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Identification
NameLinezolid
Accession NumberDB00601  (APRD01073, DB08769)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionLinezolid 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
Linezolid
Linezolid
Linezolide
Linezolidum
N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide
External Identifiers
  • INF 0026
  • PNU 100766
  • U 100
  • U 100766
  • U 766
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Linezolidtablet, film coated600 mg/1oralGreenstone LLC2015-10-12Not applicableUs
Linezolidtablet, film coated600 mg/1oralTeva Pharmaceuticals USA Inc2015-06-22Not applicableUs
Linezolidinjection, solution2 mg/mLintravenousHospira, Inc.2015-06-18Not applicableUs
Linezolidsuspension100 mg/5mLoralGreenstone LLC2015-05-18Not applicableUs
Linezolidtablet, film coated600 mg/1oralApotex Corp.2015-06-22Not applicableUs
Linezolid Injectionsolution2 mgintravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Linezolid Injectionsolution2 mgintravenousTeva Canada Limited2014-08-18Not applicableCanada
Linezolid Injectionsolution2 mgintravenousFresenius Kabi Canada Ltd2015-06-12Not applicableCanada
Linezolid Injectionsolution2 mgintravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Novo-linezolidtablet600 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Sandoz Linezolidtablet600 mgoralSandoz Canada Incorporated2014-08-25Not applicableCanada
Zyvoxinjection, solution600 mg/300mLintravenousPharmacia and Upjohn Company2015-02-18Not applicableUs
Zyvoxinjection, solution600 mg/300mLintravenousPharmacia and Upjohn Company2015-07-06Not applicableUs
Zyvoxtablet, film coated600 mg/1oralREMEDYREPACK INC.2013-04-03Not applicableUs
Zyvoxtablet, film coated600 mg/1oralPharmacia and Upjohn Company2015-10-12Not applicableUs
Zyvoxtablet, film coated600 mg/1oralPharmacia and Upjohn Company2000-04-18Not applicableUs
Zyvoxtablet, film coated600 mg/1oralCardinal Health2000-04-18Not applicableUs
Zyvoxinjection, solution400 mg/200mLintravenousPharmacia and Upjohn Company2000-04-18Not applicableUs
Zyvoxsuspension100 mg/5mLoralDepartment Of State Health Services, Pharmacy Branch2000-04-18Not applicableUs
Zyvoxsuspension100 mg/5mLoralPharmacia and Upjohn Company2000-04-18Not applicableUs
Zyvoxinjection, solution600 mg/300mLintravenousPharmacia and Upjohn Company2000-04-18Not applicableUs
Zyvoxtablet, film coated600 mg/1oralRebel Distributors Corp2000-04-18Not applicableUs
Zyvoxinjection, solution200 mg/100mLintravenousPharmacia and Upjohn Company2000-04-18Not applicableUs
Zyvoxampowder for suspension3 goralPfizer Canada Inc2010-08-04Not applicableCanada
Zyvoxam 2 mg/mlsolution2 mgintravenousPfizer Canada Inc2001-06-07Not applicableCanada
Zyvoxam 600 mgtablet600 mgoralPfizer Canada Inc2001-04-06Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-linezolidtablet600 mgoralApotex Inc2014-08-19Not applicableCanada
Linezolidtablet600 mg/1oralAmneal Pharmaceuticals of New York, LLC2015-05-19Not applicableUs
Linezolidtablet, film coated600 mg/1oralMajor Pharmaceuticals2015-12-21Not applicableUs
Linezolidtablet, film coated600 mg/1oralAscend Laboratories, LLC2015-12-21Not applicableUs
Linezolidtablet, film coated600 mg/1oralMylan Pharmaceuticals Inc.2015-12-21Not applicableUs
Linezolidtablet, film coated600 mg/1oralAmerican Health Packaging2016-01-01Not applicableUs
Linezolidtablet, film coated600 mg/1oralCamber Pharmaceuticals, Inc.2015-12-21Not applicableUs
Linezolidtablet, film coated600 mg/1oralGlenmark Pharmaceuticals Inc., Usa2011-12-31Not applicableUs
Linezolidinjection, solution2 mg/mLintravenousHospira, Inc.2015-07-07Not applicableUs
Linezolidtablet, film coated600 mg/1oralMylan Institutional Inc.2016-01-22Not applicableUs
Linezolidtablet, film coated600 mg/1oralAlembic Pharmaceuticals Inc.2015-12-22Not applicableUs
Linezolidtablet, film coated600 mg/1oralAv Pak2015-12-31Not applicableUs
Linezolidinjection, solution2 mg/mLintravenousTeva Parenteral Medicines, Inc.2015-01-05Not applicableUs
Linezolidinjection, solution2 mg/mLintravenousFresenius Kabi USA, LLC2015-06-22Not applicableUs
Linezolid for Oral Solutionpowder, for suspension100 mg/5mLoralRoxane Laboratories, Inc.2015-11-18Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AntizolidVerisfield
LinoseptOrion
LinozidOrion
LizbidAbbott
LizemoxMolekule
LizolidGlenmark
XolidCorona
ZenixHemofarm
ZizolidBiofarma
ZodlinFDC
ZolinidTeva
ZyvoxidPfizer
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIISQ9I6J12J
CAS number165800-03-3
WeightAverage: 337.3461
Monoisotopic: 337.143784348
Chemical FormulaC16H20FN3O4
InChI KeyInChIKey=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[[email protected]]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.
