Linezolid

Identification

Summary

Linezolid is an oxazolidinone antibiotic used to treat infections by susceptible strains of aerobic Gram-positive bacteria.

Brand Names
Zyvox, Zyvoxam
Generic Name
Linezolid
DrugBank Accession Number
DB00601
Background

Linezolid is a synthetic antibiotic which is used for the treatment of infections caused by aerobic Gram-positive bacteria. Its effects are bacteriostatic against both enterococci and staphylococci and bactericidal against most isolates of streptococci.9 Linezolid exerts its antibacterial activity by inhibiting the initiation of bacterial protein synthesis - more specifically, it binds to the 23S ribosomal RNA of the 50S subunit7,8 and, in doing so, prevents the formation of the 70S initiation complex which is essential for bacterial reproduction.

Linezolid was initially approved in 2000 and was the first member of the oxazolidinone antibiotic class.3 A second member of this class, tedizolid, was approved by the FDA in 2014 and is considered generally more effective and tolerable than its predecessor.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 337.3461
Monoisotopic: 337.143784348
Chemical Formula
C16H20FN3O4
Synonyms
  • Linezolid
  • Linezolide
  • Linezolidum
  • N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide
External IDs
  • INF 0026
  • PNU 100766
  • U 100
  • U 100766
  • U 766
  • U-100,766
  • U-100766

Pharmacology

Indication

Linezolid is indicated in adults and children for the treatment of infections caused by susceptible Gram-positive bacteria, including nosocomial pneumonia, community-acquired pneumonia, skin and skin structure infections, and vancomycin-resistant Enterococcus faecium infections.9 Examples of susceptible bacteria include Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes, and Streptococcus agalactiae.9

Linezolid is not indicated for the treatment of Gram-negative infections, nor has it been evaluated for use longer than 28 days.9

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Linezolid is an oxazolidinone antibacterial agent effective against most strains of aerobic Gram-positive bacteria and mycobacteria. It appears to be bacteriostatic against both staphylococci and enterococci and bactericidal against most isolates of streptococci.9 Linezolid has shown some in vitro activity against Gram-negative and anaerobic bacteria but is not considered efficacious against these organisms.9

Linezolid is a reversible and non-selective inhibitor of monoamine oxidase (MAO) enzymes and can therefore contribute to the development of serotonin syndrome when administered alongside serotonergic agents such as selective serotonin re-uptake inhibitors (SSRIs) or tricyclic antidepressants (TCAs).9 Linezolid should not be used for the treatment of catheter-related bloodstream infections or catheter-site infections, as the risk of therapy appears to outweigh its benefits under these circumstances.9

Mechanism of action

Linezolid exerts its antibacterial effects by interfering with bacterial protein translation.2 It binds to a site on the bacterial 23S ribosomal RNA of the 50S subunit and prevents the formation of a functional 70S initiation complex, which is essential for bacterial reproduction, thereby preventing bacteria from dividing.9

Point mutations in the bacterial 23S rRNA can lead to linezolid resistance, and the development of linezolid-resistant Enterococcus faecium and Staphylococcus aureus have been documented during its clinical use.9 As antimicrobial susceptibility patterns are geographically distinct, local antibiograms should be consulted to ensure adequate coverage of relevant pathogens prior to use.

TargetActionsOrganism
A23S ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
Absorption

Linezolid is extensively absorbed following oral administration and has an absolute bioavailability of approximately 100%.9 Maximum plasma concentrations are reached within approximately 1 to 2 hours after dosing (Tmax) and range from 8.1-12.9 mcg/mL after single doses and 11.0-21.2 mcg/mL after multiple dosing.9

The absorption of orally administered linezolid is not significantly affected by co-administration with food and it may therefore be given without regard to the timing of meals.9

Volume of distribution

At steady-state, the volume of distribution of linezolid in healthy adults is approximately 40-50 liters.9

