Moxifloxacin

Moxifloxacin is an antibiotic, used to treat

bacterial infections,[3] including
pneumonia, conjunctivitis, endocarditis,
tuberculosis, and sinusitis.[3][4] It can be
given by mouth, by injection into a vein,
and as an eye drop.[4]
 Moxifloxacin

Clinical data
Trade names Avelox, Vigamox,
Moxiflox, others
Other names Moxifloxacine; BAY
12-8039
AHFS/Drugs.com Monograph (https://w
ww.drugs.com/mono
graph/moxifloxacin-h
ydrochloride.html)
MedlinePlus a600002 (https://med
lineplus.gov/druginfo/
meds/a600002.html)
License data US FDA: Moxifloxacin
(https://www.accessd
ata.fda.gov/scripts/c
der/drugsatfda/index.
cfm?fuseaction=Sear
ch.SearchAction&Sear
chTerm=Moxifloxacin
&SearchType=BasicS
earch)
Pregnancy AU: B3
category
Routes of By mouth,
administration
intravenous, eye
drops
Drug class Antibiotic
(fluoroquinolone)
ATC code J01MA14 (WHO (http
s://www.whocc.no/at
c_ddd_index/?code=J
01MA14) ) S01AE07
(WHO (https://www.w
hocc.no/atc_ddd_inde
x/?code=S01AE07) )

Legal status
Legal status AU: S4 (Prescription
only)
US: ℞-only

Pharmacokinetic data
Bioavailability 86%[1]
Protein binding 47%[1]
Metabolism Glucuronide and
sulfate conjugation;
CYP450 system not
involved[2]
Elimination half-life 12.1 hours[1]
Excretion Urine, feces

Identifiers

IUPAC name
1-Cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]
nonan-8-yl]-6-fluoro-8-methoxy-4-oxoquinoli
ne-3-carboxylic acid
CAS Number 151096-09-2 (https://
commonchemistry.ca
s.org/detail?cas_rn=1
51096-09-2)   [yes]
PubChem CID 152946 (https://pubc
hem.ncbi.nlm.nih.go
v/compound/15294
6)
DrugBank DB00218 (https://ww
w.drugbank.ca/drugs/
DB00218)  

ChemSpider 134802 (https://www.

chemspider.com/Che
mical-Structure.13480
2.html)  

UNII U188XYD42P (https://

precision.fda.gov/unii
search/srs/unii/U188
XYD42P)
KEGG D08237 (https://www.
kegg.jp/entry/D0823
7)
as HCl: D00874 (http
s://www.kegg.jp/entr
y/D00874)
ChEMBL ChEMBL32 (https://w
ww.ebi.ac.uk/chembl
db/index.php/compo
und/inspect/ChEMBL
32)  

NIAID ChemDB 070017 (https://chem

db.niaid.nih.gov/Com
poundDetails.aspx?AI
DSNO=070017)
CompTox Dashboard DTXSID3048491 (http
(EPA)
s://comptox.epa.gov/
dashboard/chemical/
details/DTXSID30484
91)
ECHA InfoCard 100.129.459 (https://
echa.europa.eu/subst
ance-information/-/su
bstanceinfo/100.129.
459)

Chemical and physical data

Formula C21H24FN3O4
Molar mass 401.438 g·mol−1
3D model (JSmol) Interactive image (htt
ps://chemapps.stolaf.
edu/jmol/jmol.php?m
 odel=COc1c2c%28c
c%28c1N3C%5BC%4
0%40H%5D4CCCN%5
BC%40%40H%5D4C
3%29F%29c%28%3D
O%29c%28cn2C5CC
5%29C%28%3DO%29
O)

SMILES
COc1c2c(cc(c1N3C[C@@H]4CCCN[C@@H]4
C3)F)c(=O)c(cn2C5CC5)C(=O)O
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,27,2
8)/t11-,16+/m0/s1 
Key:FABPRXSRWADJSP-MEDUHNTESA-N 
   (verify) (https://en.wikipedia.org/w/index.ph
p?title=Special:ComparePages&rev1=462255
811&page2=Moxifloxacin)

Common side effects include diarrhea,

dizziness, and headache.[3] Severe side
effects may include spontaneous tendon
ruptures, nerve damage, and worsening of
myasthenia gravis.[3] Safety of use in
pregnancy and breastfeeding is unclear.[5]
Moxifloxacin is in the fluoroquinolone
family of medications.[3] It usually kills
bacteria by blocking their ability to
duplicate DNA.[3]
Moxifloxacin was patented in 1988 and
approved for use in the United States in
1999.[6][7] It is on the World Health
Organization's List of Essential
Medicines.[8]

