Norfloxacin

Norfloxacin
Clinical data
Trade namesNoroxin, Chibroxin, Trizolin, others
AHFS/Drugs.comMonograph
MedlinePlusa687006
Routes of
administration		Oral, ophthalmic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability30 to 40%
Protein binding10 to 15%
MetabolismHepatic
Elimination half-life3 to 4 hours
ExcretionRenal and fecal
Identifiers
  • 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1H-quinoline-
    3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.067.810 Edit this at Wikidata
Chemical and physical data
FormulaC16H18FN3O3
Molar mass319.336 g·mol−1
3D model (JSmol)
Melting point220 to 221 °C (428 to 430 °F)
  • O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCNCC3)CC
  • InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23) checkY
  • Key:OGJPXUAPXNRGGI-UHFFFAOYSA-N checkY
  (verify)

Norfloxacin, sold under the brand name Noroxin among others, is an antibiotic[1][2] that belongs to the class of fluoroquinolone antibiotics. It is used to treat urinary tract infections, gynecological infections, inflammation of the prostate gland, gonorrhea and bladder infection.[3][4][5] Eye drops were approved for use in children older than one year of age.[6]

Norfloxacin is associated with a number of rare serious adverse reactions as well as spontaneous tendon ruptures[7] and irreversible peripheral neuropathy. Tendon problems may manifest long after therapy had been completed and in severe cases may result in lifelong disabilities.

It was patented in 1977 and approved for medical use in 1983.[8]

  1. ^ Nelson JM, Chiller TM, Powers JH, Angulo FJ (April 2007). "Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: a public health success story". Clinical Infectious Diseases. 44 (7): 977–980. doi:10.1086/512369. PMID 17342653.
  2. ^ Padeĭskaia EN (2003). "[Norfloxacin: more than 20 years of clinical use, the results and place among fluoroquinolones in modern chemotherapy for infections]". Antibiotiki I Khimioterapiia = Antibiotics and Chemoterapy [Sic]. 48 (9): 28–36. PMID 15002177.
  3. ^ "TABLETS NOROXIN (NORFLOXACIN)" (PDF). Merck Sharp & Dohme. USA: FDA. September 2008.
  4. ^ "Norfloxacin" (PDF). Davis. 2017. Archived from the original (PDF) on October 27, 2017. Retrieved March 24, 2017.
  5. ^ Rafalsky V, Andreeva I, Rjabkova E (July 2006). Rafalsky VV (ed.). "Quinolones for uncomplicated acute cystitis in women". The Cochrane Database of Systematic Reviews. 2006 (3): CD003597. doi:10.1002/14651858.CD003597.pub2. PMC 7003573. PMID 16856014.
  6. ^ Cite error: The named reference accessdata.fda.gov was invoked but never defined (see the help page).
  7. ^ Arabyat RM, Raisch DW, McKoy JM, Bennett CL (2015). "Fluoroquinolone-associated tendon-rupture: a summary of reports in the Food and Drug Administration's adverse event reporting system". Expert Opinion on Drug Safety. 14 (11): 1653–1660. doi:10.1517/14740338.2015.1085968. PMID 26393387. S2CID 25279196.
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 9783527607495.