Norfloxacin

Norfloxacin
Clinical data
Trade names	Noroxin, Chibroxin, Trizolin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a687006
Routes of; administration	Oral, ophthalmic
ATC code	J01MA06 (WHO) S01AE02 (WHO);
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	30 to 40%
Protein binding	10 to 15%
Metabolism	Hepatic
Elimination half-life	3 to 4 hours
Excretion	Renal and fecal
Identifiers
	IUPAC name 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1H-quinoline-; 3-carboxylic acid;
CAS Number	70458-96-7 ;
PubChem CID	4539;
DrugBank	DB01059 ;
ChemSpider	4380 ;
UNII	N0F8P22L1P;
KEGG	D00210 ;
ChEBI	CHEBI:100246 ;
ChEMBL	ChEMBL9 ;
CompTox Dashboard (EPA)	DTXSID7037680 ;
ECHA InfoCard	100.067.810
Chemical and physical data
Formula	C16H18FN3O3
Molar mass	319.336 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	220 to 221 °C (428 to 430 °F)
	SMILES O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCNCC3)CC;
	InChI 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) ; Key:OGJPXUAPXNRGGI-UHFFFAOYSA-N ;
	(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]

^ 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.
^ 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.
^ "TABLETS NOROXIN (NORFLOXACIN)" (PDF). Merck Sharp & Dohme. USA: FDA. September 2008. Archived from the original (PDF) on October 19, 2010.
^ "Norfloxacin" (PDF). Davis. 2017. Archived from the original (PDF) on October 27, 2017. Retrieved March 24, 2017.
^ 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.
^ Cite error: The named reference accessdata.fda.gov was invoked but never defined (see the help page).
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 9783527607495.

[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.

[fda08-3] "TABLETS NOROXIN (NORFLOXACIN)" (PDF). Merck Sharp & Dohme. USA: FDA. September 2008. Archived from the original (PDF) on October 19, 2010.

[Davisnorflox-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.

[accessdata.fda.gov-6] Cite error: The named reference accessdata.fda.gov was invoked but never defined (see the help page).

[pmid26393387-7] 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.

[Fis2006-8] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 9783527607495.

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