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Linezolid is an antibiotic used for the treatment of infections caused by Gram-positive bacteria that are resistant to other antibiotics.
When given for short periods, linezolid is a relatively safe antibiotic.
As a protein synthesis inhibitor, linezolid works by suppressing bacterial protein production.
Linezolid was discovered in the mid 1990s and was approved for commercial use in 2000.
Contents
1 Medical uses
1.1 Skin and soft tissue infections
1.2 Pneumonia
1.3 Other
1.3.1 Infections of the central nervous system
1.3.2 Catheter-related infections
1.4 Specific populations
1.5 Spectrum of activity
1.5.1 Gram-negative bacteria
1.5.2 Comparable antibiotics
2 Adverse effects
2.1 Long-term use
3 Interactions
4 Pharmacology
4.1 Pharmacodynamics
4.2 Pharmacokinetics
5 Chemistry
5.1 Synthesis
6 Resistance
6.1 Mechanism
7 History
8 Society and culture
8.1 Economics
8.2 Brand names
9 References
Medical uses
The main use of linezolid is the treatment of severe infections caused by anaerobic Gram-positive bacteria that are resistant to other antibiotics; it should not be used against bacteria that are sensitive to drugs with a narrower spectrum of activity, such as penicillins and cephalosporins. In both the popular press and the scientific literature, linezolid has been called a “reserve antibiotic”—one that should be used sparingly so that it will remain effective as a drug of last resort against potentially intractable infections.
In the United States, the indications for linezolid use approved by the U.S. Food and Drug Administration (FDA) are the treatment of vancomycin-resistant Enterococcus faecium infections, with or without bacterial invasion of the bloodstream ; nosocomial pneumonia (hospital-acquired) and community-acquired pneumonia caused by S. aureus or S. pneumoniae ; complicated skin and skin structure infections (cSSSI) caused by susceptible bacteria, including diabetic foot infection, unless complicated by osteomyelitis (infection of the bone and bone marrow); and uncomplicated skin and soft tissue infections caused by S. pyogenes or S. aureus.
Linezolid appears to be as safe and effective for use in children and newborns as it is in adults.
Skin and soft tissue infections
A large meta-analysis of randomized controlled trials found linezolid to be more effective than glycopeptide antibiotics (such as vancomycin and teicoplanin ) and beta-lactam antibiotics in the treatment of skin and soft tissue infections (SSTIs) caused by Gram-positive bacteria,
In the treatment of diabetic foot infections, linezolid appears to be cheaper and more effective than vancomycin.
Some authors have recommended that combinations of cheaper or more cost-effective drugs (such as co-trimoxazole with rifampicin or clindamycin ) be tried before linezolid in the treatment of SSTIs when susceptibility of the causative organism allows it.
Pneumonia
No significant difference appears in treatment success rates between linezolid, glycopeptides, or appropriate beta-lactam antibiotics in the treatment of pneumonia.
U.S. guidelines recommend either linezolid or vancomycin as the first-line treatment for hospital-acquired (nosocomial) MRSA pneumonia.
Other
This echocardiogram shows vegetations on the tricuspid valve (white arrow) caused by infective endocarditis. The patient received conventional treatment, with ampicillin, imipenem, and glucocorticoids, and recovered fully after heart surgery.
It is traditionally believed that so-called “deep” infections—such as osteomyelitis or infective endocarditis —should be treated with bactericidal antibiotics, not bacteriostatic ones. Nevertheless, preclinical studies were conducted to assess the efficacy of linezolid for these infections,
In combination with other drugs, linezolid has been used to treat tuberculosis.
Linezolid has been studied as an alternative to vancomycin in the treatment of febrile neutropenia in cancer patients when Gram-positive infection is suspected.
Infections of the central nervous system
In animal studies of meningitis caused by Streptococcus pneumoniae, linezolid was found to penetrate well into cerebrospinal fluid, but its effectiveness was inferior to that of other antibiotics.
Catheter-related infections
In March 2007, the FDA reported the results of a randomized, open-label, phase III clinical trial comparing linezolid to vancomycin in the treatment of catheter-related bloodstream infections. Patients treated with vancomycin could be switched to oxacillin or dicloxacillin if the bacteria that caused their infection was found to be susceptible, and patients in both groups (linezolid and vancomycin) could receive specific treatment against Gram-negative bacteria if necessary.
Linezolid was associated with significantly greater mortality than the comparator antibiotics. When data from all participants were pooled, the study found that 21.5% of those given linezolid died, compared to 16% of those not receiving it. The difference was found to be due to the inferiority of linezolid in the treatment of Gram-negative infections alone or mixed Gram-negative/Gram-positive infections. In participants whose infection was due to Gram-positive bacteria alone, linezolid was as safe and effective as vancomycin.
