Moxifloxacin
Systematic (IUPAC) name
1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo [4.3.0]non-8-yl]-6-fluoro-8-methoxy-4-oxo- quinoline-3-carboxylic acid Image File history File links Moxifloxacin. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ...
Identifiers
CAS number	354812-41-2
ATC code	J01MA14
PubChem	152946
DrugBank	APRD00281
Chemical data
Formula	C21H24N3FO4
Mol. weight	401.431 g/mol
Pharmacokinetic data
Bioavailability	86 to 92%
Protein binding	30 to 50%
Metabolism	Glucuronide and sulfate conjugation Cytochrome P450 system not involved
Half life	12 hours
Excretion	Biliary and renal
Therapeutic considerations
Pregnancy cat.	C (US) B3 (Australia) CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance Yellowish brown gas Atomic mass 18. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... BIC pen cap, about 1 gram. ... The mole and its simple conversions into different units of measurements. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Many drugs are bound to Blood plasma proteins. ... Metabolism (from Greek μεταβολισμός metabolismos) is the biochemical modification of chemical compounds in living organisms and cells. ... Glucuronide is a substance produced by attaching glucuronic acid to another substance with glycosidic bonds. ... In inorganic chemistry, a sulfate (IUPAC-recommended spelling; also sulphate in British English) is a salt of sulfuric acid. ... Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... The hour (symbol: h) is a unit of time. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... 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 pregnancy. ... United States is the current Good Article Collaboration of the week! Please help to improve this article to the highest of standards. ...
Legal status	Prescription Only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... A prescription drug (or POM Prescription Only Medicine, in UK) is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ...
Routes	Oral, IV, local (eyedrops)

Moxifloxacin is a synthetic fluoroquinolone antibiotic agent. Bayer AG developed the drug (initially called BAY 12-8039) and it is marketed worldwide (as the hydrochloride) under the brand name Avelox® (in some countries also Avalox®) for oral treatment. Each tablet contains 400mg. In most countries the drug is also available in parenteral form for intravenous infusion. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Quinolones and fluoroquinolones form a group of broad-spectrum antibiotics. ... Staphylococcus aureus - Antibiotics Test plate. ... Bayers logo: the Bayer cross Bayer AG (German pronunciation BYE-er, in US usually pronounced BAY-er) (TYO: 4863) is a German chemical and pharmaceutical company founded in 1863. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ...

Mode of action

Moxifloxacin inhibits bacterial topoisomerase II (DNA gyrase) and topoisomerase IV. Topoisomerases are essential enzymes which play a crucial role in the replication and repair of bacterial DNA. This mechanism is lethal to susceptible bacteria. Moxifloxacin is often referred to as a chemotherapeutic drug because its mode of action has so far not been noted in any natural occurring or semi-synthetic antibiotic.

Distribution

Moxifloxacin is found in high concentrations in body tissues and fluids, such as saliva, nasal and bronchial secretions, sinus mucosa, skin blister fluid, subcutaneous and intraocular tissues. There is good penetration into bone.^[1] Pus does not seem to inhibit the drug's potential to reach effective concentrations in infectious foci easily.

Susceptible bacteria

A broad spectrum of bacteria is susceptible including, but not limited to:

• Staphylococcus aureus
• Staphylococcus epidermidis
• Streptococcus pneumoniae
• Haemophilus influenzae
• Klebsiella spp.
• Moraxella catarrhalis
• Enterobacter spp.
• Mycobacterium spp.
• Bacillus anthracis

Binomial name Staphylococcus aureus Rosenbach 1884 Staphylococcus aureus is a bacterium, frequently living on the skin or in the nose of a healthy person, that can cause illnesses ranging from minor skin infections (such as pimples, boils, and cellulitis) and abscesses, to life-threatening diseases such as pneumonia, meningitis, endocarditis... Binomial name Staphylococcus epidermidis (Winslow & Winslow 1908) Evans 1916 Staphylococcus epidermidis is a member of the bacterial genus Staphylococcus, consisting of Gram-positive cocci arranged in clusters. ... Binomial name Streptococcus pneumoniae (Klein 1884) Chester 1901 Streptococcus pneumoniae is a species of Streptococcus that is a major human pathogen. ... Binomial name Haemophilus influenzae (Lehmann & Neumann 1896) Winslow 1917 Haemophilus influenzae, formerly called Pfeiffers bacillus or Bacillus influenzae, is a non-motile Gram-negative coccobacillus first described in 1892 by Dr. Richard Pfeiffer during an influenza pandemic. ... Klebsiella pneumoniae is a gram-negative rod-shaped bacteria, and clinically the most important member of the Klebsiella genus of Enterobacteriaceae. ... Moraxella catarrhalis is a gram-negative, aerobic, oxidase-positive diplococcus. ... Species etc. ... Species See text. ... Binomial name Bacillus anthracis Cohn 1872 Bacillus anthracis is a Gram-positive, facultatively anaerobic, rod-shaped bacterium of the genus Bacillus. ...

