BESIFLOXACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H21ClFN3O3
Molecular Weight	393.84
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=QFFGVLORLPOAEC-SNVBAGLBSA-N

InChI=1S/C19H21ClFN3O3/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)/t10-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H21ClFN3O3
Molecular Weight	393.84
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Targets

Primary Target	Pharmacology	Condition	Potency
Topoisomerase IV 62	Inhibitor 8,297
Bacterial DNA gyrase 66	Inhibitor 8,297
Topoisomerase IV 62	Inhibitor 8,297
Bacterial DNA gyrase 66	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial conjunctivitis 34	Curative		Approved 8,429	BESIVANCE

C_max

Value	Dose	Analyte	Population
610 μg/g	1 drop 4 times / day multiple, oral	BESIFLOXACIN cornea	Homo sapiens
0.37 ng/mL	1 drop single, ocular	BESIFLOXACIN plasma	Homo sapiens
56.4525 ng/ml	1 drop 4 times / day multiple, ocular	BESIFLOXACIN aqueous humor	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1.232 μg × h/mL	1 drop 4 times / day multiple, oral		BESIFLOXACIN cornea	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.4 h	1 drop 4 times / day multiple, oral		BESIFLOXACIN cornea	Homo sapiens
7 h	1 drop single, ocular		BESIFLOXACIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
1 drop 3 times / day multiple, topical Recommended	unhealthy	Disc. AE: Bacterial resistance...

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AEs

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AE	Significance	Dose	Population
Bacterial resistance	Disc. AE	1 drop 3 times / day multiple, topical Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 111	CYP 270	CYP 76

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP 147	inducer 1,573	unlikely
CYP 147	inhibitor 3,277	unlikely

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
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/

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PubMed

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Title	Date	PubMed
Besifloxacin ophthalmic suspension for bacterial conjunctivitis.	2009 Aug	19927224
Besifloxacin, a new ophthalmic fluoroquinolone for the treatment of bacterial conjunctivitis.	2009 Oct	19743941
Comparative efficacy of besifloxacin and other fluoroquinolones in a prophylaxis model of penicillin-resistant Streptococcus pneumoniae rabbit endophthalmitis.	2010 Jun	20565309
Besifloxacin ophthalmic suspension, 0.6%: a novel topical fluoroquinolone for bacterial conjunctivitis.	2012 Jun	22729919

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Patents

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.