MOXIFLOXACIN

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 Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s061s062,021277s057s058lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Topoisomerase IV subunit A 7 Target ID: CHEMBL4088 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16337789	Inhibitor 8504		800.0 nM [IC50]
DNA gyrase subunit A 7 Target ID: CHEMBL4165 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20516287	Inhibitor 8504		9200.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Community acquired pneumonia 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s061s062,021277s057s058lbl.pdf	Curative	Approved 8583	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
Plague 14 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s061s062,021277s057s058lbl.pdf	Curative	Approved 8583	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
Acute bacterial sinusitis 26 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s061s062,021277s057s058lbl.pdf	Curative	Approved 8583	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

C_max

Value	Dose	Analyte	Population
443.07 ng/ml Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01296191	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:
3.1 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
4.5 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
3.9 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
4.2 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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

AUC

Value	Dose	Analyte	Population
36.1 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
48 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
39.3 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
38 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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

T_1/2

Value	Dose	Analyte	Population
13.55 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
12.7 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
11.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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
14.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
60% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021085s063lbl.pdf	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63611	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63611
eMolecules	6843461	https://www.emolecules.com/cgi-bin/more?vid=6843461
MolPort	MolPort-006-167-494	https://www.molport.com/shop/molecule-link/MolPort-006-167-494
ZINC	ZINC000003826253	http://zinc15.docking.org/substances/ZINC000003826253

PubMed

Title	Date	PubMed
In vitro activity of Bay 12-8039, a new 8-methoxyquinolone.	1997-08	9257770

Patents

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 Created by `admin` on `Wed Apr 02 08:33:19 GMT 2025` Edited by `admin` on `Wed Apr 02 08:33:19 GMT 2025`
Record UNII	U188XYD42P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MOXIFLOXACIN

Official Name

English

AVELOX IV

Preferred Name

English

moxifloxacin [INN]

Common Name

English

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

Common Name

English

Moxifloxacin [WHO-DD]

Common Name

English

MOXIFLOXACIN [VANDF]

Common Name

English

ZIMOXIN

Brand Name

English

MOXIFLOXACIN [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

S01AX22