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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24FN3O4
Molecular Weight 401.4314
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOXIFLOXACIN

SMILES

COC1=C(N2C[C@@H]3CCCN[C@@H]3C2)C(F)=CC4=C1N(C=C(C(O)=O)C4=O)C5CC5

InChI

InChIKey=FABPRXSRWADJSP-MEDUHNTESA-N
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

HIDE SMILES / InChI

Molecular Formula C21H24FN3O4
Molecular Weight 401.4314
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AVELOX
Curative
AVELOX
Curative
AVELOX

Cmax

ValueDoseCo-administeredAnalytePopulation
443.07 ng/ml
1 drop 4 times / day multiple, ocular
MOXIFLOXACIN aqueous humor
Homo sapiens
3.1 mg/L
400 mg single, oral
MOXIFLOXACIN plasma
Homo sapiens
4.5 mg/L
400 mg 1 times / day multiple, oral
MOXIFLOXACIN plasma
Homo sapiens
3.9 mg/L
400 mg single, intravenous
MOXIFLOXACIN plasma
Homo sapiens
4.2 mg/L
400 mg 1 times / day multiple, intravenous
MOXIFLOXACIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
36.1 mg × h/L
400 mg single, oral
MOXIFLOXACIN plasma
Homo sapiens
48 mg × h/L
400 mg 1 times / day multiple, oral
MOXIFLOXACIN plasma
Homo sapiens
39.3 mg × h/L
400 mg single, intravenous
MOXIFLOXACIN plasma
Homo sapiens
38 mg × h/L
400 mg 1 times / day multiple, intravenous
MOXIFLOXACIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.55 h
400 mg single, oral
MOXIFLOXACIN plasma
Homo sapiens
12.7 h
400 mg 1 times / day multiple, oral
MOXIFLOXACIN plasma
Homo sapiens
11.8 h
400 mg single, intravenous
MOXIFLOXACIN plasma
Homo sapiens
14.8 h
400 mg 1 times / day multiple, intravenous
MOXIFLOXACIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
60%
400 mg single, oral
MOXIFLOXACIN plasma
Homo sapiens
60%
400 mg single, intravenous
MOXIFLOXACIN plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
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.
Substance Class Chemical
Record UNII
U188XYD42P
Record Status Validated (UNII)
Record Version