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Identification
NameLinezolid
Accession NumberDB00601  (APRD01073, DB08769)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Linezolid is a synthetic antibiotic, the first of the oxazolidinone class, used for the treatment of infections caused by multi-resistant bacteria including streptococcus and methicillin-resistant Staphylococcus aureus (MRSA). The drug works by inhibiting the initiation of bacterial protein synthesis.

Structure
Thumb
Synonyms
SynonymLanguageCode
LinezolidGermanINN
LinezolidSpanishINN
LinezolideFrenchINN
LinezolidumLatinINN
N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamideNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Zyvoxtablet, film coated600 mgoralPharmacia and Upjohn Company2000-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxsuspension100 mg/5mLoralPharmacia and Upjohn Company2000-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxinjection, solution200 mg/100mLintravenousPharmacia and Upjohn Company2000-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxinjection, solution400 mg/200mLintravenousPharmacia and Upjohn Company2000-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxinjection, solution600 mg/300mLintravenousPharmacia and Upjohn Company2000-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mgoralRebel Distributors Corp2000-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mgoralREMEDYREPACK INC.2013-04-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mgoralREMEDYREPACK INC.2013-04-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mgoralCardinal Health2000-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxampowder for suspension3 goralPfizer Canada IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Linezolidinjection, solution2 mg/mLintravenousTeva Parenteral Medicines, Inc.2015-01-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet600 mgoralGlenmark Generics Inc., USA2011-12-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
AntizolidVerisfield
LinoseptOrion
LinozidOrion
LizbidAbbott
LizemoxMolekule
LizolidGlenmark
XolidCorona
ZenixHemofarm
ZizolidBiofarma
ZodlinFDC
ZolinidTeva
ZyvoxidPfizer
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number165800-03-3
WeightAverage: 337.3461
Monoisotopic: 337.143784348
Chemical FormulaC16H20FN3O4
InChI KeyTYZROVQLWOKYKF-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentPhenylmorpholines
Alternative Parents
Substituents
  • Phenylmorpholine
  • Substituted aniline
  • Dialkylarylamine
  • Halobenzene
  • Fluorobenzene
  • Aniline
  • Benzenoid
  • Oxazolidinone
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Acetamide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of bacterial infections caused by susceptible strains of vancomycin resistant Enterococcus faecium, Staphylococcal aureus (methicillin resistant and susceptible strains), Streptococcus pneumoniae, Streptococcus pyogenes, Streptococcus agalactiae.
PharmacodynamicsLinezolid is a synthetic antibacterial agent of a new class of antibiotics, the oxazolidinones, which has clinical utility in the treatment of infections caused by aerobic Gram-positive bacteria. The in vitro spectrum of activity of linezolid also includes certain Gram-negative bacteria and anaerobic bacteria. Susceptible organisms include methicillin- and vancomycin-resistant staphylococci, vancomycin-resistant enterococci, penicillin-resistant pneumococci and anaerobes. Oxazolidinones inhibit protein synthesis by binding at the P site at the ribosomal 50S subunit. Resistance to other protein synthesis inhibitors does not affect oxazolidinone activity, however rare development of oxazolidinone resistance cases, associated with 23S rRNA alterations during treatment have been reported. Linezolid inhibits bacterial protein synthesis through a mechanism of action different from that of other antibacterial agents; therefore, cross-resistance between linezolid and other classes of antibiotics is unlikely.
Mechanism of actionLinezolid is a synthetic antibacterial agent of the oxazolidinone class of antibiotics. It has in vitro activity against aerobic Gram positive bacteria, certain Gram negative bacteria and anaerobic microorganisms. It selectively inhibits bacterial protein synthesis through binding to sites on the bacterial ribosome and prevents the formation of a functional 70S-initiation complex. Specifically, linezolid 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 an essential component of the bacterial translation process. The results of time-kill studies have shown linezolid to be bacteriostatic against enterococci and staphylococci. For streptococci, linezolid was found to be bactericidal for the majority of strains. Linezolid is also a reversible, nonselective inhibitor of monoamine oxidase. Therefore, linezolid has the potential for interaction with adrenergic and serotonergic agents.
AbsorptionLinezolid is rapidly and extensively absorbed after oral dosing. Maximum plasma concentrations are reached approximately 1 to 2 hours after dosing, and the absolute bioavailability is approximately 100%.
Volume of distribution
  • 40 to 50 L [healthy adult volunteers]
Protein binding31%
Metabolism

Linezolid is primarily metabolized by oxidation of the morpholine ring, which results in two inactive ring-opened carboxylic acid metabolites: the aminoethoxyacetic acid metabolite (A), and the hydroxyethyl glycine metabolite

