Besifloxacin

Last updated
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

<span class="mw-page-title-main">Conjunctivitis</span> Inflammation of the eye

Conjunctivitis, also known as pink 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.

<span class="mw-page-title-main">Ophthalmology</span> Field of medicine treating eye disorders

Ophthalmology is a surgical subspecialty within medicine that deals with the diagnosis and treatment of eye disorders.

<span class="mw-page-title-main">LASIK</span> Corrective ophthalmological surgery

LASIK or Lasik, commonly referred to as laser eye surgery or laser vision correction, is a type of refractive surgery for the correction of myopia, hyperopia, and an actual cure for astigmatism, since it is in the cornea. LASIK surgery is performed by an ophthalmologist who uses a laser or microkeratome to reshape the eye's cornea in order to improve visual acuity.

<span class="mw-page-title-main">Levofloxacin</span> Antibiotic

Levofloxacin, sold under the brand name Levaquin among others, is an antibiotic medication. It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, H. pylori, urinary tract infections, chronic prostatitis, and some types of gastroenteritis. Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease. Use is generally recommended only when other options are not available. It is available by mouth, intravenously, and in eye drop form.

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

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.

<span class="mw-page-title-main">Corneal cross-linking</span> Surgical procedure

Corneal cross-linking (CXL) with riboflavin (vitamin B2) and UV-A light is a surgical treatment for corneal ectasia such as keratoconus, PMD, and post-LASIK ectasia.

<span class="mw-page-title-main">Loteprednol</span> Pharmaceutical drug

Loteprednol is a topical corticosteroid used to treat inflammations of the eye. It is marketed by Bausch and Lomb as Lotemax and Loterex.

Ocular ischemic syndrome is the constellation of ocular signs and symptoms secondary to severe, chronic arterial hypoperfusion to the eye. Amaurosis fugax is a form of acute vision loss caused by reduced blood flow to the eye; it may be a warning sign of an impending stroke, as both stroke and retinal artery occlusion can be caused by thromboembolism due to atherosclerosis elsewhere in the body. Consequently, those with transient blurring of vision are advised to urgently seek medical attention for a thorough evaluation of the carotid artery. Anterior segment ischemic syndrome is a similar ischemic condition of anterior segment usually seen in post-surgical cases. Retinal artery occlusion leads to rapid death of retinal cells, thereby resulting in severe loss of vision.

<span class="mw-page-title-main">NicOx</span>

Nicox S.A. is a French ophthalmology company developing treatments to maintain vision and improve ocular health. Nicox is headquartered in Sophia Antipolis, France, and its Chairman and CEO is Michele Garufi.

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

Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) marketed in the US as an ophthalmic solution by ISTA Pharmaceuticals for short-term, local use. Prolensa and Bromday are the once-daily formulation of bromfenac, while Xibrom was approved for twice-daily administration. In the European Union, the brand name is Yellox. Bromfenac is indicated for the treatment of ocular inflammation and pain after cataract surgery.

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

Bepotastine is a 2nd generation antihistamine. It was approved in Japan for use in the treatment of allergic rhinitis and urticaria/pruritus in July 2000, and January 2002, respectively. It is marketed in the United States as an eye drop under the brand name Bepreve, by ISTA Pharmaceuticals, a subsidiary of Bausch + Lomb.

<span class="mw-page-title-main">ISTA Pharmaceuticals</span> US-based pharmaceutical company

ISTA Pharmaceuticals, Inc, was a US-based pharmaceutical company that specialized in ophthalmic pharmaceutical products and discovers, develops, and markets therapies for inflammation, ocular pain, glaucoma, allergy, and dry eye. ISTA was acquired by Bausch & Lomb, an eye care company, on March 26, 2012. Under the deal, Bausch & Lomb have agreed to pay $9.10 per share for ISTA, bringing the total value of the acquisition to $500 million.

<span class="mw-page-title-main">Mapracorat</span> Type of selective glucocorticoid receptor agonist

Mapracorat is an anti-inflammatory drug belonging to the experimental class of selective glucocorticoid receptor agonists (SEGRAs). It is in clinical trials for the topical treatment of atopic dermatitis, inflammation following cataract surgery, and allergic conjunctivitis. Preliminary investigation for the treatment of keratoconjunctivitis sicca has been conducted in cellular models.

<span class="mw-page-title-main">Alimera Sciences</span>

Alimera Sciences, Inc. is a biopharmaceutical company based in Alpharetta, Georgia that specializes in the commercialization and development of prescription ophthalmic pharmaceuticals. The company's main focus is on diseases affecting the back of the eye, or retina. Its main product is Iluvien, a fluocinolone acetonide intravitreal implant.

Diffuse lamellar keratitis (DLK) is a sterile inflammation of the cornea which may occur after refractive surgery, such as LASIK. Its incidence has been estimated to be 1 in 500 patients, though this may be as high as 32% in some cases.

Peter S. Hersh is an American ophthalmologist and specialist in LASIK eye surgery, keratoconus, and diseases of the cornea. He co-authored the article in the journal Ophthalmology that presented the results of the study that led to the first approval by the U.S. Food and Drug Administration (FDA) of the excimer laser for the correction of nearsightedness in the United States. Hersh was also medical monitor of the study that led to approval of corneal collagen crosslinking for the treatment of keratoconus.

Marguerite McDonald is an eye surgeon who in 1987 performed the first excimer laser treatment. In 1993 she became the first to use this treatment to treat farsightedness. In September 2003, she became the first person in North America to perform Epi-LASIK. She has also conducted the first wavefront-based laser surgeries in the United States. She was a co-developer of Kaufman-McDonald epikeratophakia.

Post-LASIK ectasia is a condition similar to keratoconus where the cornea starts to bulge forwards at a variable time after LASIK, PRK, or SMILE corneal laser eye surgery. However, the physiological processes of post-LASIK ectasia seem to be different from keratoconus. The visible changes in the basal epithelial cell and anterior and posterior keratocytes linked with keratoconus were not observed in post-LASIK ectasia.

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.