Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H20FN3O4 |
Molecular Weight | 337.3461 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC=C(N3CCOCC3)C(F)=C2
InChI
InChIKey=TYZROVQLWOKYKF-ZDUSSCGKSA-N
InChI=1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021130s030,021131s029,021132s034lbl.pdfCurator's Comment: description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc3e3ea4-50aa-49ee-a8bc-fb48bfc8e014
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021130s030,021131s029,021132s034lbl.pdf
Curator's Comment: description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc3e3ea4-50aa-49ee-a8bc-fb48bfc8e014
Linezolid is an antibiotic used for the treatment of infections caused by Gram-positive bacteria that are resistant to other antibiotics. Linezolid appears to be unique in that it blocks the initiation of protein production. Most common adverse reactions include diarrhea, vomiting, headache, nausea, and anemia. Linezolid has the potential for interaction with adrenergic and serotonergic agents. And with monoamine oxidase inhibitors because it’s nonselective inhibitor of monoamine oxidase.
CNS Activity
Originator
Sources: http://www.google.com/patents/WO1995007271A1?cl=en
Curator's Comment: Linezolid was discovered in the 1990s by a team at Pharmacia and Upjohn Company. http://www.google.com/patents/US5688792
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2363853 |
116.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | ZYVOX Approved UseZYVOX is indicated for the treatment of Nosocomial pneumonia caused by Staphylococcus aureus (methicillin-susceptible and -resistant isolates) or Streptococcus pneumoniae. Launch Date2000 |
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Curative | ZYVOX Approved UseZYVOX is indicated for the treatment of Community-acquired pneumonia caused by Streptococcus pneumoniae, including cases with concurrent bacteremia, or Staphylococcus aureus (methicillin-susceptible isolates only). Launch Date2000 |
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Curative | ZYVOX Approved UseZYVOX is indicated for the treatment of Complicated skin and skin structure infections, including diabetic foot infections, without concomitant osteomyelitis, caused by Staphylococcus aureus (methicillin-susceptible and -resistant isolates), Streptococcus pyogenes, or Streptococcus agalactiae. Launch Date2000 |
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Curative | ZYVOX Approved UseZYVOX is indicated for the treatment of infections Vancomycin-resistant Enterococcus faecium infections, including cases with concurrent bacteremia. Launch Date2000 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
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yes |
PubMed
Title | Date | PubMed |
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Oxazolidinones: a review. | 2000 Jan |
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[Methicillin-resistant Staphylococcus aureus--the pathogen]. | 2001 |
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The oxazolidinones as a new family of antimicrobial agent. | 2001 |
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Quinupristin/dalfopristin and linezolid: spectrum of activity and potential roles in therapy--a status report. | 2001 |
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Linezolid absolute bioavailability and the effect of food on oral bioavailability. | 2001 Apr |
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Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents. 3. Synthesis and evaluation of 5-thiocarbamate oxazolidinones. | 2001 Apr |
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Antimicrobial management strategies for Gram-positive bacterial resistance in the intensive care unit. | 2001 Apr |
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Hematologic effects of antimicrobials: focus on the oxazolidinone linezolid. | 2001 Aug |
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Antimicrobial activity of linezolid against Gram-positive cocci isolated in Brazil. | 2001 Aug |
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In vitro antimicrobial activity of GAR-936 tested against antibiotic-resistant gram-positive blood stream infection isolates and strains producing extended-spectrum beta-lactamases. | 2001 Aug |
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New anti-Gram-positive agents. | 2001 Aug |
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Pharmacokinetics, metabolism, and excretion of linezolid following an oral dose of [(14)C]linezolid to healthy human subjects. | 2001 Aug |
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Vancomycin-resistant Enterococcus faecium meningitis successfully managed with linezolid: case report and review of the literature. | 2001 Aug 15 |
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Pneumonia and sepsis due to fluoroquinolone-resistant Capnocytophaga gingivalis after autologous stem cell transplantation. | 2001 Dec |
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Successful treatment of vancomycin-resistant enterococcus meningitis with linezolid: case report and review of the literature. | 2001 Dec |
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Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria. | 2001 Dec |
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Oxazolidinone antibiotics. | 2001 Dec 8 |
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Linezolid therapy of vancomycin-resistant Enterococcus faecium experimental endocarditis. | 2001 Feb |
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In vitro activity of linezolid against multiply resistant Gram-positive clinical isolates. | 2001 Jan |
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Ciprofloxacin- and methicillin-resistant staphylococcus aureus susceptible to moxifloxacin, levofloxacin, teicoplanin, vancomycin and linezolid. | 2001 Jul |
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Linezolid for gram-positive infections. | 2001 Jul |
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[Ribosomal antibiotics]. | 2001 Jul-Aug |