Pharmacokinetic behaviour in patients with decreased liver and renal function

Mild, moderate and severe renal dysfunction does not alter half-life, metabolization or excretion significantly. The same is true to for mild to moderate liver impairment (Child-Pugh class A and B). Nothing is known about severe liver impairment (Child-Pugh class C). The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... In medicine (gastroenterology), the Child_Pugh score (sometimes the Child_Turcotte_Pugh score) is used to assess the prognosis of chronic liver disease, mainly cirrhosis. ...

Uses

Moxifloxacin can be used to treat respiratory infections including acute sinusitis, acute exacerbations of chronic bronchitis and community-acquired pneumonia as well as skin and skin structure infections. Moxifloxacin is also used for the treatment of complicated intra-abdominal infections, as seen in hospitals. Since moxifloxacin is primarily metabolized and eliminate via the hepatic route, moxifloxacin is not indicated for the treatment of urinary tract infections. Sinusitis is inflammation of the paranasal sinuses from either bacterial, fungal, viral, allergic or autoimmune issues. ... This article is not about asthma. ... Pneumonia. ...

Moxifloxacin is used as a second-line agent in tuberculosis and may potentially have benefits in reducing treatment duration from its current six month to four months.^[2] The standard short course treatment for tuberculosis (TB) is isoniazid, rifampicin, pyrazinamide and ethambutol for two months, then isoniazid and rifampicin alone for a further four months. ...

In ophthalmology, moxifloxacin is available the form of eye drops, marketed by Alcon as Vigamox®, to treat conjunctival infections caused by susceptible bacteria. This article or section does not cite its references or sources. ... Eye Drops was a television program on TechTV that showcased short computer animation movies and clips made using off the shelf 3D animation software. ... Alcon, (NYSE: ACL) headquartered in Hünenberg, Switzerland, is a global medical company specializing in eye care products. ... The conjunctiva is a membrane that covers the sclera (white part of the eye) and lines the inside of the eyelids. ...

Resistance

Resistance to moxifloxacin arises in Mycobacterium tuberculosis if moxifloxacin is used alone instead of in combination with other anti-TB drugs,^[3] and this appears to be the explanation for the appearance of moxifloxacin resistance in newly diagnosed TB patients in Baltimore^[4] and in Taiwan.^[5] Worryingly, the development of resistance can appear in as short a time as seven days.^[5] This calls into question the first line use of moxifloxacin and other respiratory quinolones first line for the treatment of community-acquired pneumonia in populations where TB is still endemic.

Dosage

The dosage is 400 mg daily orally or via intravenous infusion (1 hour). The duration of treatment depends on the disease and ranges from 5 days in acute exacerbations of chronic bronchitis to 60 days for post-exposure prophylaxis of anthrax. The bioavailablity of moxifloxacin is over 90%^[6] and therefore there are no advantages to using intravenous moxifloxacin when the patient is able to swallow tablets. The intravenous preparation is not licensed for use in the UK. The milligram (symbol mg) is an SI unit of mass. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Bronchitis is an inflammation of the bronchi of the lungs, that causes the cilia of the bronchial epithelial cells to stop functioning. ...

There is no sufficient clinical data about dosage to patients under 18 years of age. In geriatric patients no dose reductions are necessary. Geriatrics is the branch of medicine that focuses on health promotion and the prevention and treatment of disease and disability in later life. ...

Contraindications

• Known hypersensitivity to moxifloxacin,other quinolones, or any other ingredient of the preparation.
• Patients with history of tendon disorder related to quinolone treatment
• Documented QT prolongation

Hypersensitivity is an immune response that damages the bodys own tissues. ...

Pregnancy and lactation

• Pregnancy : Moxifloxacin has been assigned to class C.
• Lactation : Moxifloxacin is found in high concentration in the milk of breastfeeding mothers. Either the drug or the breastfeeding should be discontinued.

A glass of cows milk Milk is the nutrient fluid produced by the mammary glands of female mammals (including monotremes). ... Wean redirects here: see #Weaning. ...