Protein binding

Plasma protein binding of linezolid is approximately 31% - primarily to serum albumin6 - and is concentration-dependent.9

Metabolism

Linezolid is primarily metabolized to two inactive metabolites: an aminoethoxyacetic acid metabolite (PNU-142300) and a hydroxyethyl glycine metabolite (PNU-142586), both of which are the result of morpholine ring oxidation.9,5 The hydroxyethyl glycine metabolite - the most abundant of the two metabolites11 - is likely generated via non-enzymatic processes, though further detail has not been elucidated.9,5

While the specific enzymes responsible for the biotransformation of linezolid are unclear, it does not appear to be subject to metabolism via the CYP450 enzyme system, nor does it meaningfully inhibit or induce these enzymes.11 Linezolid is, however, a reversible and non-selective inhibitor of monoamine oxidase enzymes.9

Hover over products below to view reaction partners

Route of elimination

Urinary excretion is the primary means by which linezolid and its metabolic products are excreted. Following the administration of a radiolabeled dose of linezolid under steady-state conditions, approximately 84% of radioactivity was recovered in the urine,5 of which approximately 30% is unchanged parent drug, 40% is the hydroxyethyl glycine metabolite, and 10% is the aminoethoxyacetic acid metabolite.9 Fecal elimination is comparatively minor, with no parent drug observed in feces and only 6% and 3% of an administered dose found in the feces as the hydroxyethyl glycine metabolite and the aminoethoxyacetic acid metabolite, respectively.9

Half-life

The elimination half-life is estimated to be between 5 and 7 hours.11

Clearance

Total clearance of linezolid is estimated to be 100-200 mL/min, the majority of which appears to be non-renal.11 Mean renal clearance is approximately 40 mL/min, which suggests net tubular reabsorption,9 while non-renal clearance is estimated to account for roughly 65% of total clearance,9 or 70-150 mL/min on average.11 Variability in linezolid clearance is high, particularly for non-renal clearance.11

Adverse Effects
Adverseeffects
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Toxicity

Clinical signs of overdosage observed in rats were decreased activity and ataxia (2000 mg/kg/day) and in dogs were vomiting and tremors (3000 mg/kg/day).9 Treatment of overdose should involve symptomatic and supportive measures and may include hemodialysis if clinically necessary.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe risk or severity of adverse effects can be increased when Linezolid is combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Linezolid is combined with Abciximab.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Linezolid.
AcarboseLinezolid may increase the hypoglycemic activities of Acarbose.
AcebutololThe risk or severity of hypertension can be increased when Linezolid is combined with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Linezolid is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Linezolid is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Linezolid is combined with Acenocoumarol.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Linezolid.
AcetohexamideLinezolid may increase the hypoglycemic activities of Acetohexamide.
Interactions
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Food Interactions
  • Avoid tyramine-containing foods and supplements. Avoid food containing high amounts of tyramine (>100mg). Tyramine-containing foods include cheese, red wine, fava beans, pickled foods, cured foods, and alcoholic beverages.
  • Take with or without food. Co-administration with food does not significantly alter the pharmacokinetics of linezolid.

