Besifloxacin

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Besifloxacin
Besifloxacin.svg
Besifloxacin-3D-balls.png
Clinical data
Trade names Besivance
AHFS/Drugs.com Monograph
MedlinePlus a610011
License data
Routes of
administration
Ophthalmic
ATC code
Legal status
Legal status
Identifiers
  • 7-[(3R)-3-Aminoazepam-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H21ClFN3O3
Molar mass 393.84 g·mol−1
3D model (JSmol)
  • Fc1c(c(Cl)c2c(c1)C(=O)C(\C(=O)O)=C/N2C3CC3)N4CCCC[C@@H](N)C4
  • 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 (OTC Pink : 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. [1]

Contents

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. [2]

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 . [3] 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. Clinical trials indicated that Besifloxacin was 91% effective at eliminating the causative bacteria after five days, compared to 60% in the placebo group. This did not, however necessarily correlate with condition resolution, as bacterial presence is only a part of conjunctivitis. [4]

Medical use

Besifloxacin is indicated in the treatment of bacterial conjunctivitis caused by sensitive bacteria, [5] as well as in the prevention of infectious complications in patients undergoing laser therapy for the treatment of cataracts. [6] [7] It has been approved for use in children, adults, and the elderly, with clinically proven efficacy and safety from age one and older. [4]

Besifloxacin is available as a 0.6% ophthalmological suspension, and dosing is 3 times a day, 4 to 12 hours apart for 7 days, regardless of age or condition. [4]

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: blurred vision, eye pain, eye irritation, eye pruritus and headache. [4]

Related Research Articles

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Conjunctivitis, also known as pink eye or Madras eye, is inflammation of the outermost layer of the white part of the eye and the inner surface of the eyelid. It makes the eye appear pink or reddish. Pain, burning, scratchiness, or itchiness may occur. The affected eye may have increased tears or be "stuck shut" in the morning. Swelling of the white part of the eye may also occur. Itching is more common in cases due to allergies. Conjunctivitis can affect one or both eyes. This was first Identified in Madras.

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<span class="mw-page-title-main">Dry eye syndrome</span> Medical condition of dry eyes

Dry eye syndrome, also known as keratoconjunctivitis sicca, is the condition of having dry eyes. Symptoms include dryness in the eye, irritation, redness, discharge, blurred vision, and easily fatigued eyes. Symptoms range from mild and occasional to severe and continuous. Dry eye syndrome can lead to blurred vision, instability of the tear film, increased risk of damage to the ocular surface such as scarring of the cornea, and changes in the eye including the neurosensory system.

<span class="mw-page-title-main">Allergic conjunctivitis</span> Medical condition

Allergic conjunctivitis (AC) is inflammation of the conjunctiva due to allergy. Although allergens differ among patients, the most common cause is hay fever. Symptoms consist of redness, edema (swelling) of the conjunctiva, itching, and increased lacrimation. If this is combined with rhinitis, the condition is termed allergic rhinoconjunctivitis (ARC).

The Lions Eye Institute (LEI) is an Australian medical research institute affiliated with the University of Western Australia. It was established in 1983 with support of the Lions Clubs of Western Australia and headquartered in the Perth suburb of Nedlands, Western Australia. The LEI is a not-for-profit centre of excellence that combines an ophthalmic clinic with scientific discovery developing techniques for the prevention of blindness and the reduction of pain from blinding eye conditions.

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<span class="mw-page-title-main">Corneal neovascularization</span> Medical condition

Corneal neovascularization (CNV) is the in-growth of new blood vessels from the pericorneal plexus into avascular corneal tissue as a result of oxygen deprivation. Maintaining avascularity of the corneal stroma is an important aspect of healthy corneal physiology as it is required for corneal transparency and optimal vision. A decrease in corneal transparency causes visual acuity deterioration. Corneal tissue is avascular in nature and the presence of vascularization, which can be deep or superficial, is always pathologically related.

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<span class="mw-page-title-main">Bromfenac</span> Chemical compound

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<span class="mw-page-title-main">Bepotastine</span> Chemical compound

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Lifitegrast, sold under the brand name Xiidra, is a medication for the treatment of signs and symptoms of dry eye, a syndrome called keratoconjunctivitis sicca. Lifitegrast reduces inflammation by inhibiting inflammatory cell binding. It is often used in conjunction with ciclosporin for dry eye treatment including meibomian gland dysfunction and inflammatory dry eye.

References

  1. "InSite Vision Reaches Agreement to Sell ISV-403 to Bausch & Lomb" (Press release). InSite Vision. 2003-12-19. Retrieved 2009-08-15.
  2. "Bausch & Lomb Receives FDA Approval of Besivance, New Topical Ophthalmic Antibacterial for the Treatment of Bacterial Conjunctivitis ("Pink Eye")" (Press release). Bausch & Lomb. 2009-05-29. Archived from the original on 2009-06-01. Retrieved 2009-05-29.
  3. Zhang JZ, Ward KW (January 2008). "Besifloxacin, a novel fluoroquinolone antimicrobial agent, exhibits potent inhibition of pro-inflammatory cytokines in human THP-1 monocytes". J. Antimicrob. Chemother. 61 (1): 111–6. doi:10.1093/jac/dkm398. PMID   17965029.
  4. 1 2 3 4 "Besivance Full Prescribing Info" (PDF). Bausch & Lomb. 02-01-2022. Retrieved 07-29-2022.
  5. Malhotra R, Ackerman S, Gearinger LS, Morris TW, Allaire C (December 2013). "The safety of besifloxacin ophthalmic suspension 0.6 % used three times daily for 7 days in the treatment of bacterial conjunctivitis". Drugs in R&D. 13 (4): 243–52. doi:10.1007/s40268-013-0029-1. PMC   3851703 . PMID   24142473.
  6. Majmudar PA, Clinch TE (May 2014). "Safety of besifloxacin ophthalmic suspension 0.6% in cataract and LASIK surgery patients". Cornea. 33 (5): 457–62. doi:10.1097/ICO.0000000000000098. PMC   4195578 . PMID   24637269.
  7. Nielsen SA, McDonald MB, Majmudar PA (2013). "Safety of besifloxacin ophthalmic suspension 0.6% in refractive surgery: a retrospective chart review of post-LASIK patients". Clinical Ophthalmology. 7: 149–56. doi: 10.2147/OPTH.S38279 . PMC   3552478 . PMID   23355771.