Besifloxacin

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Besifloxacin
Besifloxacin structure.png
Besifloxacin-3D-balls.png
Names
Trade namesBesivance
Other namesBesifloxacin hydrochloride
  • 7-[(3R)-3-Aminoazepam-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Clinical data
Drug classAntibiotic (fluoroquinolone)[1]
Main usesBacterial conjunctivitis[2]
Side effectsRedness of the eye[2]
Routes of
use
Ophthalmic
External links
AHFS/Drugs.comMonograph
US NLMBesifloxacin
MedlinePlusa610011
Legal
License data
Legal status
Chemical and physical data
FormulaC19H21ClFN3O3
Molar mass393.84 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, sold under the brand name Besivance, is an antibiotic used to treat bacterial conjunctivitis.[2] It is used as an eye drop.[2]

Common side effects include redness of the eye.[2] Other side effects may include allergic reactions.[1] Safety in pregnancy is unclear.[1] It is a fluoroquinolone and works by blocking DNA topoisomerases.[1]

Besifloxacin was approved for medical use in the United States in 2009.[2] In the United States a 5 ml bottle costs about 210 USD as of 2022.[3]

Medical use

Besifloxacin is indicated in the treatment of bacterial conjunctivitis caused by sensitive germs,[4] as well as in the prevention of infectious complications in patients undergoing laser therapy for the treatment of cataracts.[5][6]

Dosage

It is used as one drop three times per day for 7 days.[2] It comes as a 0.6% solution.[1]

Side 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.

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.[7] 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.

References

  1. 1.0 1.1 1.2 1.3 1.4 "Besifloxacin Monograph for Professionals". Drugs.com. Retrieved 10 January 2022.
  2. 2.0 2.1 2.2 2.3 2.4 2.5 2.6 "DailyMed - BESIVANCE- besifloxacin suspension". dailymed.nlm.nih.gov. Retrieved 10 January 2022.
  3. "Besivance Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 10 January 2022.
  4. 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.
  5. 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.
  6. 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.
  7. 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.

External links

Identifiers: