Ofloxacin

Ofloxacin

Clinical data
Routes of administration	Topical (ear drops)
ATC code	J01MA01 (WHO) J01MA02 (WHO), J01MA12 (WHO), S01AX11 (WHO), S01AX13 (WHO), S01AX19 (WHO), S03AA07 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Protein binding	32%
Elimination half-life	9 hours
Identifiers
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
CAS Number	82419-36-1
PubChem CID	4583
DrugBank	APRD00502
CompTox Dashboard (EPA)	DTXSID3041085
ECHA InfoCard	100.205.209
Chemical and physical data
Formula	C18H20FN3O4
Molar mass	361.368 g/mol g·mol−1

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 is used as a treatment for gonorrhoea and is an alternative treatment to ciprofloxacin for anthrax.

Syphilis: Ofloxacin is not effective in the treatment of syphilis. Antimicrobial agents used in high doses for short periods of time to treat gonorrhea may mask or delay the symptoms of incubating syphilis.

Safety Profile:

In 2004 new warning labels added to all of the Fluoroquinolones regarding Peripheral Neuropathy (irreversible nerve damage), Tendon Damage, Heart Problems (prolonged QT Interval / Torsades de pointes), Pseudomembranous colitis, Rhabdomyolysis (muscle wasting), Steven Johnson Syndrome, as well as concurrent usage of NSAIDs contributing to the severity of these reactions.

This drug has similar side effects to all the other fluoroquinolone antibiotics.

As with all fluoroquinolones there are numerous documented cases of spontaneous tendon rupture. Such ruptures may occur both during as well as long after therapy had been discontinued. There are documented cases where such ruptures have occurred over a year later. It is impossible to calculate the risk of such ruptures as the medical community for the most part fails to associate tendon ruptures with the use of the drugs found within this class. Currently there are two petitions pending with the FDA seeking "Black Box Warnings" as well as "Dear Doctor Letters" regarding this particular adverse reaction. The medical journals have clearly associated such a risk with the fluoroquinolone class since their introduction back in 1982. The FDA has failed to respond to these petitions as required by law and Public Citizen has filed a lawsuit in Federal Court (January 2008) seeking a court order requiring compliance by the FDA. There are other cases of severe pain, and swelling in as little as two days. This is known as "quinolone-induced tendonopathy" and such injury appears to be a lifelong disability.

Within the recent label changes (2007) it is noted that:

"Post-marketing surveillance reports indicate that this risk may be increased in patients receiving concomitant corticosteroids, especially in the elderly...Ruptures of the shoulder, hand, and Achilles tendons that required surgical repair or resulted in prolonged disability have been reported in patients receiving quinolones. Tendon rupture can occur during or after therapy with quinolones. "

There are other serious adverse reactions associated with this class including Irreversible Peripheral Neuropathy, (permanent nerve damage), increased QT prolongation, Torsades de Pointes, central nervous system (CNS) events including severe nervousness, agitation, chronic insomnia, anxiety attacks, nightmares, and paranoia. Toxic Psychosis has also been reported.

Life threatening disturbances of blood glucose, including symptomatic hyper- and hypoglycemia, are also associated with the use of the fluoroquinolones.

Fluoroquinolones caused fetal harm in animal studies, including decreased body weights and malformed bones as well as an increased risk of death. Because of the potential for serious adverse effects to the fetus, these drugs should not be used by pregnant women.

Fluoroquinolones are excreted in human milk. Because of the potential for serious adverse effects in nursing infants, you should not take these drugs while nursing.

Other adverse events found within the package inserts for Ofloxacin include the following:

Cardiovascular: Palpitation, atrial flutter, ventricular ectopy, syncope, hypertension, angina pectoris, myocardial infarction, cardiopulmonary arrest, cerebral thromobosis. Cardiovascular collapse, cardiopulmonary arrest, myocardial infarction, arrhythmia, tachycardia, palpitation, cerebral thrombosis, syncope, cardiac murmur, hypertension, hypotension, angina pectoris. Postural hypotension, vasculitis.

