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Levofloxacin
Systematic (IUPAC) name
(-)-(S)-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 100986-85-4
ATC code J01MA12 S01AX19
PubChem 149096
DrugBank APRD00477
Chemical data
Formula C18H20FN3O4 
Mol. mass 361. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Fluorine, fluorum meaning "to flow" is the Chemical element with the symbol F and Atomic number 9 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 368 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 99%
Protein binding 24 to 38%
Metabolism Renal
Half life 6 to 8 hours
Excretion Urinary
Therapeutic considerations
Pregnancy cat.

C (United States)
Legal status

Prescription Only
Routes Oral, IV, Ophthalmic

Levofloxacin is a 3rd generation fluoroquinolone antibiotic, marketed by Ortho-McNeil under the trade name Levaquin in the United States. For other uses of the words gram or gramme see Gram (disambiguation. The mole (symbol mol) is a unit of Amount of substance: it is an SI base unit, and almost the only unit to be used to measure this In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of A drug's efficiency may be affected by the degree to which it binds to the proteins within Blood plasma. Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The kidneys are complicated organs that have numerous biological roles The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity The hour (symbol h) is a unit of Time. It is not an SI unit but is accepted for use with the SI Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during The United States of America —commonly referred to as the The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained In Pharmacology and Toxicology, a route In Pharmacology and Toxicology, a route Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. The quinolones are a family of synthetic Broad-spectrum antibiotics. In modern usage an antibiotic is a Chemotherapeutic agent with activity against Microorganisms such as Bacteria, fungi or Protozoa Ortho-McNeil Pharmaceutical, Inc is a Pharmaceutical manufacturer based in Raritan New Jersey, and a subsidiary of Johnson & Johnson. The United States of America —commonly referred to as the In Europe, it is marketed by Sanofi-Aventis under the trade name Tavanic, in Chile as Gatigol by Alpes Selection, in India under the trade name Lebact marketed by Nicolas Piramal and in Asia it is marketed by Daiichi under the trade names Cravit and Levox. Sanofi-Aventis () headquartered in Paris, France, is a multinational pharmaceutical company ( is a joint Holding company established in 2005 by and, which are Pharmaceutical companies based in Japan. Levofloxacin was launched in the Japanese market in 1993, and thus has had more than 13 years of testing in efficacy and safety globally. Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin, and has approximately twice the potency of ofloxacin, because the R+enantiomer (D-isomer) of ofloxacin is essentially inactive. In Chemistry, an enantiomer ( from the Greek ἐνάντιος opposite and μέρος part or portion is one of two Stereoisomers that are nonsuperimposable This article is about the chemical concept For "isomerism" of atomic nuclei see Nuclear isomer. Ofloxacin (sold under the brand name Floxin in the United States, Tarivid in Europe and some other countries is a Fluoroquinolone Antibiotic In Chemistry, an enantiomer ( from the Greek ἐνάντιος opposite and μέρος part or portion is one of two Stereoisomers that are nonsuperimposable This article is about the chemical concept For "isomerism" of atomic nuclei see Nuclear isomer. Ofloxacin (sold under the brand name Floxin in the United States, Tarivid in Europe and some other countries is a Fluoroquinolone Antibiotic In addition, the S-enantiomer (L-isomer) of ofloxacin, has substantially less toxicity. In Chemistry, an enantiomer ( from the Greek ἐνάντιος opposite and μέρος part or portion is one of two Stereoisomers that are nonsuperimposable This article is about the chemical concept For "isomerism" of atomic nuclei see Nuclear isomer. Ofloxacin (sold under the brand name Floxin in the United States, Tarivid in Europe and some other countries is a Fluoroquinolone Antibiotic Like other fluoroquinolines, it works by inhibiting DNA gyrase, an enzyme that negatively supercoils DNA. DNA gyrase, often referred to simply as gyrase, is a type II Topoisomerase ( that introduces negative Supercoils (or relaxes positive supercoils into DNA

Levofloxacin is effective against a number of gram-positive and gram-negative bacteria. Gram-positive bacteria are those that are stained dark blue or violet by Gram staining. Gram-negative bacteria are those Bacteria that do not retain Crystal violet dye in the Gram staining protocol The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have Because of its broad spectrum of action, levofloxacin is frequently prescribed empirically for a wide range of infections (e. g. pneumonia, urinary tract infection) before the specific causal organism is known. Pneumonia is an inflammatory illness of the Lung. Frequently it is described as lung Parenchyma / alveolar inflammation and abnormal A urinary tract infection ( UTI) is a bacterial Infection that affects any part of the Urinary tract. If the causal organism is identified, levofloxacin may be discontinued and the patient may be switched to an antibiotic with a narrower spectrum of activity. Levofloxacin is currently the only respiratory fluoroquinolone approved by the U. S. FDA for the treatment of nosocomial pneumonia. Hospital-acquired pneumonia (HAP or Nosocomial pneumonia refers to any Pneumonia contracted within 48-72 hours of being admitted in hospital