Products

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Product Images
International/Other Brands
Antizolid (Verisfield) / Linosept (Orion) / Linozid (Orion) / Lizbid (Abbott) / Lizemox (Molekule) / Lizolid (Glenmark) / Xolid (Corona) / Zenix (Hemofarm) / Zizolid (Biofarma) / Zodlin (FDC) / Zolinid (Teva) / Zyvoxid (Pfizer)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LinezolidTablet600 mgOralPanda Pharmaceuticals Inc.Not applicableNot applicableCanada flag
LinezolidInjection, solution2 mg/1mLIntravenousHospira, Inc.2015-06-18Not applicableUS flag
Linezolid InjectionSolution2 mg / mLIntravenousTEVA Canada Limited2014-08-182018-05-17Canada flag
Linezolid InjectionSolution600 mg / 300 mLIntravenousAuro Pharma IncNot applicableNot applicableCanada flag
Linezolid InjectionSolution2 mg / mLIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Linezolid InjectionSolution2 mg / mLIntravenousMda Inc.Not applicableNot applicableCanada flag
Linezolid InjectionSolution2 mg / mLIntravenousJamp Pharma Corporation2019-12-30Not applicableCanada flag
Linezolid InjectionSolution2 mg / mLIntravenousFresenius Kabi2015-06-12Not applicableCanada flag
Linezolid InjectionSolution2 mg / mLIntravenousHospira Healthcare UlcNot applicableNot applicableCanada flag
Linezolid InjectionSolution2 mg / mLIntravenousNeo Health Canada Inc.Not applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-linezolidTablet600 mgOralApotex Corporation2014-08-19Not applicableCanada flag
LinezolidInjection, solution2 mg/1mLIntravenousHospira, Inc.2015-07-072018-07-01US flag
LinezolidTablet, film coated600 mg/1OralMylan Pharmaceuticals Inc.2015-12-212019-05-31US flag
LinezolidTablet, film coated600 mg/1OralMajor Pharmaceuticals2015-12-21Not applicableUS flag
LinezolidInjection, solution600 mg/300mLIntravenousPiramal Critical Care Inc2019-12-18Not applicableUS flag
LinezolidInjection, solution2 mg/1mLIntravenousFresenius Kabi USA, LLC2015-06-22Not applicableUS flag
LinezolidTablet, film coated600 mg/1OralAvPAK2015-12-31Not applicableUS flag
LinezolidInjection, solution200 mg/100mLIntravenousMylan Institutional LLC2018-07-31Not applicableUS flag
LinezolidTablet, film coated600 mg/1OralMylan Institutional Inc.2015-12-162019-05-31US flag
LinezolidInjection, solution200 mg/100mLIntravenousSun Pharmaceutical Industries, Inc.2017-02-01Not applicableUS flag

Categories

ATC Codes
J01XX08 — Linezolid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxazinanes
Sub Class
Morpholines
Direct Parent
Phenylmorpholines
Alternative Parents
Aniline and substituted anilines / Dialkylarylamines / Fluorobenzenes / Oxazolidinones / Aryl fluorides / Acetamides / Carbamate esters / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Dialkyl ethers
show 7 more
Substituents
Acetamide / Amine / Amino acid or derivatives / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbamic acid ester
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, acetamides, morpholines, oxazolidinone (CHEBI:63607)
Affected organisms
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Streptococcus agalactiae
  • Staphylococcus aureus
  • Enterococcus faecalis
  • Staphylococcus epidermidis
  • Enterococcus faecium
  • Streptococcus viridans
  • Staphylococcus haemolyticus
  • Gram positive bacteria

Chemical Identifiers

UNII
ISQ9I6J12J
CAS number
165800-03-3
InChI Key
TYZROVQLWOKYKF-ZDUSSCGKSA-N
InChI
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
IUPAC Name
N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
SMILES
CC(=O)NC[C@H]1CN(C(=O)O1)C1=CC(F)=C(C=C1)N1CCOCC1

References

Synthesis Reference

Brickner SJ, Hutchinson DK, Barbachyn MR, Manninen PR, Ulanowicz DA, Garmon SA, Grega KC, Hendges SK, Toops DS, Ford CW, Zurenko GE: Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections. J Med Chem. 1996 Feb 2;39(3):673-9. doi: 10.1021/jm9509556.