Medical uses
Moxifloxacin treats a number of infections,
including respiratory-tract infections,
cellulitis, anthrax, intra-abdominal
infections, endocarditis, meningitis, and
tuberculosis.[9]

In the United States, moxifloxacin is

licensed for the treatment of acute
bacterial sinusitis, acute bacterial
exacerbation of chronic bronchitis,
community-acquired pneumonia,
complicated and uncomplicated infections
of the skin and of the skin structure, and
complicated intra-abdominal infections.[10]
In the European Union, it is licensed for
acute bacterial exacerbations of chronic
bronchitis, non-severe community-
acquired pneumonia, and acute bacterial
sinusitis. On the basis of its investigation
into reports of rare but severe cases of
liver toxicity and skin reactions, the
European Medicines Agency
recommended in 2008 that the use of the
oral (but not the intravenous) form of
moxifloxacin be restricted to infections in
which other antibacterial agents cannot be
used or have failed.[11] In the United
States, the marketing approval does not
contain these restrictions, though the label
contains prominent warnings of skin
reactions.

The initial approval by the Food and Drug

Administration of the United States
(December 1999)[12] encompassed these
indications:

Acute exacerbations of chronic

bronchitis
Acute bacterial sinusitis
Community acquired pneumonia
Additional indications approved by the
Food and Drug Administration:

April 2001: Uncomplicated skin and

skin-structure infections[13]
May 2004: Community-acquired
pneumonia caused by multidrug-
resistant Streptococcus pneumoniae[14]
June 2005: Complicated skin and skin-
structure infections[15]
November 2005: Complicated intra-
abdominal infections[16]

The European Medicines Agency has

advised that, for pneumonia, acute
bacterial sinusitis, and acute
exacerbations of COPD, it should only be
used when other antibiotics are
inappropriate.[17][18]

Oral and intravenous moxifloxacin have

not been approved for children. Several
drugs in this class, including moxifloxacin,
are not licensed by the Food and Drug
Administration for use in children, because
of the risk of permanent injury to the
musculoskeletal system.[19][20][21]
Moxifloxacin eye drops are approved for
conjunctival infections caused by
susceptible bacteria.[22]
Recently, alarming reports of moxifloxacin
resistance rates among anaerobes have
been published. In Austria 36% of
Bacteroides have been reported to be
reistant to moxifloxacin,[23] while in Italy
resistance rates as high as 41% have been
reported.[24]

Susceptible bacteria

A broad spectrum of bacteria is

susceptible, including the following:

Staphylococcus aureus
Staphylococcus epidermidis
Streptococcus pneumoniae
 Haemophilus influenzae
Klebsiella spp.
Moraxella catarrhalis
Enterobacter spp.
Mycobacterium spp.
Bacillus anthracis
Mycoplasma genitalium[25]

Adverse effects
Rare but serious adverse effects that may
occur as a result of moxifloxacin therapy
include irreversible peripheral neuropathy,
spontaneous tendon rupture and
tendonitis,[26] hepatitis, psychiatric effects
(hallucinations, depression), torsades de
pointes, Stevens–Johnson syndrome and
Clostridium difficile-associated disease,[27]
and photosensitivity/phototoxicity
reactions.[28][29]

Several reports suggest the use of

moxifloxacin may lead to uveitis.[30]

Pregnancy and breastfeeding

Exposure of the developing fetus to

quinolones, including levofloxacin, during
the first-trimester is not associated with an
increased risk of stillbirths, premature
births, birth defects, or low birth weight.[31]
There is limited data about the appearance
of moxifloxacin in human breastmilk.
Animal studies have found that
moxifloxacin appears in significant
concentration in breastmilk.[32] Decisions
as to whether to continue therapy during
pregnancy or while breast feeding should
take the potential risk of harm to the fetus
or child into account, as well as the
importance of the drug to the well-being of
the mother.[33]

Contraindications
Only two listed contraindications are found
within the 2008 package insert:
"Nonsteroidal anti-inflammatory drugs
(NSAIDs): Although not observed with
moxifloxacin in preclinical and clinical
trials, the concomitant administration of
a nonsteroidal anti-inflammatory drug
with a fluoroquinolone may increase the
risks of CNS stimulation and
convulsions."[34]
"Moxifloxacin is contraindicated in
persons with a history of
hypersensitivity to moxifloxacin, any
member of the quinolone class of
antimicrobial agents, or any of the
product components."[34]
Though not stated as such within the
package insert, ziprasidone is also
considered to be contraindicated, as it
may have the potential to prolong QT
interval. Moxifloxacin should also be
avoided in patients with uncorrected
hypokalemia, or concurrent administration
of other medications known to prolong the
QT interval (antipsychotics and tricyclic
antidepressants).[35]

