activity.
2001 Mar 15
Treatment outcomes in acute exacerbations of chronic bronchitis: comparison of macrolides and moxifloxacin from the patient perspective.
2001 Mar-Apr
Activity of moxifloxacin and twelve other antimicrobial agents against 216 clinical isolates of Streptococcus pneumoniae.
2001 Mar-Apr
The canine Purkinje fiber: an in vitro model system for acquired long QT syndrome and drug-induced arrhythmogenesis.
2001 May
Comparison of antimicrobial in vitro activities against Streptococcus pneumoniae independent of MIC susceptibility breakpoints using MIC frequency distribution curves, scattergrams and linear regression analyses.
2001 Nov
Pharmacokinetics and pharmacodynamics of fluoroquinolones.
2001 Oct
In vitro activity of moxifloxacin against common clinical bacterial isolates in Taiwan.
2001 Sep
The efficacy of moxifloxacin in acute exacerbations of chronic bronchitis: a Spanish physician and patient experience.
2001 Sep
Patents

Sample Use Guides

The dose of AVELOX is 400 mg (orally or as an intravenous infusion) once every 24 hours. The duration of therapy depends on the type of infection (5--21 days).
Route of Administration: Oral
In Vitro Use Guide
Phagocytosed bacteria were divided into four aliquots with different concentrations of the drug (0, 0.1, 1 and 10 MIC). At baseline and after 1, 2 and 4 h incubation, the number of viable bacteria was determined by a subculture technique. Moxifloxacin was active against all tested staphylococci with MICs of 0.063–2 mg/L.
Name Type Language
MOXIFLOXACIN HYDROCHLORIDE MONOHYDRATE
Common Name English
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 HYDRATE HYDROCHLORIDE
Common Name English
MOXIFLOXACIN HYDROCHLORIDE [IP]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID1049063
Created by admin on Fri Dec 15 16:39:44 GMT 2023 , Edited by admin on Fri Dec 15 16:39:44 GMT 2023
PRIMARY
DRUG BANK
DBSALT002560
Created by admin on Fri Dec 15 16:39:44 GMT 2023 , Edited by admin on Fri Dec 15 16:39:44 GMT 2023
PRIMARY
CAS
192927-63-2
Created by admin on Fri Dec 15 16:39:44 GMT 2023 , Edited by admin on Fri Dec 15 16:39:44 GMT 2023
PRIMARY
PUBCHEM
9890250
Created by admin on Fri Dec 15 16:39:44 GMT 2023 , Edited by admin on Fri Dec 15 16:39:44 GMT 2023
PRIMARY
FDA UNII
B8956S8609
Created by admin on Fri Dec 15 16:39:44 GMT 2023 , Edited by admin on Fri Dec 15 16:39:44 GMT 2023
PRIMARY
DAILYMED
B8956S8609
Created by admin on Fri Dec 15 16:39:44 GMT 2023 , Edited by admin on Fri Dec 15 16:39:44 GMT 2023
PRIMARY
RXCUI
1926505
Created by admin on Fri Dec 15 16:39:44 GMT 2023 , Edited by admin on Fri Dec 15 16:39:44 GMT 2023
PRIMARY