Besifloxacin

Besifloxacin
Names
Trade namesBesivance
Other namesBesifloxacin hydrochloride
IUPAC name
  • 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]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		Ophthalmic
External links
AHFS/Drugs.comMonograph
MedlinePlusa610011
Legal
License data
Legal status
Chemical and physical data
FormulaC19H21ClFN3O3
Molar mass393.84 g·mol−1
3D model (JSmol)
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, 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 2 3 4 5 "Besifloxacin Monograph for Professionals". Drugs.com. Archived from the original on 24 January 2021. Retrieved 10 January 2022.
  2. 1 2 3 4 5 6 7 "DailyMed - BESIVANCE- besifloxacin suspension". dailymed.nlm.nih.gov. Archived from the original on 24 March 2021. Retrieved 10 January 2022.
  3. ↑ "Besivance Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 16 August 2021. 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.
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