Moxifloxacin should be used with caution

in patients with diabetes, as glucose
regulation may be significantly altered.[35]
Moxifloxacin is also considered to be
contraindicated within the pediatric
population, pregnancy, nursing mothers,
patients with a history of tendon disorder,
patients with documented QT
prolongation,[36] and patients with epilepsy
or other seizure disorders.
Coadministration of moxifloxacin with
other drugs that also prolong the QT
interval or induce bradycardia (e.g., beta-
blockers, amiodarone) should be avoided.
Careful consideration should be given in
the use of moxifloxacin in patients with
cardiovascular disease, including those
with conduction abnormalities.[35]
Children and adolescents

The safety of moxifloxacin in human

patients under age 18 has not been
established. Animal studies suggest a risk
of musculoskeletal harm in juveniles.[33]

Interactions
Moxifloxacin is not believed to be
associated with clinically significant drug
interactions due to inhibition or
stimulation of hepatic metabolism. Thus, it
should not, for the most part, require
special clinical or laboratory monitoring to
ensure its safety.[37] Moxifloxacin has a
potential for a serious drug interaction
with NSAIDs.[38]

The combination of corticosteroids and

moxifloxacin has increased potential to
result in tendonitis and disability.[39]

Antacids containing aluminium or

magnesium ions inhibit the absorption of
moxifloxacin. Drugs that prolong the QT
interval (e.g., pimozide) may have an
additive effect on QT prolongation and
lead to increased risk of ventricular
arrhythmias. The international normalised
ratio may be increased or decreased in
patients treated with warfarin.[38]
Overdose
"In the event of acute overdose, the
stomach should be emptied and adequate
hydration maintained. ECG monitoring is
recommended due to the possibility of QT
interval prolongation. The patient should
be carefully observed and given supportive
treatment. The administration of activated
charcoal as soon as possible after oral
overdose may prevent excessive increase
of systemic moxifloxacin exposure. About
3% and 9% of the dose of moxifloxacin, as
well as about 2% and 4.5% of its
glucuronide metabolite are removed by
continuous ambulatory peritoneal dialysis
and hemodialysis, respectively." (Quoting
from 29 December 2008 package insert
for Avelox)[34]

Pharmacology

Mechanism of action

Moxifloxacin is a broad-spectrum
antibiotic that is active against both Gram-
positive and Gram-negative bacteria. It
functions by inhibiting DNA gyrase, a type
II topoisomerase, and topoisomerase IV,[40]
enzymes necessary to separate bacterial
DNA, thereby inhibiting cell replication.
Pharmacokinetics

About 52% of an oral or intravenous dose

of moxifloxacin is metabolized via
glucuronide and sulfate conjugation. The
cytochrome P450 system is not involved in
moxifloxacin metabolism, and is not
affected by moxifloxacin.[2] The sulfate
conjugate (M1) accounts for around 38%
of the dose, and is eliminated primarily in
the feces. Approximately 14% of an oral or
intravenous dose is converted to a
glucuronide conjugate (M2), which is
excreted exclusively in the urine. Peak
plasma concentrations of M2 are about
40% those of the parent drug, while
plasma concentrations of M1 are, in
general, less than 10% those of
moxifloxacin.[34]

In vitro studies with cytochrome (CYP)

P450 enzymes indicate that moxifloxacin
does not inhibit 80 CYP3A4, CYP2D6,
CYP2C9, CYP2C19, or CYP1A2, suggesting
that moxifloxacin is unlikely to alter the
pharmacokinetics of drugs metabolized by
these enzymes.[34][2]

The pharmacokinetics of moxifloxacin in

pediatric subjects have not been
studied.[34]
The elimination half-life of moxifloxacin is
11.5 to 15.6 hours (single-dose, oral).[41]
About 45% of an oral or intravenous dose
of moxifloxacin is excreted as unchanged
drug (about 20% in urine and 25% in
feces). A total of 96 ± 4% of an oral dose is
excreted as either unchanged drug or
known metabolites. The mean (± SD)
apparent total body clearance and renal
clearance are 12 ± 2 L/h and 2.6 ± 0.5 L/h,
respectively.[41] The CSF penetration of
moxifloxacin is 70% to 80% in patients
with meningitis.[42]
Chemistry
Moxifloxacin monohydrochloride is a
slightly yellow to yellow crystalline
substance.[34] It is synthesized in several
steps, the first involving the preparation of
racemic 2,8-diazabicyclo[4.3.0]nonane
which is then resolved using tartaric acid.
A suitably derivatised quinolinecarboxylic
acid is then introduced, in the presence of
DABCO, followed by acidification to form
moxifloxacin hydrochloride.[43]
History
Moxifloxacin was first patented (United
States patent) in 1991 by Bayer A.G., and
again in 1997.[44] Avelox was subsequently
approved by the U.S. Food and Drug
Administration (FDA) for use in the United
States in 1999 to treat specific bacterial
infections.[6] Ranking 140th within the top
200 prescribed drugs in the United States
for 2007,[45] Avelox generated sales of
$697.3 million worldwide.[46]