US5688792
General References
  1. Park IN, Hong SB, Oh YM, Kim MN, Lim CM, Lee SD, Koh Y, Kim WS, Kim DS, Kim WD, Shim TS: Efficacy and tolerability of daily-half dose linezolid in patients with intractable multidrug-resistant tuberculosis. J Antimicrob Chemother. 2006 Sep;58(3):701-4. Epub 2006 Jul 19. [Article]
  2. Azzouz A, Preuss CV: Linezolid . [Article]
  3. Leach KL, Brickner SJ, Noe MC, Miller PF: Linezolid, the first oxazolidinone antibacterial agent. Ann N Y Acad Sci. 2011 Mar;1222:49-54. doi: 10.1111/j.1749-6632.2011.05962.x. [Article]
  4. Dryden MS: Linezolid pharmacokinetics and pharmacodynamics in clinical treatment. J Antimicrob Chemother. 2011 May;66 Suppl 4:iv7-iv15. doi: 10.1093/jac/dkr072. [Article]
  5. Slatter JG, Stalker DJ, Feenstra KL, Welshman IR, Bruss JB, Sams JP, Johnson MG, Sanders PE, Hauer MJ, Fagerness PE, Stryd RP, Peng GW, Shobe EM: Pharmacokinetics, metabolism, and excretion of linezolid following an oral dose of [(14)C]linezolid to healthy human subjects. Drug Metab Dispos. 2001 Aug;29(8):1136-45. [Article]
  6. Stalker DJ, Jungbluth GL: Clinical pharmacokinetics of linezolid, a novel oxazolidinone antibacterial. Clin Pharmacokinet. 2003;42(13):1129-40. doi: 10.2165/00003088-200342130-00004. [Article]
  7. Colca JR, McDonald WG, Waldon DJ, Thomasco LM, Gadwood RC, Lund ET, Cavey GS, Mathews WR, Adams LD, Cecil ET, Pearson JD, Bock JH, Mott JE, Shinabarger DL, Xiong L, Mankin AS: Cross-linking in the living cell locates the site of action of oxazolidinone antibiotics. J Biol Chem. 2003 Jun 13;278(24):21972-9. Epub 2003 Apr 10. [Article]
  8. Roger C, Roberts JA, Muller L: Clinical Pharmacokinetics and Pharmacodynamics of Oxazolidinones. Clin Pharmacokinet. 2018 May;57(5):559-575. doi: 10.1007/s40262-017-0601-x. [Article]
  9. FDA Approved Drug Products: Zyvox (linezolid) for intravenous or oral administration [Link]
  10. Health Canada Product Monograph: Linezolid oral tablets [Link]
  11. FDA Pharmacology and Biopharmaceutics Review: Linezolid [Link]
Human Metabolome Database
HMDB0014739
KEGG Drug
D00947
KEGG Compound
C08146
PubChem Compound
441401
PubChem Substance
46504452
ChemSpider
390139
BindingDB
50116067
RxNav
190376
ChEBI
63607
ChEMBL
CHEMBL126
ZINC
ZINC000002008866
Therapeutic Targets Database
DAP000398
PharmGKB
PA450233
PDBe Ligand
ZLD
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Linezolid
PDB Entries
3cpw / 3dll / 4k7q / 4wfa / 5nz0
FDA label
Download (106 KB)
MSDS
Download (43.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDiabetes Mellitus1
4CompletedTreatmentGram Positive Bacterial Infections / Skin and Connective Tissue Diseases1
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA)2
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA) / Skin/Soft Tissue Infections1
4CompletedTreatmentMRSA Infections1
4CompletedTreatmentVentilator Associated Bacterial Pneumonia1
4RecruitingTreatmentCritically Ill Patients / Mechanical Ventilation Complication1
4TerminatedPreventionAcute Bacterial Skin and Skin Structure Infection (ABSSSI) / Bacteremia / Endocarditis / Healthcare-associated Pneumonia (HCAP) / Osteomyelitis/Septic Arthritis1
4Unknown StatusNot AvailablePneumonia1
4Unknown StatusTreatmentBacteremia / Catheter Related Infections1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
  • Fresenius Kabi AB
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Pfizer Inc.
  • Pharmacia Inc.
Dosage Forms
FormRouteStrength
Tablet, film coatedOral600.00 mg
TabletOral
Tablet, film coatedOral
InjectionIntravenous