Specific populations
In adults and children over the age of 12, linezolid is usually given every 12 hours, whether orally or intravenously.
Linezolid is in U.S. pregnancy category C, meaning there have been no adequate studies of its safety when used by pregnant women, and although animal studies have shown mild toxicity to the fetus, the benefits of using the drug may outweigh its risks.
Spectrum of activity
Scanning electron micrographs of vancomycin-resistant Enterococcus (top) and methicillin-resistant Staphylococcus aureus (bottom; false colors)
Linezolid is effective against all clinically important Gram-positive bacteria —those whose cell wall contains a thick layer of peptidoglycan and no outer membrane —notably Enterococcus faecium and Enterococcus faecalis (including vancomycin-resistant enterococci ), Staphylococcus aureus (including methicillin-resistant Staphylococcus aureus, MRSA), Streptococcus agalactiae, Streptococcus pneumoniae, Streptococcus pyogenes, the viridans group streptococci, Listeria monocytogenes, and Corynebacterium species (the latter being among the most susceptible to linezolid, with minimum inhibitory concentrations routinely below 0.5 mg/L).
Linezolid is considered bacteriostatic against most organisms—that is, it stops their growth and reproduction without actually killing them—but has some bactericidal (killing) activity against streptococci.
Gram-negative bacteria
Linezolid has no clinically significant effect on most Gram-negative bacteria. Pseudomonas and the Enterobacteriaceae, for instance, are not susceptible.
Comparable antibiotics
Linezolid’s spectrum of activity against Gram-positive bacteria is similar to that of the glycopeptide antibiotic vancomycin, which has long been the standard for treatment of MRSA infections, and the two drugs are often compared.
Adverse effects
When used for short periods, linezolid is a relatively safe drug.
Like nearly all antibiotics, linezolid has been associated with Clostridium difficile -associated diarrhea (CDAD) and pseudomembranous colitis, although the latter is uncommon, occurring in about one in two thousand patients in clinical trials.
Long-term use
Bone marrow suppression, characterized particularly by thrombocytopenia (low platelet count), may occur during linezolid treatment; it appears to be the only adverse effect that occurs significantly more frequently with linezolid than with glycopeptides or beta-lactams.
Long-term use of linezolid has also been associated with chemotherapy-induced peripheral neuropathy, a progressive and enduring often irreversible tingling numbness, intense pain, and hypersensitivity to cold, beginning in the hands and feet and sometimes involving the arms and legs.
The adverse effects of long-term linezolid therapy were first identified during postmarketing surveillance. Bone marrow suppression was not identified during Phase III trials, in which treatment did not exceed 21 days. Although some participants of early trials did experience thrombocytopenia, it was found to be reversible and did not occur significantly more frequently than in controls (participants not taking linezolid).
Interactions
Linezolid is a weak monoamine oxidase inhibitor (MAOI), and should not be used concomitantly with other MAOIs, large amounts of tyramine -rich foods (such as pork, aged cheeses, alcoholic beverages, or smoked and pickled foods), or serotonergic drugs. There have been postmarketing reports of serotonin syndrome when linezolid was given with or soon after the discontinuation of serotonergic drugs, particularly selective serotonin reuptake inhibitors such as paroxetine and sertraline. It should also not be given in combination with pethidine ( meperidine ) under any circumstance due to the risk of serotonin syndrome.
Linezolid does not inhibit or induce the cytochrome P450 (CYP) system, which is responsible for the metabolism of many commonly used drugs, and therefore does not have any CYP-related interactions.
Pharmacology
Pharmacodynamics
Further information: Prokaryotic translation and Translation (genetics) § Basic mechanisms
Simplified schematic of mRNA translation. Linezolid occupies the A site (at center) and prevents tRNA from binding.
Linezolid, like other oxazolidinones, is a bacterial protein synthesis inhibitor and a weak, non-selective, reversible monoamine oxidase inhibitor.
In 2008, the crystal structure of linezolid bound to the 50S subunit of a ribosome from the archaean Haloarcula marismortui was elucidated by a team of scientists from Yale University and deposited in the Protein Data Bank.
Pharmacokinetics
Major metabolites of linezolid
One of the advantages of linezolid is that it has an absolute oral bioavailability of 100% due to its rapid and complete absorption after oral administration ;
Taking linezolid with food somewhat slows its absorption, but the area under the curve is not affected.
Linezolid’s plasma protein binding is approximately 31% (range 4–32% ) and its volume of distribution at steady state averages 36.1–47.3  liters in healthy adult volunteers.