Moxifloxacin is also manufactured by

Alcon as Vigamox.[47]
Patent

A United States patent application was

made on 30 June 1989, for Avelox, Bayer
A.G. being the assignee, which was
subsequently approved on 5 February
1991. This patent was scheduled to expire
on 30 June 2009. However, this patent
was extended for an additional two and
one half years on 16 September 2004, and
as such was not expected to expire until
2012.[48] Moxifloxacin was subsequently
(ten years later) approved by the FDA for
use in the United States in 1999. At least
four additional United States patents have
been filed regarding moxifloxacin
hydrochloride since the 1989 United
States application,[44][49] as well as patents
outside of the US.

Society and culture

Regulatory actions

Regulatory agencies have taken actions to

address certain rare but serious adverse
events associated with moxifloxacin
therapy.

Based on its investigation into reports of

rare but severe cases of liver toxicity and
skin reactions, the European Medicines
Agency recommended in 2008 that the
use of the oral (but not the IV) form of
moxifloxacin be restricted to infections in
which other antibacterial agents cannot be
used or have failed.[11] Similarly, the
Canadian label includes a warning of the
risk of liver injury.[50]

The U.S. label does not contain

restrictions similar to the European label,
but a carries a "black box" warning of the
risk of tendon damage and/or rupture and
warnings regarding the risk of irreversible
peripheral neuropathy.[51]
Generic equivalents

In 2007, the U.S. District Court for the

District of Delaware held that two Bayer
patents on Avelox are valid and
enforceable, and infringed by Dr. Reddy's
ANDA for a generic version of
Avelox.[52][53] The district court sided with
Bayer, citing the Federal Circuit's prior
decision in Takeda v. Alphapharm[54] as
"affirming the district court's finding that
defendant failed to prove a prima facie
case of obviousness where the prior art
disclosed a broad selection of
compounds, any one of which could have
been selected as a lead compound for
further investigation, and defendant did
not prove that the prior art would have led
to the selection of the particular
compound singled out by defendant."
According to Bayer's press release[52]
announcing the court's decision, it was
noted that Teva had also challenged the
validity of the same Bayer patents at issue
in the Dr. Reddy's case. Within Bayer's first-
quarter 2008 stockholder's newsletter[55]
Bayer stated that they had reached an
agreement with Teva Pharmaceuticals
USA, Inc., the adverse party, to settle their
patent litigation with regard to the two
Bayer patents. Under the settlement terms
agreed upon, Teva would obtain a license
to sell its generic moxifloxacin tablet
product in the U.S. shortly before the
second of the two Bayer patents expires in
March 2014. In Bangladesh, it is available
with brand name of Optimox.

References
1. Zhanel GG, Fontaine S, Adam H, Schurek
K, Mayer M, Noreddin AM, et al. (2006). "A
Review of New Fluoroquinolones : Focus
on their Use in Respiratory Tract
Infections". Treatments in Respiratory
Medicine. 5 (6): 437–465.
doi:10.2165/00151829-200605060-00009
(https://doi.org/10.2165%2F00151829-20
0605060-00009) . PMID 17154673 (http
s://pubmed.ncbi.nlm.nih.gov/17154673) .
 S2CID 26955572 (https://api.semanticsch
olar.org/CorpusID:26955572) .
2. World Health Organization (2008).
Guidelines for the Programmatic
Management of Drug-resistant
Tuberculosis (https://books.google.com/b
ooks?id=XKsLsl4_v4QC&pg=PA189) .
World Health Organization. pp. 189–.
ISBN 978-92-4-154758-1.
3. "Moxifloxacin Hydrochloride" (https://ww
w.drugs.com/monograph/moxifloxacin-hy
drochloride.html) . The American Society
of Health-System Pharmacists. Retrieved
29 August 2017.
4. British national formulary : BNF 69
(69 ed.). British Medical Association.
2015. pp. 408, 757. ISBN 9780857111562.
5. "Moxifloxacin Use During Pregnancy" (http
s://www.drugs.com/pregnancy/moxifloxa
cin.html) . Drugs.com. Retrieved
10 December 2017.
6. "Details for NDA:021085" (http://www.dru
gpatentwatch.com/p/NDA/021085) .
DrugPatentWatch. Retrieved 17 July 2009.
7. Fischer J, Ganellin CR (2006). Analogue-
based Drug Discovery (https://books.goog
le.com/books?id=FjKfqkaKkAAC&pg=PA5
01) . John Wiley & Sons. p. 501.
ISBN 9783527607495.
 8. World Health Organization (2019). World
Health Organization model list of essential
medicines: 21st list 2019. Geneva: World
Health Organization. hdl:10665/325771 (h
ttps://hdl.handle.net/10665%2F325771) .
WHO/MVP/EMP/IAU/2019.06. License:
CC BY-NC-SA 3.0 IGO.
9. "Avelox" (https://www.drugs.com/monogr
aph/avelox.html) . The American Society
of Health-System Pharmacists. Retrieved
3 April 2011.
10. "Documents" (http://www.accessdata.fda.
gov/drugsatfda_docs/label/2012/021085
s55-021277s052lbl.pdf) (PDF).
accessdata.fda.gov.
11. "Press release" (http://www.emea.europa.
eu/docs/en_GB/documednt_library/Press
_release/2010/08/WC500095423.pdf)
(PDF). Europa (web portal).