SubstrateEnzymesProduct
Linezolid
Not Available
aminoethoxyacetic acidDetails
Linezolid
Not Available
Hydroxyethyl glycineDetails
Route of eliminationNot Available
Half life4.5-5.5 hours
ClearanceNot Available
ToxicityClinical signs of acute toxicity lead to decreased activity, ataxia, vomiting and tremors.
Affected organisms
  • Gram negative and gram positive bacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8174
CYP450 2D6 substrateNon-inhibitor0.8112
CYP450 2C19 substrateNon-inhibitor0.5664
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous2 mg/mL
Injection, solutionintravenous200 mg/100mL
Injection, solutionintravenous400 mg/200mL
Injection, solutionintravenous600 mg/300mL
Powder for suspensionoral3 g
Suspensionoral100 mg/5mL
Tabletoral600 mg
Tablet, film coatedoral600 mg
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
CountryPatent NumberApprovedExpires (estimated)
Canada21685602001-08-142014-08-16
United States56887921994-11-182014-11-18
United States65145292001-09-152021-09-15
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility3 mg/mLNot Available
logP0.9Not Available
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US5688792
General Reference
  1. Link
  2. 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. Pubmed
External Links
ATC CodesJ01XX08
AHFS Codes
  • 08:12.28.24
PDB EntriesNot Available
FDA labelDownload (106 KB)
MSDSDownload (43.7 KB)
Interactions
Drug Interactions
Drug
AcebutololLinezolid may enhance the hypertensive effect of Sympathomimetics.
AcepromazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
AcetophenazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
AminophyllineMay enhance the hypertensive effect of Sympathomimetics.
AmisulprideSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
AmitriptylineMay enhance the serotonergic effect of Tricyclic Antidepressants. This could result in serotonin syndrome.
AmoxapineMay enhance the serotonergic effect of Tricyclic Antidepressants. This could result in serotonin syndrome.
AmphetamineMay enhance the hypertensive effect of Sympathomimetics.
ApraclonidineMAO Inhibitors may enhance the adverse/toxic effect of Apraclonidine. MAO Inhibitors may increase the serum concentration of Apraclonidine.
ArformoterolMay enhance the hypertensive effect of Sympathomimetics.
AripiprazoleSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
armodafinilMay enhance the hypertensive effect of Sympathomimetics.
ArticaineMay enhance the hypertensive effect of Sympathomimetics.
AtomoxetineMAO Inhibitors may enhance the neurotoxic (central) effect of AtoMOXetine.
BenzphetamineLinezolid may enhance the hypertensive effect of Sympathomimetics.
BenzquinamideSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
BetahistineMAO Inhibitors may increase the serum concentration of Betahistine.
BezafibrateMAO Inhibitors may enhance the adverse/toxic effect of Bezafibrate.
BuprenorphineMay enhance the adverse/toxic effect of MAO Inhibitors.
BupropionMAO Inhibitors may enhance the hypertensive effect of BuPROPion.
BuspironeMay enhance the adverse/toxic effect of MAO Inhibitors. Specifically, blood pressure elevations been reported.
CaffeineMay enhance the hypertensive effect of Sympathomimetics.
CarbamazepineMay enhance the adverse/toxic effect of MAO Inhibitors.
CarphenazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ChlormezanoneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ChlorphentermineLinezolid may enhance the hypertensive effect of Sympathomimetics.
ChlorpromazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ChlorprothixeneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
CitalopramMay enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This could result in serotonin syndrome.
ClenbuterolLinezolid may enhance the hypertensive effect of Sympathomimetics.
ClomipramineMay enhance the serotonergic effect of Tricyclic Antidepressants. This could result in serotonin syndrome.
ClozapineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
CocaineMay enhance the hypertensive effect of Sympathomimetics.
CyclobenzaprineMay enhance the serotonergic effect of MAO Inhibitors. This could result in serotonin syndrome.
CyproheptadineMAO Inhibitors may enhance the anticholinergic effect of Cyproheptadine. Cyproheptadine may diminish the serotonergic effect of MAO Inhibitors.
DapoxetineMay enhance the adverse/toxic effect of Serotonin Modulators.
DesipramineMay enhance the serotonergic effect of Tricyclic Antidepressants. This could result in serotonin syndrome.
DesvenlafaxineMay enhance the serotonergic effect of Serotonin/Norepinephrine Reuptake Inhibitors. This could result in serotonin syndrome.
DexmethylphenidateMAO Inhibitors may enhance the hypertensive effect of Dexmethylphenidate.
DextroamphetamineMay enhance the hypertensive effect of Sympathomimetics.
DextromethorphanMAO Inhibitors may enhance the serotonergic effect of Dextromethorphan. This may cause serotonin syndrome.
DiethylpropionMAO Inhibitors may enhance the hypertensive effect of Diethylpropion.
DihydrocodeineMay enhance the hypertensive effect of Sympathomimetics.
DipivefrinMay enhance the hypertensive effect of Sympathomimetics.
