Besifloxacin

Besifloxacin

File:Besifloxacin.png
File:Besifloxacin-3D-balls.png
Systematic (IUPAC) name
7-[(3R)-3-Aminoazepam-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Clinical data
Trade names	Besivance
AHFS/Drugs.com	monograph
MedlinePlus	a610011
Licence data	US FDA:link
Legal status	US: ℞-only
Routes of administration	Ophthalmic
Identifiers
CAS Number	141388-76-3
ATC code	S01AE08 (WHO)
PubChem	CID: 10178705
ChemSpider	8354210
UNII	BFE2NBZ7NX Y
ChEMBL	CHEMBL1201760
Chemical data
Formula	C19H21ClFN3O3
Molecular mass	393.84 g·mol−1
SMILES Fc1c(c(Cl)c2c(c1)C(=O)C(\C(=O)O)=C/N2C3CC3)N4CCCC[C@@H](N)C4
InChI 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 Key:QFFGVLORLPOAEC-SNVBAGLBSA-N

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 (OTCBB: INSV) 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.

The eye drop was approved by the United States Food and Drug Administration (FDA) on May 29, 2009 and marketed under the trade name Besivance.

Pharmacodynamics

Besifloxacin is a fluoroquinolone that has a broad spectrum in vitro activity against a wide range of Gram-positive and Gram-negative ocular pathogens: e.g., Corynebacterium pseudodiphtheriticum, Moraxella lacunata, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus hominis, Streptococcus mitis, Streptococcus oralis, Streptococcus pneumoniae and Streptococcus salivarius. Besifloxacin has been found to inhibit production of pro-inflammatory cytokines in vitro. The mechanism of action of besifloxacin involves inhibition of two enzymes which are essential for the synthesis and replication of bacterial DNA: the bacterial DNA gyrase and topoisomerase IV.

Medical Use

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.

Adverse Effects

During the treatment, the most frequently reported ocular adverse reaction was the appearance of conjunctival redness (approximately 2% of patients). Other possible adverse reactions, reported in subjects treated with besifloxacin were: eye pain, itching of the eye, blurred vision, swelling of the eye or eyelid.