12. "Application letter" (http://www.accessdat

a.fda.gov/drugsatfda_docs/appletter/199
9/21085ltr.pdf) (PDF).
accessdata.fda.gov. 1999. Retrieved
7 June 2019.
13. "Approval of supplements" (http://www.ac
cessdata.fda.gov/drugsatfda_docs/nda/2
001/21-085S010_Avelox_Approv.pdf)
(PDF). accessdata.fda.gov. 2001.
Retrieved 7 June 2019.
14. "Application letter" (http://www.accessdat
a.fda.gov/drugsatfda_docs/appletter/200
4/21085se1-022,21277se1-017ltr.pdf)
(PDF). accessdata.fda.gov. 2004.
Retrieved 7 June 2019.
15. "Approval of supplements" (http://www.ac
cessdata.fda.gov/drugsatfda_docs/applet
ter/2005/021085s026,021277s022ltr.pd
f) (PDF). accessdata.fda.gov. 2005.
Retrieved 7 June 2019.
16. "Application letter" (http://www.accessdat
a.fda.gov/drugsatfda_docs/appletter/200
5/021085s027,029,021277s024,025ltr.pd
f) (PDF). accessdata.fda.gov. Retrieved
7 June 2019.
17. "Moxifloxacin: increased risk of life-
threatening liver reactions and other
serious risks" (https://www.gov.uk/drug-s
afety-update/moxifloxacin-increased-risk-
of-life-threatening-liver-reactions-and-othe
r-serious-risks) . gov.uk. Retrieved
8 February 2022.
18. "European Medicines Agency
recommends restricting the use of oral
moxifloxacin-containing medicines" (http
s://web.archive.org/web/2009070812502
0/http://www.emea.europa.eu/pdfs/huma
n/press/pr/38292708en.pdf) (PDF).
European Medicines Agency. 24 July
2008. Archived from the original (http://w
ww.emea.europa.eu/pdfs/human/press/p
r/38292708en.pdf) (PDF) on 8 July 2009.
Retrieved 20 July 2009.
19. "SYNOPSIS" (http://download.veritasmedi
cine.com/PDF/CR002392_CSR.pdf)
(PDF). Retrieved 29 January 2009.
20. Karande SC, Kshirsagar NA (February
1992). "Adverse drug reaction monitoring
of ciprofloxacin in pediatric practice".
Indian Pediatrics. 29 (2): 181–188.
PMID 1592498 (https://pubmed.ncbi.nlm.
nih.gov/1592498) .
21. Dolui SK, Das M, Hazra A (2007).
"Ofloxacin-induced reversible arthropathy
in a child" (https://doi.org/10.4103%2F002
2-3859.32220) . Journal of Postgraduate
Medicine. 53 (2): 144–145.
doi:10.4103/0022-3859.32220 (https://do
i.org/10.4103%2F0022-3859.32220) .
PMID 17495385 (https://pubmed.ncbi.nl
m.nih.gov/17495385) .
22. "Center for drug evaluation and research
Application number 21-598" (http://www.a
ccessdata.fda.gov/drugsatfda_docs/nda/
2003/21-598_Vigamox_approv.PDF)
(PDF). Food and Drug Administration
(FDA). 15 April 2005. Retrieved 21 July
2009.
23. König E, Ziegler HP, Tribus J, Grisold AJ,
Feierl G, Leitner E (April 2021).
"Surveillance of Antimicrobial
Susceptibility of Anaerobe Clinical
Isolates in Southeast Austria: Bacteroides
fragilis Group Is on the Fast Track to
Resistance" (https://www.ncbi.nlm.nih.go
v/pmc/articles/PMC8143075) .
Antibiotics. 10 (5): 479.
doi:10.3390/antibiotics10050479 (https://
doi.org/10.3390%2Fantibiotics1005047
9) . PMC 8143075 (https://www.ncbi.nlm.
nih.gov/pmc/articles/PMC8143075) .
PMID 33919239 (https://pubmed.ncbi.nl
m.nih.gov/33919239) .
24. Principe L, Sanson G, Luzzati R,
Aschbacher R, Pagani E, Luzzaro F, Di
Bella S (August 2022). "Time to reconsider
moxifloxacin anti-anaerobic activity?".
Journal of Chemotherapy: 1–2.
doi:10.1080/1120009X.2022.2106637 (htt
ps://doi.org/10.1080%2F1120009X.2022.
2106637) . PMID 35947127 (https://pubm
ed.ncbi.nlm.nih.gov/35947127) .
S2CID 251470489 (https://api.semanticsc
