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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21ClFN3O3.ClH
Molecular Weight 430.301
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BESIFLOXACIN HYDROCHLORIDE

SMILES

Cl.N[C@@H]1CCCCN(C1)C2=C(F)C=C3C(=O)C(=CN(C4CC4)C3=C2Cl)C(O)=O

InChI

InChIKey=PMQBICKXAAKXAY-HNCPQSOCSA-N
InChI=1S/C19H21ClFN3O3.ClH/c20-15-16-12(18(25)13(19(26)27)9-24(16)11-4-5-11)7-14(21)17(15)23-6-2-1-3-10(22)8-23;/h7,9-11H,1-6,8,22H2,(H,26,27);1H/t10-;/m1./s1

HIDE SMILES / InChI

Description

Besifloxacin (INN/USAN) is a fourth-generation fluoroquinolone antibiotic. The marketed compound is Besifloxacin hydrochloride. It was developed by SSP Co. Ltd., Japan, and designated SS734. SSP licensed U.S. and European rights to SS734 for ophthalmic use to InSite Vision Incorporated in 2000. InSite Vision developed an eye drop formulation (ISV-403) and conducted preliminary clinical trials before selling the product and all rights to Bausch & Lomb in 2003. Besifloxacin is indicated in the treatment of bacterial conjunctivitis caused by sensitive germs, as well as in the prevention of infectious complications in patients undergoing laser therapy for the treatment of cataracts. Besifloxacin inhibits bacterial DNA gyrase and topoisomerase IV and has a broad spectrum of bactericidal activity against strains commonly isolated from patients with bacterial conjunctivitis. In addition, some exploratory in vitro data suggest that Besifloxacin inhibits cytokine formation in human corneal epithelial cells and monocytes, but the relevance of this finding to therapeutic efficacy is unknown.

Originator

Approval Year

2009
359
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
BESIVANCE

Approved Use

INDICATIONS AND USAGE. Besivance® (besifloxacin ophthalmic suspension) 0.6%, is a quinolone antimicrobial indicated for the treatment of bacterial conjunctivitis caused by susceptible isolates of the following bacteria: Aerococcus viridans *, CDC coryneform group G, Corynebacterium pseudodiphtheriticum*, Corynebacterium striatum*, Haemophilus influenzae Moraxella catarrhalis*, Pseudomonas aeruginosa *, Moraxella lacunata*, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus hominis*, Staphylococcus lugdunensis*, Staphylococcus warneri*, Streptococcus mitis group, Streptococcus oralis, Streptococcus pneumoniae, Streptococcus salivarius* *Efficacy for this organism was studied in fewer than 10 infections.

Launch Date

2009
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
610 μg/g
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19492955/
1 drop 4 times / day multiple, oral
dose: 1 drop
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BESIFLOXACIN cornea
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.37 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022308s013lbl.pdf
1 drop single, ocular
dose: 1 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
BESIFLOXACIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
56.4525 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:
BESIFLOXACIN aqueous humor
Homo sapiens
population: unhealthy
age:
sex:
food status:
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.232 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19492955/
1 drop 4 times / day multiple, oral
dose: 1 drop
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BESIFLOXACIN cornea
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19492955/
1 drop 4 times / day multiple, oral
dose: 1 drop
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BESIFLOXACIN cornea
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022308s013lbl.pdf
1 drop single, ocular
dose: 1 drop
route of administration: Ocular
experiment type: SINGLE
co-administered:
BESIFLOXACIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 drop 3 times / day multiple, topical
Recommended
Dose: 1 drop, 3 times / day
Route: topical
Route: multiple
Dose: 1 drop, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022308s013lbl.pdf
Page: p.3
unhealthy
Health Status: unhealthy
Condition: Bacterial conjunctivitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022308s013lbl.pdf
Page: p.3
Disc. AE: Bacterial resistance...
AEs leading to
discontinuation/dose reduction:
Bacterial resistance
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022308s013lbl.pdf
Page: p.3
AEs