SolutionIntravenous2 mg
SolutionIntravenous600 mg
TabletOral600 mg
Injection, solutionIntravenous2 mg/1mL
Injection, solutionIntravenous200 mg/100mL
Injection, solutionIntravenous600 mg/300mL
PowderNot applicable1 kg/1kg
Powder, for suspensionOral100 mg/5mL
TabletOral600 mg/1
SolutionParenteral
Injection, solution
SolutionIntravenous600 mg / 300 mL
Injection, solution2 MG/ML
Granule, for solutionOral
Injection, solutionIntravenous
Injection, solutionParenteral2 MG/ML
Tablet, delayed releaseOral600 mg
SolutionIntravenous2 mg/mL
SolutionIntravenous200 mg
InjectionIntravenous600 mg/300mL
Injection, solutionIntravenous400 mg/200mL
SuspensionOral100 mg/5mL
Tablet, film coatedOral400 mg/1
Tablet, film coatedOral600 mg/1
Solution2 mg/1ml
Tablet, film coatedOral600 mg
GranuleOral
For solutionIntravenous
Granule, for suspensionOral20 mg/ml
InjectionIntravenous2 mg/ml
Powder, for suspensionOral100 mg / 5 mL
SolutionIntravenous2 mg / mL
Granule, for suspensionOral100 mg/5ml
Injection, solutionIntravenous2 mg/ml
Tablet, film coatedOral400 mg
Granule, for suspensionOral
Powder, for suspensionOral100 mg
TabletOral400 mg
GranuleOral100 MG/5ML
Tablet, coatedOral600 mg
Injection, solution2 mg/1ml
Prices
Unit descriptionCostUnit
Zyvox 600 mg tablet93.81USD tablet
Zyvox 200 mg/100 ml iv soln0.6USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5688792No1997-11-182014-11-18US flag
CA2168560No2001-08-142014-08-16Canada flag
US6559305Yes2003-05-062021-07-29US flag
US6514529Yes2003-02-042021-09-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)154.5https://pdf.hres.ca/dpd_pm/00045786.PDF
water solubility3 mg/mLhttps://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf
logP0.9Not Available
pKa1.8https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP0.61ALOGPS
logP0.64ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)14.45ChemAxon
pKa (Strongest Basic)-0.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.11 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.47 m3·mol-1ChemAxon
Polarizability34.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9363
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.5881
P-glycoprotein inhibitor IInhibitor0.7599
P-glycoprotein inhibitor IINon-inhibitor0.6478
Renal organic cation transporterNon-inhibitor0.7469
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5904
CYP450 1A2 substrateNon-inhibitor0.7811
CYP450 2C9 inhibitorNon-inhibitor0.8174
CYP450 2D6 inhibitorNon-inhibitor0.8112
CYP450 2C19 inhibitorNon-inhibitor0.5664
CYP450 3A4 inhibitorNon-inhibitor0.7563
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5544
Ames testNon AMES toxic0.6839
CarcinogenicityNon-carcinogens0.8916
BiodegradationNot ready biodegradable0.9895
Rat acute toxicity2.4938 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7883
hERG inhibition (predictor II)Inhibitor0.6297
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0009000000-05a0d0b23e80851df1d5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000j-0396000000-959c643931df034e05fc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000b-0940000000-066fc762e228726946fb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0292-0900000000-99847141a31b0134dcfa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000j-0900000000-7cf676c358a3890ab460
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000j-0900000000-fdccf108eb9fcb8a102d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-1649000000-a1dedd5c256e9f3bfa4f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0649000000-1ac199ac8af65a2644f8