holar.org/CorpusID:251470489) .
25. Unemo M, Jensen JS (March 2017).
"Antimicrobial-resistant sexually
transmitted infections: gonorrhoea and
Mycoplasma genitalium". Nature Reviews.
Urology. 14 (3): 139–152.
doi:10.1038/nrurol.2016.268 (https://doi.o
rg/10.1038%2Fnrurol.2016.268) .
PMID 28072403 (https://pubmed.ncbi.nl
m.nih.gov/28072403) . S2CID 205521926
(https://api.semanticscholar.org/CorpusI
D:205521926) .
26. Albrecht R (28 July 2004). "NDA 21-085/S-
024, NDA 21-277/S-019" (http://www.acce
ssdata.fda.gov/drugsatfda_docs/applette
r/2004/21277s019,21085s024ltr.pdf)
(PDF). Center for Drug Evaluation and
Research. Food and Drug Administration
(FDA). Retrieved 31 July 2009.
27. Albrecht R (31 May 2007). "NDA 21-085/S-
036, NDA 21-277/S-030" (http://www.acce
ssdata.fda.gov/drugsatfda_docs/applette
r/2007/021085s036,021277s030ltr.pdf)
(PDF). Center for Drug Evaluation and
Research. Food and Drug Administration
(FDA). Retrieved 31 July 2009.
28. Albrecht R (15 February 2008). "NDA 21-
085/S-038, NDA 21-277/S-031" (http://ww
w.accessdata.fda.gov/drugsatfda_docs/a
ppletter/2008/021085s038ltr.pdf) (PDF).
Division of Special Pathogen and
Transplant Products. Food and Drug
Administration (FDA). Retrieved 31 July
2009.
29. DEPARTMENT OF HEALTH & HUMAN
SERVICES (28 February 2008). "NDA 21-
085/S-014, S-015, S-017" (http://www.acc
essdata.fda.gov/drugsatfda_docs/applett
er/2003/21085slr014se1-015slr017,2127
7slr006se1-007slr009ltr.pdf) (PDF). Food
and Drug Administration (FDA). Retrieved
17 July 2009.
30. "Risk for Uveitis With Oral Moxifloxacin" (h
ttp://archopht.jamanetwork.com/article.a
spx?articleid=1913582) . JAMA
Ophthalmology online. 2 October 2014.
31. Ziv A, Masarwa R, Perlman A, Ziv D, Matok
I (March 2018). "Pregnancy Outcomes
Following Exposure to Quinolone
Antibiotics - a Systematic-Review and
Meta-Analysis". Pharmaceutical Research.
35 (5): 109. doi:10.1007/s11095-018-
2383-8 (https://doi.org/10.1007%2Fs1109
5-018-2383-8) . PMID 29582196 (https://p
ubmed.ncbi.nlm.nih.gov/29582196) .
S2CID 4724821 (https://api.semanticscho
lar.org/CorpusID:4724821) .
32. Balfour JA, Lamb HM (January 2000).
"Moxifloxacin: a review of its clinical
potential in the management of
community-acquired respiratory tract
infections". Drugs. 59 (1): 115–139.
doi:10.2165/00003495-200059010-00010
(https://doi.org/10.2165%2F00003495-20
0059010-00010) . PMID 10718103 (http
s://pubmed.ncbi.nlm.nih.gov/10718103) .
33. "merck.com" (https://www.merck.com/pro
duct/usa/pi_circulars/a/avelox/avelox_pi.
pdf) (PDF).
34. Bayer (December 2008). "AVELOX
(moxifloxacin hydrochloride) Tablets
AVELOX I.V. (moxifloxacin hydrochloride in
sodium chloride injection)" (http://www.ac
cessdata.fda.gov/drugsatfda_docs/label/
2008/021085s039,021277s033lbl.pdf)
(PDF). Food and Drug Administration
(FDA). p. 19. Retrieved 2 November 2010.
35. "Moxifloxacin" (https://web.archive.org/we
b/20090307063002/http://www.umm.ed
u/altmed/drugs/moxifloxacin-088848.ht
m) . University of Maryland Medical
Center. 2009. Archived from the original (h
ttp://www.umm.edu/altmed/drugs/moxifl
oxacin-088848.htm) on 7 March 2009.
Retrieved 22 July 2009.
36. "Microsoft Word - Rote Hand Brief Avalox
an BfArM.doc" (http://www.akdae.de/Arzn
eimittelsicherheit/RHB/Archiv/2009/2009
0119.pdf) (PDF). Retrieved 7 June 2019.
