Norfloxacin
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| Clinical data | |
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| Trade names | Noroxin |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a687006 |
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| Routes of administration |
Oral,ophthalmic |
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| Pharmacokinetic data | |
| Bioavailability | 30 to 40% |
| Protein binding | 10 to 15% |
| Metabolism | Hepatic |
| Biological half-life | 3 to 4 hours |
| Excretion | Renal and fecal |
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| DrugBank | |
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| ChEMBL | |
| ECHA InfoCard | 100.067.810 |
| Chemical and physical data | |
| Formula | C16H18FN3O3 |
| Molar mass | 319.331 g/mol |
| 3D model (Jmol) | |
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Norfloxacin is a synthetic chemotherapeutic antibacterial agent used to treat urinary tract infections, gynecological infections, inflammation of the prostate gland, gonorrhea and bladder infection. It is sold under the brand name Noroxin.
Eye drops were approved for use in children older than one year of age.
Norfloxacin is associated with a number of rare serious adverse reactions as well as spontaneous tendon ruptures and irreversible peripheral neuropathy. Tendon problems may manifest long after therapy had been completed and in severe cases may result in lifelong disabilities.
The first members of the quinolone antibacterial class were relatively low potency drugs such as nalidixic acid, used mainly in the treatment of urinary tract infections owing to their renal excretion and propensity to be concentrated in urine. In 1979 the publication of a patent filed by the pharmaceutical arm of Kyorin Seiyaku Kabushiki Kaisha disclosed the discovery of norfloxacin, and the demonstration that certain structural modifications including the attachment of a fluorine atom to the quinolone ring leads to dramatically enhanced antibacterial potency.
In spite of the substantial increase in antibacterial activity of norfloxacin relative to early fluoroquinolones, it did not become a widely used antibiotic. Other companies initiated fluoroquinolone discovery programs in the aftermath of the publication of the norfloxacin patent. Bayer Pharmaceuticals discovered that the addition of a single carbon atom to the norfloxacin structure provided another 4 to 10-fold improvement in activity. Ciprofloxacin reached the market just one year after norfloxacin and achieved sales of 1.5 billion Euros at its peak.
Kyorin granted Merck & Company, Inc., an exclusive license (in certain countries, including the United States), to import and distribute Norfloxacin under the brand name Noroxin. The U.S. Food and Drug Administration (FDA) approved Noroxin for distribution in the United States on October 31, 1986.
The initial approval by the U.S. Food and Drug Administration (FDA) in 1986 encompassed the following indications:
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