Central Nervous System: Dizziness, lightheadedness, insomnia, nightmares, hallucinations, manic reaction, irritability, tremor, ataxia, convulsive seizures, lethargy, drowsiness, weakness, malaise, anorexia, phobia, depersonalization, depression, paresthesia. Convulsive seizures, paranoia, toxic psychosis, depression, dysphasia, phobia, depersonalization, manic reaction, unresponsiveness, ataxia, confusion, hallucinations, dizziness, lightheadedness, paresthesia, anxiety, tremor, insomnia, nightmares, weakness, drowsiness, irritability, malaise, lethargy Agitation, confusion, delirium, dysphasia, myoclonus, nystagmus, toxic psychosis. . Gastrointestinal: Painful oral mucosa, oral candidiasis, dysphagia, intestinal perforation, gastrointestinal bleeding. Cholestatic jaundice has been reported. Ileus, jaundice, gastrointestinal bleeding, C. difficile-associated diarrhea, pseudomembranous colitis, pancreatitis, hepatic necrosis, intestinal perforation, dyspepsia, epigastric or abdominal pain, vomiting, constipation, oral ulceration, oral candidiasis, mouth dryness, anorexia, dysphagia, flatulence Constipation, dyspepsia, flatulence, hepatic necrosis, jaundice, pancreatitis, pseudomembranous colitis. (The onset of pseudomembranous colitis symptoms may occur during or after antimicrobial treatment.)

Hemic/Lymphatic: Agranulocytosis, hemolytic anemia, methemaglobinemia, prolongation of prothrombin time

Metabolic/Nutritional: Elevation of serum triglycerides, cholesterol, blood glucose, serum potassium.

Musculoskeletal: Arthralgia or back pain, joint stiffness, achiness, neck or chest pain, flare up of gout. Arthralgia, jaw, arm or back pain, joint stiffness, neck and chest pain, achiness, flare up of gout Myalgia, possible exacerbation of myasthenia gravis, tendinitis/tendon rupture.

Renal/Urogenital: Interstitial nephritis, nephritis, renal failure, polyuria, urinary retention, urethral bleeding, vaginitis, acidosis. Renal failure, intarstitial nephritis, hemorrhagic cystitis, renal calcuti, frequent urination, acidosis, urethral bleeding, polyuria, urinary retention, gynecomastia, candiduria, vaginitis. Crystalluria, cylindruria, hematuria, and albuminutia have also been reported. Albuminuria, candiduria, renal calculi, vaginal candidiasis.

Respiratory: Dyspnea, epistaxis, laryngeal or pulmonary edema, hiccough, hemophysis, bronchospasm, pulmonary embolism. Respiratory arrest, pulmonary embolism, dyspnea, pulmonary edema, respiratory distress, pleural effusion, hemoptysis, epistaxis, hiccough

Skin/Hypersensitivity: Pruritus, urticaria, photosensitivity, flushing, fever, chills, angioedema, edema of the face, neck, lips, conjunctivae or hands, cutaneous candidiasis, hyperpigmentation, erytherna nodosum. Allergic reactions ranging from urticaria to anaphylactic reactions have been reported. Anaphylactic reactions, erythema multiforme/Stevens-Johnson syndrome, exfoliative dermatitis, toxic epidermal necrolysis, vasculitis, angioedema, edema of the lips, face, neck, conjunctivae, hands or lower extremities, purpura, fever, chills, flushing, pruritus, urtigaria, cutaneous candidiasis, vesicles, increased perspiration, hyperpigmentation, erythema nodosum, photosensitivity. Allergic reactions ranging from urticaria to anaphylactic reactions have been reported. Anaphylactic reactions, erythema multiforme/Stevens-Johnson syndrome, exfoliative dermatitis, toxic epidermal necrolysis.

Special Senses: Blurred vision, disturbed vision (change in color perception, overbrightness of lights), decreased visual acuity, diplopia, eye pain, tinnitus, hearing loss, bad taste. Decreased visual acuity, blurred vision, disturbed vision (flashing lights, change in color perception, overbrightness of lights, diplopia), eye pain, anosmia, hearing loss, tinnitus, nystagmus, a bad taste Also reported were agranulocytosis, prolongation of prothrombin time, and possible exacerbation of myasthenia gravis. Anosmia, taste loss.

References

Salahudeen,Meharunnisa etal.,

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.