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What do the new antimicrobials offer? Weighing the advantages and disadvantages compared with traditional agents. | 2001 Mar |
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Compatibility of linezolid injection with intravenous administration sets. | 2001 Mar-Apr |
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Linezolid breakpoints. | 2001 May |
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Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine. | 2001 May |
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Linezolid for the treatment of resistant gram-positive cocci. | 2001 May |
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Cardiovascular sympathomimetic amine interactions in rats treated with monoamine oxidase inhibitors and the novel oxazolidinone antibiotic linezolid. | 2001 May |
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Successful treatment of vancomycin-resistant Enterococcus endocarditis with oral linezolid. | 2001 May 1 |
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Linezolid: a new antibiotic for gram-positive infections. | 2001 Nov |
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Pharmacodynamics of antiinfective therapy: taking what we know to the patient's bedside. | 2001 Nov |
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A simple, isocratic high-performance liquid chromatography assay for linezolid in human serum. | 2001 Nov |
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NCCN: Fever and neutropenia. | 2001 Nov-Dec |
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In vitro antimicrobial activity of linezolid tested against vancomycin-resistant enterococci isolated in Brazilian hospitals. | 2001 Oct |
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Oxazolidinones: a new class of antibacterials. | 2001 Oct |
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Activity of linezolid against levofloxacin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci in Hong Kong. | 2001 Oct |
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Successful treatment of disseminated Mycobacterium chelonae infection with linezolid. | 2001 Oct 15 |
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Frequency of isolation and antimicrobial resistance of gram-negative and gram-positive bacteria from patients in intensive care units of 25 European university hospitals participating in the European arm of the SENTRY Antimicrobial Surveillance Program 1997-1998. | 2001 Sep |
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In vitro activity of linezolid against Gram-positive uropathogens of hospitalized patients with complicated urinary tract infections. | 2001 Sep |
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Susceptibility testing with linezolid by different methods, in relation to published 'general breakpoints'. | 2001 Sep |
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Treatment options for vancomycin-resistant enterococcal infections. | 2002 |
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Linezolid-resistant Enterococcus faecium isolated from a patient without prior exposure to an oxazolidinone: report from the SENTRY Antimicrobial Surveillance Program. | 2002 Feb |
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In vitro evaluation of AZD2563, a new oxazolidinone, tested against unusual gram-positive species. | 2002 Feb |
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Approaches to analysis of length of hospital stay related to antibiotic therapy in a randomized clinical trial: linezolid versus vancomycin for treatment of known or suspected methicillin-resistant Staphylococcus species infections. | 2002 Feb |
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An investigation of the antimicrobial effects of linezolid on bacterial biofilms utilizing an in vitro pharmacokinetic model. | 2002 Feb |
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[Significance of antibiotic resistance in treatment of soft tissue infections]. | 2002 Jan |
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Linezolid-Induced anemia and thrombocytopenia. | 2002 Jan |
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In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates. | 2002 Mar |
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Successful treatment of methicillin-resistant Staphylococcus aureus pulmonary infection with linezolid in a patient with cystic fibrosis. | 2002 Mar |
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Thrombocytopenia associated with linezolid therapy. | 2002 Mar 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021130s030,021131s029,021132s034lbl.pdf
Curator's Comment: Injection: 600 mg every 12 hours
Linezolid solution is available in 200, 400, 600 mg. Oral suspensions - 100 mg.
600 mg every 12 hours
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17210770
Linezolid was tested against 32 species of uncommonly isolated gram-positive organisms (3,251 strains) by reference MIC methods and found to be highly active (MIC50 range, 0.25 to 2 microg/ml; MIC90 range, 0.25 to 2 microg/ml).
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000007568
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LIVERTOX |
NBK548245
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NDF-RT |
N0000175495
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C258
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QJ01XX08
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J01XX08
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DB00601
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ISQ9I6J12J
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C29158
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190376
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165800-03-3
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C098010
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7478
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Linezolid
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LINEZOLID
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II-7
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ACTIVE MOIETY
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METABOLITE INACTIVE (PARENT)