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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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H21ClFN3O3
Molecular Weight 393.84
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
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
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
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
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
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
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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Bacterial conjunctivitis
Sources: Page: p.3
Disc. AE: Bacterial resistance...
AEs leading to
discontinuation/dose reduction:
Bacterial resistance
Sources: 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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Bacterial conjunctivitis
Sources: Page: p.3
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Nonclinical pharmacodynamics, pharmacokinetics, and safety of BOL-303224-A, a novel fluoroquinolone antimicrobial agent for topical ophthalmic use.
2007 Jun
Besifloxacin, a novel fluoroquinolone antimicrobial agent, exhibits potent inhibition of pro-inflammatory cytokines in human THP-1 monocytes.
2008 Jan
Besifloxacin ophthalmic suspension for bacterial conjunctivitis.
2009 Aug
New drugs: golimumab, besifloxacin hydrochloride, and artemether/lumefantrine.
2009 Jul-Aug
Besifloxacin ophthalmic suspension 0.6% in patients with bacterial conjunctivitis: A multicenter, prospective, randomized, double-masked, vehicle-controlled, 5-day efficacy and safety study.
2009 Mar
Target specificity of the new fluoroquinolone besifloxacin in Streptococcus pneumoniae, Staphylococcus aureus and Escherichia coli.
2009 Mar
Phase III efficacy and safety study of besifloxacin ophthalmic suspension 0.6% in the treatment of bacterial conjunctivitis.
2009 May
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
Efficacy and safety of besifloxacin ophthalmic suspension 0.6% compared with moxifloxacin ophthalmic solution 0.5% for treating bacterial conjunctivitis.
2009 Sep
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
Besifloxacin ophthalmic suspension 0.6%.
2010
Efficacy of besifloxacin in an early treatment model of methicillin-resistant Staphylococcus aureus keratitis.
2010 Apr
Efficacy and safety of besifloxacin ophthalmic suspension 0.6% in children and adolescents with bacterial conjunctivitis: a post hoc, subgroup analysis of three randomized, double-masked, parallel-group, multicenter clinical trials.
2010 Apr 1
Penetration and effectiveness of prophylactic fluoroquinolones in experimental methicillin-sensitive or methicillin-resistant Staphylococcus aureus anterior chamber infections.
2010 Dec
New Drugs2010, PART 1.
2010 Feb
Bactericidal activity of besifloxacin against staphylococci, Streptococcus pneumoniae and Haemophilus influenzae.
2010 Jul
Comparative efficacy of besifloxacin and other fluoroquinolones in a prophylaxis model of penicillin-resistant Streptococcus pneumoniae rabbit endophthalmitis.
2010 Jun
Comparative effects of besifloxacin and other fluoroquinolones on corneal reepithelialization in the rabbit.
2010 Jun
Besifloxacin: a topical fluoroquinolone for the treatment of bacterial conjunctivitis.
2010 Mar
Ocular pharmacokinetics/pharmacodynamics of besifloxacin, moxifloxacin, and gatifloxacin following topical administration to pigmented rabbits.
2010 Oct
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

Sample Use Guides

Instill one drop in the affected eye(s) 3 times a day, four to twelve hours apart for 7 days.
Route of Administration: Topical
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:30:15 GMT 2023
Edited
by admin
on Fri Dec 15 15:30:15 GMT 2023
Record UNII
7506A6J57T
Record Status Validated (UNII)
Record Version
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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
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