37. Nightingale CH (March 2000).
"Moxifloxacin, a new antibiotic designed
to treat community-acquired respiratory
tract infections: a review of microbiologic
and pharmacokinetic-pharmacodynamic
characteristics". Pharmacotherapy. 20 (3):
245–256.
doi:10.1592/phco.20.4.245.34880 (http
s://doi.org/10.1592%2Fphco.20.4.245.348
80) . PMID 10730681 (https://pubmed.nc
bi.nlm.nih.gov/10730681) .
S2CID 11448163 (https://api.semanticsch
olar.org/CorpusID:11448163) .
38. U.S. Food and Drug Administration (15
December 1999). "RE: NDA # 21-085
Avelox (moxifloxacin hydrochloride)
Tablets MACMIS # 8577" (https://web.arc
hive.org/web/20090309204016/https://w
ww.fda.gov/cder/warn/dec99/wl121599.p
df) (PDF). Letter to Martina Ziska.
Archived from the original (https://www.fd
a.gov/cder/warn/dec99/wl121599.pdf)
(PDF) on 9 March 2009. Retrieved 11 April
2009.
39. Albrecht R (16 May 2002). "NDA 21-085/S-
012" (http://www.accessdata.fda.gov/dru
gsatfda_docs/appletter/2002/21-085s012
ltr.pdf) (PDF). Food and Drug
Administration (FDA). Retrieved 17 July
2009.
40. Drlica K, Zhao X (September 1997). "DNA
gyrase, topoisomerase IV, and the 4-
quinolones" (https://www.ncbi.nlm.nih.go
v/pmc/articles/PMC232616) .
Microbiology and Molecular Biology
Reviews. 61 (3): 377–392.
doi:10.1128/mmbr.61.3.377-392.1997 (htt
ps://doi.org/10.1128%2Fmmbr.61.3.377-3
92.1997) . PMC 232616 (https://www.ncb
i.nlm.nih.gov/pmc/articles/PMC232616) .
PMID 9293187 (https://pubmed.ncbi.nlm.
nih.gov/9293187) .
41. "Drug card for Moxifloxacin (DB00218)" (ht
tp://www.drugbank.ca/drugs/DB00218) .
Canada: DrugBank. 19 February 2009.
Retrieved 3 August 2009.
42. Alffenaar JW, van Altena R, Bökkerink HJ,
Luijckx GJ, van Soolingen D, Aarnoutse RE,
van der Werf TS (October 2009).
"Pharmacokinetics of moxifloxacin in
cerebrospinal fluid and plasma in patients
with tuberculous meningitis" (https://doi.o
rg/10.1086%2F605576) . Clinical
Infectious Diseases. 49 (7): 1080–1082.
doi:10.1086/605576 (https://doi.org/10.1
086%2F605576) . PMID 19712035 (http
s://pubmed.ncbi.nlm.nih.gov/19712035) .
43. Peterson U (2006). "Quinolone Antibiotics:
The Development of Moxifloxacin" (http
s://books.google.com/books?id=FjKfqkaK
kAAC&q=discovery+benzylamine&pg=PA3
38) . In Fischer J, Ganellin CR (eds.).
Analogue-based Drug Discovery. John
Wiley & Sons. pp. 338–342.
ISBN 9783527607495.
44. "Inventors/Applicants" (https://archive.tod
ay/20130221225050/http://www.patentle
ns.net/patentlens/search_ajax.cgi?patnu
m=US/7115744) . patentlens.net. 3
October 2006. Archived from the original
(http://www.patentlens.net/patentlens/se
arch_ajax.cgi?patnum=US/7115744) on
21 February 2013. Retrieved 17 July 2009.
45. Lamb E (1 May 2008). "Top 200
Prescription Drugs of 2007" (https://web.a
rchive.org/web/20090207090521/http://p
harmacytimes.com/issues/articles/2008-
05_003.asp) . Pharmacy Times. Archived
from the original (http://www.pharmacyti
mes.com/issues/articles/2008-05_003.as
p) on 7 February 2009. Retrieved 21 July
2009.
46. "EU agency recommends restricting
moxifloxacin use" (https://www.reuters.co
m/article/rbssHealthcareNews/idUSL245
3307820080724) . Reuters. 24 July 2008.
Retrieved 21 July 2009.
47. "Alcon's Newest Antibiotic, Vigamox
Ophthalmic Solution, Earns FDA Approval"
(http://www.infectioncontroltoday.com/ne
ws/2003/04/alcon-s-newest-antibiotic-vig
