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Ofloxacin
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| Systematic (IUPAC) name | |
| (+/-)-9-fluoro-2, 3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)- 7-oxo-7H-pyrido [1,2,3-de]-1, 4-benzoxazine-6-carboxylic acid | |
| Identifiers | |
| CAS number | |
| ATC code | J01 J01, J01, S01, S01, S01, S03 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C18H20FN3O4 |
| Mol. mass | 361.368 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Protein binding | 32% |
| Metabolism | ? |
| Half life | 9 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
C(US) |
| Legal status | |
| Routes | Oral, topical (eye drops and ear drops) |
Ofloxacin (sold under the brand name Floxin in the United States, Tarivid in Europe and some other countries) is a fluoroquinolone antibiotic. Ofloxacin is the racemic mixture of the chiral compound. The biologically active enantiomer is sold separately under the name of levofloxacin. It has been used as a treatment for gonorrhoea and chlamydia infection and is an alternative treatment to ciprofloxacin for anthrax. Like all quinolones, ofloxacin is not effective in the treatment of syphilis.1
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Adverse effects
- See also: Levofloxacin#Adverse effects
The side effects of ofloxacin are similar to those of other fluoroquinolone antibiotics. The most common adverse effects are headache, nausea, insomnia, dizziness, and diarrhea.2 Serious, rare side effects (also common to all fluoroquinolones) include: tendon damage, known as quinolone-induced tendonopathy; irreversible peripheral neuropathy; QT prolongation; central nervous system effects such as dizziness, insomnia, anxiety, tremors, and even hallucinations and seizures; and abnormal blood sugar levels (hypoglycemia and hyperglycemia, even in people who do not have diabetes).23
Ofloxacin crosses the placenta, and fluoroquinolones have been shown to cause fetal harm in animals; it is therefore not recommended for use by pregnant women. It also passes into breast milk, and should not be used by women who are breastfeeding.2
Tendon rupture
As with all fluoroquinolones, there is a possibility of spontaneous tendon rupture.4 Such ruptures may occur both during therapy and long after therapy has been discontinued; there are documented cases where rupture has occurred six months after therapy.4 The risk of tendon damage is greater in people taking corticosteroids and in the elderly.5
Since July 2008, all systemic fluoroquinolones (those taken internally, not as eye drops or ear drops) available in the United States must carry a boxed warning warning of the risk of tendon damage.5
References
- ^ Tartaglione TA, Hooton TM (1993). "The role of fluoroquinolones in sexually transmitted diseases". Pharmacotherapy 13 (3): 189–201. PMID 8321733.
- ^ a b c Lexi-Comp (August 2008). "Ofloxacin". The Merck Manual Professional. Retrieved on October 11, 2008.
- ^ Mehlhorn AJ, Brown DA (November 2007). "Safety concerns with fluoroquinolones". The Annals of Pharmacotherapy 41 (11): 1859–66. doi:. PMID 17911203.
- ^ a b Khaliq Y, Zhanel GG (June 2003). "Fluoroquinolone-associated tendinopathy: a critical review of the literature". Clinical Infectious Diseases 36 (11): 1404–10. doi:. PMID 12766835.
- ^ a b U.S. Food and Drug Administration (July 8, 2008). "FDA Requests Boxed Warnings on Fluoroquinolone Antimicrobial Drugs". Press release. Retrieved on October 11, 2008.
External links
- Ofloxacin: an overview - A site with its chemical properties and alternate brand names.
- [1] -Merck Manual link covering the class of fluoroquinolones antibacterials.
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Wikipedia content modification information:
- This page was last modified on 18 October 2008, at 17:54.
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