DobutamineLinezolid may enhance the hypertensive effect of Sympathomimetics.
DomperidoneMAO Inhibitors may enhance the adverse/toxic effect of Domperidone. MAO Inhibitors may diminish the therapeutic effect of Domperidone. Domperidone may diminish the therapeutic effect of MAO Inhibitors.
DopamineLinezolid may enhance the hypertensive effect of Sympathomimetics.
DoxapramMay enhance the hypertensive effect of Sympathomimetics.
DoxylamineMAO Inhibitors may enhance the anticholinergic effect of Doxylamine.
DroperidolSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
DuloxetineMay enhance the serotonergic effect of Serotonin/Norepinephrine Reuptake Inhibitors. This could result in serotonin syndrome.
EpinephrineLinezolid may enhance the hypertensive effect of Sympathomimetics.
EscitalopramMay enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This could result in serotonin syndrome.
FencamfamineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
FenoterolLinezolid may enhance the hypertensive effect of Sympathomimetics.
FluoxetineMay enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This could result in serotonin syndrome.
FlupentixolSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
FluphenazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
FluspirileneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
Fluticasone furoateMay enhance the hypertensive effect of Sympathomimetics.
FluvoxamineMay enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This could result in serotonin syndrome.
FormoterolLinezolid may enhance the hypertensive effect of Sympathomimetics.
HaloperidolSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
HydrocodoneMAO Inhibitors may enhance the adverse/toxic effect of Hydrocodone.
HydromorphoneMAO Inhibitors may enhance the adverse/toxic effect of HYDROmorphone.
ImipramineMay enhance the serotonergic effect of Tricyclic Antidepressants. This could result in serotonin syndrome.
IndacaterolMay enhance the hypertensive effect of Sympathomimetics.
Ipratropium bromideMay enhance the hypertensive effect of Sympathomimetics.
IsocarboxazidMAO Inhibitors may enhance the adverse/toxic effect of Linezolid.
IsomethepteneMAO Inhibitors may enhance the adverse/toxic effect of Isometheptene.
IsoprenalineLinezolid may enhance the hypertensive effect of Sympathomimetics.
LabetalolLinezolid may enhance the hypertensive effect of Sympathomimetics.
LevomilnacipranMay enhance the serotonergic effect of Serotonin/Norepinephrine Reuptake Inhibitors. This could result in serotonin syndrome.
LevonordefrinMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
LisdexamfetamineMay enhance the hypertensive effect of Sympathomimetics.
LithiumMAO Inhibitors may enhance the adverse/toxic effect of Lithium.
LoxapineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
MaprotilineMay enhance the adverse/toxic effect of MAO Inhibitors.
MephentermineLinezolid may enhance the hypertensive effect of Sympathomimetics.
MequitazineMAO Inhibitors may enhance the anticholinergic effect of Mequitazine.
MesoridazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
MetaraminolLinezolid may enhance the hypertensive effect of Sympathomimetics.
MethadoneMAO Inhibitors may enhance the adverse/toxic effect of Methadone.
MethamphetamineLinezolid may enhance the hypertensive effect of Sympathomimetics.
MethotrimeprazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
MethoxamineLinezolid may enhance the hypertensive effect of Sympathomimetics.
MethyldopaMAO Inhibitors may enhance the adverse/toxic effect of Methyldopa.
MethylphenidateMAO Inhibitors may enhance the hypertensive effect of Methylphenidate.
MetoclopramideSerotonin Modulators may enhance the adverse/toxic effect of Metoclopramide. This may be manifest as symptoms consistent with serotonin syndrome or neuroleptic malignant syndrome.
MianserinMAO Inhibitors may enhance the neurotoxic effect of Mianserin.
MidodrineMay enhance the hypertensive effect of Sympathomimetics.
MilnacipranMay enhance the serotonergic effect of Serotonin/Norepinephrine Reuptake Inhibitors. This could result in serotonin syndrome.
MirtazapineMay enhance the serotonergic effect of Mirtazapine. This could result in serotonin syndrome.
MoclobemideMAO Inhibitors may enhance the adverse/toxic effect of Linezolid.
ModafinilMay enhance the hypertensive effect of Sympathomimetics.
MolindoneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
NaphazolineLinezolid may enhance the hypertensive effect of Sympathomimetics.
NefazodoneLinezolid may enhance the serotonergic effect of Nefazodone. This could result in serotonin syndrome.
NorepinephrineMay enhance the hypertensive effect of Sympathomimetics.
NortriptylineMay enhance the serotonergic effect of Tricyclic Antidepressants. This could result in serotonin syndrome.
OlanzapineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
OndansetronSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
OrciprenalineLinezolid may enhance the hypertensive effect of Sympathomimetics.
OxycodoneMAO Inhibitors may enhance the adverse/toxic effect of OxyCODONE.
OxymetazolineLinezolid may enhance the hypertensive effect of Sympathomimetics.
OxymorphoneMay enhance the adverse/toxic effect of MAO Inhibitors.
PaliperidoneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ParoxetineMay enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This could result in serotonin syndrome.
PerphenazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
PhendimetrazineMay enhance the hypertensive effect of Sympathomimetics.
PhenelzineMAO Inhibitors may enhance the adverse/toxic effect of Linezolid.
PheniramineMay enhance the hypertensive effect of Sympathomimetics.
PhenmetrazineLinezolid may enhance the hypertensive effect of Sympathomimetics.
PhentermineMay enhance the hypertensive effect of Sympathomimetics.
PhenylephrineMay enhance the hypertensive effect of Sympathomimetics.
PhenylpropanolamineLinezolid may enhance the hypertensive effect of Sympathomimetics.
PimozideSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
PiperacetazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
PirbuterolMay enhance the hypertensive effect of Sympathomimetics.
PizotifenMAO Inhibitors may enhance the anticholinergic effect of Pizotifen.
ProcarbazineMAO Inhibitors may enhance the adverse/toxic effect of Linezolid.
ProchlorperazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
PromazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
PropylhexedrineMay enhance the hypertensive effect of Sympathomimetics.
ProtriptylineMay enhance the serotonergic effect of Tricyclic Antidepressants. This could result in serotonin syndrome.
PseudoephedrineMay enhance the hypertensive effect of Sympathomimetics.
QuetiapineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
RasagilineMAO Inhibitors may enhance the adverse/toxic effect of Linezolid.
RemoxiprideSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ReserpineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
RisperidoneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
RitodrineLinezolid may enhance the hypertensive effect of Sympathomimetics.
SalbutamolMay enhance the hypertensive effect of Sympathomimetics.
SalmeterolLinezolid may enhance the hypertensive effect of Sympathomimetics.
SelegilineMAO Inhibitors may enhance the adverse/toxic effect of Linezolid.
SertindoleSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
SertralineMay enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This could result in serotonin syndrome.
SulpirideSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
TapentadolMay enhance the adverse/toxic effect of MAO Inhibitors.
Tedizolid PhosphateMAO Inhibitors may enhance the adverse/toxic effect of Linezolid.
TerbutalineLinezolid may enhance the hypertensive effect of Sympathomimetics.
TetrabenazineMay enhance the adverse/toxic effect of MAO Inhibitors.
TheophyllineMay enhance the hypertensive effect of Sympathomimetics.
ThioridazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ThiothixeneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
TramadolMay enhance the neuroexcitatory and/or seizure-potentiating effect of MAO Inhibitors. TraMADol may enhance the serotonergic effect of MAO Inhibitors.
TranylcypromineMAO Inhibitors may enhance the adverse/toxic effect of Linezolid.
TrazodoneLinezolid may enhance the serotonergic effect of TraZODone. This could result in serotonin syndrome.
TrifluoperazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
TriflupromazineSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
TrimipramineMay enhance the serotonergic effect of Tricyclic Antidepressants. This could result in serotonin syndrome.
TriprolidineMay enhance the hypertensive effect of Sympathomimetics.
VenlafaxineMay enhance the serotonergic effect of Serotonin/Norepinephrine Reuptake Inhibitors. This could result in serotonin syndrome.
VilazodoneMay enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This could result in serotonin syndrome.
ZiprasidoneSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
ZuclopenthixolSerotonin Modulators may enhance the adverse/toxic effect of Antipsychotic Agents. Specifically, serotonin modulators may enhance dopamine blockade, possibly increasing the risk for neuroleptic malignant syndrome. Antipsychotic Agents may enhance the serotonergic effect of Serotonin Modulators. This could result in serotonin syndrome.
Food Interactions
  • Take without regard to meals.

Targets

1. 23S rRNA

Kind: nucleotide

Organism: Enteric bacteria and other eubacteria

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. 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. Pubmed
  7. Feng J, Lupien A, Gingras H, Wasserscheid J, Dewar K, Legare D, Ouellette M: Genome sequencing of linezolid-resistant Streptococcus pneumoniae mutants reveals novel mechanisms of resistance. Genome Res. 2009 Jul;19(7):1214-23. Epub 2009 Apr 6. Pubmed

Enzymes

1. Amine oxidase [flavin-containing] A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

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. Pubmed
  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. Pubmed

2. Amine oxidase [flavin-containing] B

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details

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. Pubmed
  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. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:24