AEs

AESignificanceDosePopulation
Bacterial resistance Disc. AE
1 drop 3 times / day multiple, topical
Recommended
Dose: 1 drop, 3 times / day
Route: topical
Route: multiple
Dose: 1 drop, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022308s013lbl.pdf
Page: p.3
unhealthy
Health Status: unhealthy
Condition: Bacterial conjunctivitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022308s013lbl.pdf
Page: p.3
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
111
CYP
270
CYP
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
147
 unlikely
CYP
147
 unlikely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
AK Scientific, Inc. (AKSCI)
Z6122
http://www.aksci.com/item_detail.php?cat=Z6122
Achemtek
0102-013346
http://www.achemtek.com/141388-76-3
ChemMol
30114323
http://www.chemmol.com/chemmol/30114323.html
ChemMol
49400296
http://www.chemmol.com/chemmol/49400296.html
Glentham Life Sciences
GA3299
http://www.glentham.com/products/product/GA3299/
Hairui
HR104538
http://www.hairuichem.com/en/product/141388-76-3.html
Matrix Scientific
120837
https://www.matrixscientific.com/120837.html
OChem
24101
http://www.ocheminc.com/index.php?act=psearch&pid=388B763
Selleck Chemicals
S5941
http://www.selleckchem.com/products/besifloxacin.html
Smolecule
S638463
https://www.smolecule.com/products/s638463
THE BioTek
bt-342289
https://www.thebiotek.com/product/others/bt-342289
iChemical
EBD24458
http://www.ichemical.com/chemicals/cas-141388-76-3
PubMed

PubMed

TitleDatePubMed
Besifloxacin, a new ophthalmic fluoroquinolone for the treatment of bacterial conjunctivitis.
2009 Oct
Efficacy of besifloxacin in a rabbit model of methicillin-resistant Staphylococcus aureus keratitis.
2009 Oct
Safety and tolerability of besifloxacin ophthalmic suspension 0.6% in the treatment of bacterial conjunctivitis: data from six clinical and phase I safety studies.
2010
An anterior chamber toxicity study evaluating Besivance, AzaSite, and Ciprofloxacin.
2010 Oct
Aqueous penetration of moxifloxacin 0.5% ophthalmic solution and besifloxacin 0.6% ophthalmic suspension in cataract surgery patients.
2010 Sep
Besifloxacin ophthalmic suspension, 0.6%: a novel topical fluoroquinolone for bacterial conjunctivitis.
2012 Jun
Patents

Patents

US20080306038
2

Sample Use Guides

In Vivo Use Guide
Instill one drop in the affected eye(s) 3 times a day, four to twelve hours apart for 7 days.
Route of Administration: Topical
In Vitro Use Guide
HEK-293 cells stably transfected with HERG-1 cDNA were exposed to SS734 (Besifloxacin) in Tyrode’s solution. Patch-clamp techniques were used to monitor the HERG current in individual cells. The HERG tail current was inhibited by only 13% when cells were exposed to 100 mkM SS734.
Name Type Language
BESIFLOXACIN HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
SS734
Code English
BESIFLOXACIN HCL
Common Name English
BESIFLOXACIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
3-QUINOLINECARBOXYLIC ACID, 7-((3R)-3-AMINOHEXAHYDRO-1H-AZEPIN-1-YL)-8-CHLORO-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-, MONOHYDROCHLORIDE
Common Name English
Besifloxacin hydrochloride [WHO-DD]
Common Name English
BESIFLOXACIN HYDROCHLORIDE [MI]
Common Name English
BESIVANCE
Brand Name English
BOL-303224-A
Code English
SS-734
Code English
BESIFLOXACIN (AS HYDROCHLORIDE)
Common Name English
(+)-7-((3R)-3-AMINOHEXAHYDRO-1H-AZEPIN-1-YL)-8-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID HYDROCHLORIDE
Systematic Name English
BESIFLOXACIN HYDROCHLORIDE [USAN]
Common Name English
BESIFLOXACIN HYDROCHLORIDE [VANDF]
Common Name English
BESIFLOXACIN HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
Code System Code Type Description
MERCK INDEX
m2448
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY Merck Index
SMS_ID
100000143395
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
NCI_THESAURUS
C76228
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
USAN
TT-06
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
CAS
405165-61-9
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
DRUG BANK
DBSALT000018
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201760
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID20193529
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
PUBCHEM
10224595
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
FDA UNII
7506A6J57T
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
EVMPD
SUB120189
Created by admin on Fri Dec 15 15:30:15 GMT 2023 , Edited by admin on Fri Dec 15 15:30:15 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of BESIFLOXACIN
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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