Linezolid is metabolized in the liver, by oxidation of the morpholine ring, without involvement of the cytochrome P450 system. This metabolic pathway leads to two major inactive metabolites (which each account for around 45% and 10% of an excreted dose at steady state), one minor metabolite, and several trace metabolites, none of which accounts for more than 1% of an excreted dose.
Chemistry
At physiological pH (7.4), linezolid exists in an uncharged state. It is moderately water-soluble (approximately 3 mg/mL), with a log P of 0.55.
Numbered structure of linezolid, showing the pharmacophore required for good activity (in blue) and desirable structural features (in orange).
The oxazolidinone pharmacophore —the chemical “template” essential for antimicrobial activity —consists of a 1,3-oxazolidin-2-one moiety with an aryl group at position 3 and an S – methyl group, with another substituent attached to it, at position 5 (the R – enantiomers of all oxazolidinones are devoid of antibiotic properties).
The anticoagulant rivaroxaban (Xarelto) bears a striking structural similarity to linezolid; both drugs share the oxazolidinone pharmacophore, differing in only three areas (an extra ketone and chloro thiophene, and missing the fluorine atom). However this similarity appears to carry no clinical significance.
Synthesis
Linezolid is a completely synthetic drug: it does not occur in nature (unlike erythromycin and many other antibiotics) and was not developed by building upon a naturally occurring skeleton (unlike most beta-lactams, which are semisynthetic ). Many approaches are available for oxazolidinone synthesis, and several routes for the synthesis of linezolid have been reported in the chemistry literature.
Later syntheses have included an ” atom-economical ” method starting from D -mannitol, developed by Indian pharmaceutical company Dr. Reddy’s and reported in 1999,
Resistance
Acquired resistance to linezolid was reported as early as 1999, in two patients with severe, multidrug-resistant Enterococcus faecium infection who received the drug through a compassionate use program.
In the United States, resistance to linezolid has been monitored and tracked since 2004 through a program named LEADER, which (as of 2007
Mechanism
The intrinsic resistance of most Gram-negative bacteria to linezolid is due to the activity of efflux pumps, which actively “pump” linezolid out of the cell faster than it can accumulate.
Gram-positive bacteria usually develop resistance to linezolid as the result of a point mutation known as G2576T, in which a guanine base is replaced with thymine in base pair 2576 of the genes coding for 23S ribosomal RNA.
History
The oxazolidinones have been known as monoamine oxidase inhibitors since the late 1950s. Their antimicrobial properties were discovered by researchers at E.I. duPont de Nemours in the 1970s.
Pharmacia & Upjohn (now part of Pfizer) started its own oxazolidinone research program in the 1990s. Studies of the compounds’ structure–activity relationships led to the development of several subclasses of oxazolidinone derivatives, with varying safety profiles and antimicrobial activity. Two compounds were considered drug candidates: eperezolid (codenamed PNU-100592 ) and linezolid ( PNU-100766 ).
As of 2009
Society and culture
Economics
Further information: Pharmacoeconomics and Disease burden
Linezolid was quite expensive in 2009; a course of treatment may cost one or two thousand U.S. dollars for the drug alone,
However, because intravenous linezolid may be switched to an oral formulation (tablets or oral solution) without jeopardizing efficacy, people may be discharged from hospital relatively early and continue treatment at home, whereas home treatment with injectable antibiotics may be impractical. Reducing the length of hospital stay reduces the overall cost of treatment, even though linezolid may have a higher acquisition cost—that is, it may be more expensive—than comparable antibiotics.
Studies have been conducted in several countries with different health care system models to assess the cost-effectiveness of linezolid compared to glycopeptides such as vancomycin or teicoplanin. In most countries, linezolid was more cost-effective than comparable antibiotics for the treatment of hospital-acquired pneumonia and complicated skin and skin structure infections, either due to higher cure and survival rates or lower overall treatment costs.
In 2009, Pfizer paid $2.3 billion and entered a corporate integrity agreement to settle charges that it had misbranded and illegally promoted four drugs, and caused false claims to be submitted to government healthcare programs for uses that had not been approved by the United States Food and Drug Administration.
Brand names
Linezolid is marketed by Pfizer under the trade names Zyvox (in the United States, United Kingdom, Australia, and several other countries), Zyvoxid (in Europe), and Zyvoxam (in Canada and Mexico). Generics are also available, such as Linezomentin (in Egypt, by Arabcomed), Lenzomore (in India, by Morepen), Linospan (in India, by Cipla ), Nezocin (in Pakistan, by Brookes ), Voxazoldin (in Egypt, by Rotabiogen), Lizomed (in India, as a dry syrup by Aglowmed), and Linzolid (in Bangladesh, by Incepta ).

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