Targets

Drugtargets2
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Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.
References
  1. Sinclair A, Arnold C, Woodford N: Rapid detection and estimation by pyrosequencing of 23S rRNA genes with a single nucleotide polymorphism conferring linezolid resistance in Enterococci. Antimicrob Agents Chemother. 2003 Nov;47(11):3620-2. [Article]
  2. Meka VG, Pillai SK, Sakoulas G, Wennersten C, Venkataraman L, DeGirolami PC, Eliopoulos GM, Moellering RC Jr, Gold HS: Linezolid resistance in sequential Staphylococcus aureus isolates associated with a T2500A mutation in the 23S rRNA gene and loss of a single copy of rRNA. J Infect Dis. 2004 Jul 15;190(2):311-7. Epub 2004 Jun 9. [Article]
  3. Zhu W, Tenover FC, Limor J, Lonsway D, Prince D, Dunne WM Jr, Patel JB: Use of pyrosequencing to identify point mutations in domain V of 23S rRNA genes of linezolid-resistant Staphylococcus aureus and Staphylococcus epidermidis. Eur J Clin Microbiol Infect Dis. 2007 Mar;26(3):161-5. [Article]
  4. Colca JR, McDonald WG, Waldon DJ, Thomasco LM, Gadwood RC, Lund ET, Cavey GS, Mathews WR, Adams LD, Cecil ET, Pearson JD, Bock JH, Mott JE, Shinabarger DL, Xiong L, Mankin AS: Cross-linking in the living cell locates the site of action of oxazolidinone antibiotics. J Biol Chem. 2003 Jun 13;278(24):21972-9. Epub 2003 Apr 10. [Article]
  5. FDA Approved Drug Products: Zyvox (linezolid) for intravenous or oral administration [Link]
  6. FDA Pharmacology and Biopharmaceutics Review: Linezolid [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Stevens DL, Dotter B, Madaras-Kelly K: A review of linezolid: the first oxazolidinone antibiotic. Expert Rev Anti Infect Ther. 2004 Feb;2(1):51-9. [Article]
  2. Taylor JJ, Wilson JW, Estes LL: Linezolid and serotonergic drug interactions: a retrospective survey. Clin Infect Dis. 2006 Jul 15;43(2):180-7. Epub 2006 Jun 9. [Article]
  3. FDA Approved Drug Products: Zyvox (linezolid) for intravenous or oral administration [Link]
  4. FDA Pharmacology and Biopharmaceutics Review: Linezolid [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Stevens DL, Dotter B, Madaras-Kelly K: A review of linezolid: the first oxazolidinone antibiotic. Expert Rev Anti Infect Ther. 2004 Feb;2(1):51-9. [Article]
  2. Taylor JJ, Wilson JW, Estes LL: Linezolid and serotonergic drug interactions: a retrospective survey. Clin Infect Dis. 2006 Jul 15;43(2):180-7. Epub 2006 Jun 9. [Article]
  3. FDA Approved Drug Products: Zyvox (linezolid) for intravenous or oral administration [Link]
  4. FDA Pharmacology and Biopharmaceutics Review: Linezolid [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Stalker DJ, Jungbluth GL: Clinical pharmacokinetics of linezolid, a novel oxazolidinone antibacterial. Clin Pharmacokinet. 2003;42(13):1129-40. doi: 10.2165/00003088-200342130-00004. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Parvez MM, Kaisar N, Shin HJ, Jung JA, Shin JG: Inhibitory Interaction Potential of 22 Antituberculosis Drugs on Organic Anion and Cation Transporters of the SLC22A Family. Antimicrob Agents Chemother. 2016 Oct 21;60(11):6558-6567. doi: 10.1128/AAC.01151-16. Print 2016 Nov. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Parvez MM, Kaisar N, Shin HJ, Jung JA, Shin JG: Inhibitory Interaction Potential of 22 Antituberculosis Drugs on Organic Anion and Cation Transporters of the SLC22A Family. Antimicrob Agents Chemother. 2016 Oct 21;60(11):6558-6567. doi: 10.1128/AAC.01151-16. Print 2016 Nov. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 20, 2021 19:48