Contents

Susceptible organisms

Gram-positive bacteria

Gram-negative bacteria

Side Effects

This drug has similar side effects to all the other fluoroquinolone antibiotics. Enterococcus faecalis – formerly classified as part of the Group D Streptococcus system – is a Gram-positive Commensal Bacterium Staphylococcus aureus (ˌstæfɨləˈkɒkəs ˈɔriəs literally "Golden Cluster Seed" and also known as golden staph) is the most common cause of Meticillin ( INN, BAN) or methicillin ( USAN) is a narrow spectrum Beta-lactam antibiotic of the Penicillin class Staphylococcus epidermidis is a member of the bacterial genus Staphylococcus, consisting of Gram-positive cocci arranged in clusters Meticillin ( INN, BAN) or methicillin ( USAN) is a narrow spectrum Beta-lactam antibiotic of the Penicillin class Staphylococcus saprophyticus is a Coagulase -negative species of Staphylococcus bacteria Streptococcus pneumoniae, or pneumococcus, is a Gram-positive, alpha-hemolytic diplococcus aerotolerant anaerobe and a member of the Genus Streptococcus pyogenes is a spherical Gram-positive Bacteria that grows in long chains and is the cause of Group A streptococcal infections Enterobacter is a genus of common Gram-negative, facultatively-anaerobic, rod-shaped Bacteria of the family Enterobacteriaceae Klebsiella pneumoniae is a Gram-negative, non- Motile, Encapsulated, Lactose fermenting, Facultative anaerobic Pseudomonas aeruginosa is a Gram-negative, aerobic, rod-shaped Bacterium with unipolar motility. Legionella pneumophila is a thin pleomorphic, Flagellated Gram-negative bacterium of the genus Legionella. Serratia marcescens is a species of Gram-negative Bacterium in the family Enterobacteriaceae. Haemophilus influenzae, formerly called Pfeiffer's bacillus or Bacillus influenzae, is a non-motile Gram-negative Coccobacillus Moraxella catarrhalis is a Gram-negative, Aerobic, oxidase-positive Diplococcus which may both colonize and cause Respiratory Proteus mirabilis is a Gram-negative, facultatively anaerobic Bacterium. The Genus Campylobacter, (meaning 'twisted bacteria' first discovered in 1963 describes Gram-negative, spiral Microaerophilic bacteria

As with all fluoroquinolones there are numerous documented cases of spontaneous tendon rupture (Maurin, 2008; Mehlhorn & Brown, 2007; Ng & Naughton, 2007; Salvi, 2007). 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 life long 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 Pyschosis has also been reported.

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

In 2004 new warning labels were 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.

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 Levaquin 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. paranoia, toxic psychosis, dysphasia, phobia, unresponsiveness, confusion, anxiety, agitation, delirium, myoclonus, nystagmus.

Gastrointestinal: Painful oral mucosa, oral candidiasis, dysphagia, intestinal perforation, gastrointestinal bleeding. Cholestatic jaundice has been reported. Ileus, jaundice, C. difficle associated diarrhea, pseudomembranous colitis, pancreatitis, hepatic necrosis, dyspepsia, epigastric or abdominal pain, vomiting, constipation, oral ulceration, mouth dryness, anorexia, flatulence. Constipation, dyspepsia. (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, hemorrhagic cystitis, renal calcuti, frequent urination, polyuria, urinary retention, gynecomastia, candiduria. Crystalluria, cylindruria, hematuria, and albuminutia have also been reported. Albuminuria, vaginal candidiasis.

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

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, 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.

Adverse Laboratory Changes include:

Hepatic: Elevations of ALT (SGPT), AST (SGOT), alkaline phosphatase, LDH, serum bilirubin. Hematologic: Eosinophilia, leukopenia, decreased blood platelets, elevated blood platelets, pancytopenia.

Renal: Elevations of serum creatinine, BUN, CRYSTALLURIA, CYLINDRURIA, AND HEMATURIA HAVE BEEN REPORTED.

Other Changes: Elevation of serum gammaglutamyl transferase, elevation of serum amylase, reduction in blood glucose, elevated uric acid, decrease in hemoglobin, anemia, bleeding diathesis, increase in blood monocytes, leukocytosis.


Other

External Link

http://www.bangladesh-drug-medicine.info/wiki/Ovel-500

References

http://www.jabfm.org/cgi/content/full/16/5/458 http://jac.oxfordjournals.org/cgi/content/full/51/3/747

http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.DrugDetails

http://www.fqresearch.org

Maurin N. Mycoplasma pneumoniae is a very small Bacterium in the class Mollicutes. Peptostreptococcus is a Genus of anaerobic, Gram-positive, non- spore forming bacteria. , Fluoroquinolone-induced Achilles tendon rupture, Deutsche medizinische Wochenschrift (1946) (0012-0472) 2008 Feb. Vol. 133,Iss. 6;p. 241-4

Mehlhorn AJ; Brown DA. , Safety concerns with fluoroquinolones, The Annals of pharmacotherapy (1060-0280), 2007 Nov. Vol. 41,Iss. 11;p. 1859-66

Ng WF; Naughton M. , Fluoroquinolone-associated tendinopathy: a case report. Journal of medical case reports 2007 Jul 23. Vol. 1;p. 55

Salvi, A. E. , Spontaneous bilateral Achilles tendon rupture in a patient treated with oral levofloxacin, Journal of Orthopaedics and Traumatology (1590-9921), 1 Jun 2007. Vol. 8, Iss. 2;p. 86(5),

(Cravit)

Dictionary

levofloxacin

-noun

  1. a broad-spectrum antibiotic having a fluoroquinolone structure
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