Side effects

Possible side effects include gastrointestinal tract disturbances (nausea, vomiting, anorexia, bloating, abdominal pain, diarrhea, and pseudomembranous colitis caused by Clostridium difficile), skin reactions (also Stevens-Johnson syndrome), rhabdomyolysis, and serious heart problems (prolonged QT interval and torsades de pointes). Development of resistance has been noticed as well as rare cases of hepatotoxicity and seizures. Tendon rupture (including rupture of the Achilles tendon) can also occur. The gastrointestinal tract or digestive tract, also referred to as the GI tract or the alimentary canal, (nourishment canal) or the gut, is the system of organs within multicellular animals which takes in food, digests it to extract energy and nutrients, and expels the remaining waste. ... For other uses, see Nausea (disambiguation). ... Vomiting (or emesis) is the forceful expulsion of the contents of ones stomach through the mouth. ... Anorexia (deriving from the Greek α(ν)- (a(n)-, a prefix that denotes absence) + όρεξη (orexe) = appetite) is the decreased sensation of appetite. ... Bloating is any abnormal general swelling, or increase in diameter of the abdominal area. ... Diarrhea or diarrhoea (see American and British English spelling differences) is a condition in which the sufferer has frequent watery, loose bowel movements (from the ancient Greek word διαρροή = leakage; literally meaning to run through). Acute infectious diarrhea is a common cause of death in developing countries (particularly among infants), accounting... Pseudomembranous colitis is a infection of the colon caused by the bacterium Clostridium difficile. ... Binomial name Clostridium difficile Hall & OToole, 1935 Clostridium difficile ( ) (also referred to as C. diff or C-diff) is a species of bacteria of the genus Clostridium which are Gram-positive, anaerobic, spore-forming rods. ... Stevens-Johnson syndrome (SJS) is a severe and potentially life-threatening (15% of cases) disease, it is a hypersensitivity complex affecting the skin and the mucous membranes, a severe expression of erythema multiforme (EM) (and so SJS is also called erythema multiforme major). ... Rhabdomyolysis is the breakdown of skeletal muscle due to injury, either mechanical, physical or chemical. ... In medicine, specifically cardiology, the study of the heart, the QT interval is a measure of the time between the start of the Q wave and the end of the T wave in the hearts electrical cycle. ... Torsades de pointes is a medical condition, the name of which means in French twisting of the points. It is a potentially deadly form of ventricular tachycardia. ... Antibiotic resistance is the ability of a microorganism to withstand the effects of an antibiotic. ... Hepatotoxicity (from hepatic toxicity) is chemical-driven liver damage. ... This article is about the medical term, epileptic seizure, as distinct from psychogenic non-epileptic seizure. ... A tendon (or sinew) is a tough band of fibrous connective tissue that connects muscle to bone, or muscle to muscle. ... Posterior view of the foot and leg, showing the Achilles tendon (tendo calcaneus). ...

Moxifloxacin may have a much higher attack rate of Clostridium difficile than other respiratory quinolones, such as levofloxacin.^[7] Levofloxacin is relatively new fluoroquinolone antibiotic, marketed by Ortho-McNeil under the brand name Levaquin. ...

Interactions

Antacids containing aluminium or magnesium ions inhibit the absorption of moxifloxacin. Drugs that prolong the QT interval (e.g. pimozide) may have an additive effect on QT prolongation and lead to increased risk of ventricular arrhythmias. The INR (International Normalised Ratio) may be increased or decreased in patients treated with warfarin. A precautionary measure would be to monitor the INR more closely and, if necessary, adjust the anticoagulant dose as necessary. General Name, Symbol, Number aluminium, Al, 13 Chemical series poor metals Group, Period, Block 13, 3, p Appearance silvery Atomic mass 26. ... General Name, Symbol, Number magnesium, Mg, 12 Chemical series alkaline earth metals Group, Period, Block 2, 3, s Appearance silvery white Atomic mass 24. ... An ion is an atom or group of atoms that normally are electrically neutral and achieve their status as an ion by loss (or addition) of an electron(s). ... In medicine, specifically cardiology, the study of the heart, the QT interval is a measure of the time between the start of the Q wave and the end of the T wave in the hearts electrical cycle. ... Pimozide (sold as Orap®) is an antipsychotic drug. ... Warfarin (also known under the brand names of Coumadin®, Jantoven®, Marevan®, and Waran®) is an anticoagulant medication that is administered orally or, very rarely, by injection. ...

Unlike ciprofloxacin, moxifloxacin has no interactions with warfarin or theophylline. Ciprofloxacin is the generic international name for the synthetic antibiotic manufactured and sold by Bayer Pharmaceutical under the brand names Cipro and Ciproxin (and other brand names in other markets, e. ...

Information for Patients/'non-specialized people'

This section provides information for patients treated with moxifloxacin or those people 'non-specialized' but interested in medicine/pharmacology:

Moxifloxacin (brand names Avelox®, Avalox®, or Vigamox® (eyedrops) for treating local infections of the eyes such as conjunctivitis) is a broad spectrum antibiotic belonging to the fluoroquinolone class. Moxifloxacin is particular active and is therefore used to treat serious infections of the respiratory tract (sinusitis, acute flares of chronical bronichitis, coummunity acquired pneumonia). Other indications are severe infections of the skin or skin-structure, complicated intraabdominal infections, whether related to surgery or not. The drug may also be used to treat tuberculosis as part of a multidrug regime, particular if the disease is resistant to first-line agents. An additional indication is exposure to anthrax bacteria or clincally evident anthrax-disease.