amox-ophthalmic-solu.aspx) . Infection
Control Today. Alcon. 22 June 2003.
Retrieved 25 June 2016.
48. "Patent form" (http://www.uspto.gov/web/
offices/pac/dapp/opla/term/certs/49905
17.pdf) (PDF). uspto.gov. 1 February
1991. Retrieved 7 June 2019.
49. US 4990517 A (Feb 1991) Petersen et al.
See [1] (https://archive.today/2012091100
0730/http://www.patentlens.net/patentlen
s/search_ajax.cgi?patnum=US+4990517%
23list) US 5051509 A (Sep 1991) Nagano
et al. See [2] (https://archive.today/20120
912001450/http://www.patentlens.net/pat
entlens/search_ajax.cgi?patnum=US+505
1509%23list) US 5059597 A (Oct 1991)
Petersen et al. See [3] (https://archive.tod
ay/20120909180717/http://www.patentle
ns.net/patentlens/search_ajax.cgi?patnu
m=US+5059597%23list) US 5395944 A
(Mar 1995) Petersen et al. See [4] (https://
archive.today/20120906063537/http://ww
w.patentlens.net/patentlens/search_ajax.
cgi?patnum=US+5395944%23list) US
 5416096 A (May 1995) Petersen et al. See
[5] (https://archive.today/2012090601405
8/http://www.patentlens.net/patentlens/s
earch_ajax.cgi?patnum=US+5416096%23li
st)
50. "Updated Labelling for Antibiotic Avelox
(Moxifloxacin) Regarding Rare Risk of
Severe Liver Injury" (http://www.hc-sc.gc.c
a/ahc-asc/media/advisories-avis/_2010/2
010_42-eng.php) . Health Cananda. 22
March 2010. "Information Update: 2010-
42"
51. Albrecht R (3 October 2008). "NDA 21-
085/S-040, NDA 21-277/S-034" (http://ww
w.accessdata.fda.gov/drugsatfda_docs/a
ppletter/2008/021085s040,%20021277s0
34ltr.pdf) (PDF). Center for Drug
Evaluation and Research. Food and Drug
Administration. Retrieved 31 July 2009.
52. Bayer AG (6 November 2007). "Ruling in
Bayer's favor over Avelox patents" (https://
web.archive.org/web/20081211130541/ht
tp://www.stockholders-newsletter-q3-07.b
ayer.com/en/Avelox-patents.aspx) . Bayer.
Archived from the original (http://www.sto
ckholders-newsletter-q3-07.bayer.com/en/
avelox-patents.aspx) on 11 December
2008. Retrieved 29 August 2009.
53. "Opinion form" (http://www.orangebookblo
g.com/Bayer_20v._20Dr._20Reddy_27s.pd
f) (PDF). orangebookblog.com. 5 October
2007. Retrieved 7 June 2019.
54. "United States Court of Appeals for the
Federal Circuit" (https://web.archive.org/w
eb/20090826202547/http://www.cafc.usc
ourts.gov/opinions/06-1329.pdf) (PDF).
uscourts.gov. 28 June 2007. Archived
from the original (http://www.cafc.uscourt
s.gov/opinions/06-1329.pdf) (PDF) on 26
August 2009. Retrieved 29 August 2009.
55. Bayer AG (24 April 2008). "Risk Report" (ht
tps://web.archive.org/web/200903090145
17/http://www.stockholders-newsletter-q1
-08.bayer.com/en/Risk-Report.aspx) .
Bayer. Archived from the original (http://w
ww.stockholders-newsletter-q1-08.bayer.c
om/en/Risk-Report.aspx) on 9 March
2009. Retrieved 29 August 2009.

External links
"Moxifloxacin" (https://druginfo.nlm.nih.
gov/drugportal/name/moxifloxacin) .
Drug Information Portal. U.S. National
Library of Medicine.
"Moxifloxacin hydrochloride" (https://dru
ginfo.nlm.nih.gov/drugportal/name/mox
 ifloxacin%20hydrochloride) . Drug
Information Portal. U.S. National Library
of Medicine.

Portal:  Medicine

Retrieved from
"https://en.wikipedia.org/w/index.php?
title=Moxifloxacin&oldid=1129508663"

This page was last edited on 25 December 2022,

at 20:04 (UTC). •
Content is available under CC BY-SA 3.0 unless
otherwise noted.