The treatment duration is normally five to 7 days but may be up to 60 days in patients with anthrax-infection. The usual dosage is 400mg daily in a single dose. Commonly, the oral form (tablet) is used, but i.v. treatment is also possible, particular in a hospital setting.

Please consider that moxifloxacin may have a variety of side-effects, but it has been precribed because your type of infection is regarded serious and warrants treatment with a potent drug such as moxifloxacin. Most common side-effects are gastrointestinal reactions (nausea, vomiting, anorexia, bloating, abdominal pain, diarrhoea, and the serious condition pseudomembranous colitis marked by severe, sometimes bloody, diarrhea. Skin reactions can occur and may vary from mild and common (skin rash) to very rare and life-threatening (Stevens-Johnson syndrome). Central nervous system reactions are nervousness, sleeplessness, confusion, and rarely psychotic symptoms or seizures. These clinically relevant symptoms are reversible upon discontinuation of the drug. Rarely severe arrhythmias and tendon ruptures are encountered.

If you experience more than mild side-effects, please do not terminate treatment on your own initiative, but discuss your concerns with a doctor. If you discontinue the drug too early your infection may reoccur and may even be fatal.

In case that you are either pregnant or breast-feeding discuss treatment with your doctor.

Please do not take moxifloaxacin together with antacids, but wait a few hours, because the uptake of moxifloxacin in the body can be blocked. There are some other interactions that your doctor will have checked these before prescribing moxifloxacin.

Trade names

• US: Avelox® (marketed by Schering-Plough)
• UK: Avelox® (no intravenous preparation available)

Schering-Plough Corporation is a pharmaceutical company started in Germany by Ernst Schering in 1851. ...

References

1. ^ Malincarne L, Ghebregzabher M, Moretti M, et al. (2006). "Penetration of moxifloxacin into bone in patients undergoing total knee arthroplasty". J Antimicrob Chemother 57 (5): 950–4. DOI:10.1093/jac/dkl091.
2. ^ Nuermberger EL, Yoshimatsu T, Tyagi S, et al. (2004). "Moxifloxacin-containing regimens of reduced duration produce a stable cure in murine tuberculosis". Am J Resp Crit Care Med 170: 1131–34. DOI:10.1164/rccm.200407-885OC.
3. ^ Ginsburg AS, Sun R, Calamita H, et al. (2005). "Emergence of fluoroquinolone resistance in Mycobacterium tuberculosis during contrinuously dosed mocifloxacin monotherapy in a mouse model". Antimicrob Agents Chemother 49 (9): 3977–79. DOI:10.1128/AAC.49.9.3977-3979.2005.
4. ^ Ginsburg AS, Hooper N, Parrish N, et al. (2003). "Fluoroquinolone resistance in patients with newly diagnosed tuberculosis". Clin Infect Dis 37: 1448–52. PMID 14614666.
5. ^ ^a b Wang J-Y, Hsueh P-R, Jan I-S, et al. (2006). "Empirical treatment with a fluoroquinolone delays the treatment for tuberculosis and is associated with a poor prognosis in endemic areas". Thorax 61: 903–8. DOI:10.1136/thx.2005.056887.
6. ^ Ballow C, Lettieri J, Agarwal V, et al. (1997). "Absolute bioavailability of moxifloxacin". DOI:10.1016/S0149-2918(00)88306-X.
7. ^ von Baum M, Sigge A, Bommer M, et al. (2006). "Moxifloxacin prophylaxis in neutropenic patients". J Antimicrob Chemother 58 (4): 891–94. DOI:10.1093/jac/dkl320.

A digital object identifier (or DOI) is a permanent identifier (permalink) given to a World Wide Web file or other Internet document so that if its Internet address changes, users will be redirected to its new address. ... A digital object identifier (or DOI) is a permanent identifier (permalink) given to a World Wide Web file or other Internet document so that if its Internet address changes, users will be redirected to its new address. ... A digital object identifier (or DOI) is a permanent identifier (permalink) given to a World Wide Web file or other Internet document so that if its Internet address changes, users will be redirected to its new address. ... A digital object identifier (or DOI) is a permanent identifier (permalink) given to a World Wide Web file or other Internet document so that if its Internet address changes, users will be redirected to its new address. ... A digital object identifier (or DOI) is a permanent identifier (permalink) given to a World Wide Web file or other Internet document so that if its Internet address changes, users will be redirected to its new address. ... A digital object identifier (or DOI) is a permanent identifier (permalink) given to a World Wide Web file or other Internet document so that if its Internet address changes, users will be redirected to its new address. ...