Related Articles
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 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 )
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous2 mg/mL
Tabletoral600 mg/1
Powder, for suspensionoral100 mg/5mL
Injection, solutionintravenous200 mg/100mL
Injection, solutionintravenous400 mg/200mL
Injection, solutionintravenous600 mg/300mL
Suspensionoral100 mg/5mL
Tablet, film coatedoral600 mg/1
Powder for suspensionoral3 g
Solutionintravenous2 mg
Tabletoral600 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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2168560 No2001-08-142014-08-16Canada
US5688792 No1994-11-182014-11-18Us
US6514529 Yes2001-09-152021-09-15Us
US6559305 Yes2001-07-292021-07-29Us
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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

DrugSyn.org

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. [PubMed:16857689 ]
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
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE is combined with Linezolid.
AcebutololLinezolid may increase the hypertensive activities of Acebutolol.
AcepromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Aceprometazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Acetophenazine.
AlmotriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Almotriptan.
AmineptineLinezolid may increase the serotonergic activities of Amineptine.
AmisulprideThe risk or severity of adverse effects can be increased when Linezolid is combined with Amisulpride.
AmitriptylineLinezolid may increase the serotonergic activities of Amitriptyline.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Linezolid.
AmoxapineLinezolid may increase the serotonergic activities of Amoxapine.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Linezolid.
AmperozideThe risk or severity of adverse effects can be increased when Linezolid is combined with Amperozide.
AmphetamineLinezolid may increase the hypertensive activities of Amphetamine.
AripiprazoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Aripiprazole.
AsenapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Asenapine.
AzaperoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Azaperone.
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Linezolid.
BenzphetamineLinezolid may increase the hypertensive activities of Benzphetamine.
BifeprunoxThe risk or severity of adverse effects can be increased when Linezolid is combined with Bifeprunox.
BrexpiprazoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Brexpiprazole.
BromocriptineThe risk or severity of adverse effects can be increased when Linezolid is combined with Bromocriptine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Linezolid.
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Linezolid.
CariprazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Cariprazine.
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Linezolid.
CeliprololLinezolid may increase the hypertensive activities of Celiprolol.
ChlorphentermineLinezolid may increase the hypertensive activities of Chlorphentermine.
ChlorpromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Chlorpromazine.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Linezolid is combined with Chlorprothixene.
CitalopramLinezolid may increase the serotonergic activities of Citalopram.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Linezolid.
ClenbuterolLinezolid may increase the hypertensive activities of Clenbuterol.
ClomipramineLinezolid may increase the serotonergic activities of Clomipramine.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Linezolid.
ClozapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Clozapine.
CyamemazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Cyamemazine.
CyclobenzaprineLinezolid may increase the serotonergic activities of Cyclobenzaprine.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Linezolid.
DapiprazoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Dapiprazole.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Linezolid.
DapoxetineLinezolid may increase the serotonergic activities of Dapoxetine.
DesipramineLinezolid may increase the serotonergic activities of Desipramine.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Linezolid.
DesvenlafaxineLinezolid may increase the serotonergic activities of Desvenlafaxine.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Linezolid.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Linezolid.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Linezolid.
DobutamineLinezolid may increase the hypertensive activities of Dobutamine.
DolasetronDolasetron may increase the serotonergic activities of Linezolid.
DopamineLinezolid may increase the hypertensive activities of Dopamine.
DosulepinLinezolid may increase the serotonergic activities of Dosulepin.
DoxepinLinezolid may increase the serotonergic activities of Doxepin.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Linezolid.
DroperidolThe risk or severity of adverse effects can be increased when Linezolid is combined with Droperidol.
DuloxetineLinezolid may increase the serotonergic activities of Duloxetine.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Linezolid.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Linezolid.
EphedrineLinezolid may increase the hypertensive activities of Ephedrine.
EpinephrineLinezolid may increase the hypertensive activities of Epinephrine.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Linezolid is combined with Ergoloid mesylate.
ErgonovineThe risk or severity of adverse effects can be increased when Linezolid is combined with Ergonovine.
ErgotamineThe risk or severity of adverse effects can be increased when Linezolid is combined with Ergotamine.
EscitalopramLinezolid may increase the serotonergic activities of Escitalopram.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Linezolid.
EsmirtazapineLinezolid may increase the serotonergic activities of Esmirtazapine.
EtilefrineLinezolid may increase the hypertensive activities of Etilefrine.
EtoperidoneLinezolid may increase the serotonergic activities of Etoperidone.
FencamfamineThe risk or severity of adverse effects can be increased when Linezolid is combined with Fencamfamine.
FenfluramineLinezolid may increase the serotonergic activities of Fenfluramine.
FenoterolLinezolid may increase the hypertensive activities of Fenoterol.
FentanylThe risk or severity of adverse effects can be increased when Linezolid is combined with Fentanyl.
FluoxetineLinezolid may increase the serotonergic activities of Fluoxetine.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Linezolid.
FlupentixolThe risk or severity of adverse effects can be increased when Linezolid is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Linezolid is combined with Fluspirilene.
FluvoxamineLinezolid may increase the serotonergic activities of Fluvoxamine.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Linezolid.
FrovatriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Frovatriptan.
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Linezolid.
GranisetronGranisetron may increase the serotonergic activities of Linezolid.
HaloperidolThe risk or severity of adverse effects can be increased when Linezolid is combined with Haloperidol.
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Linezolid.
Hydroxyamphetamine hydrobromideLinezolid may increase the hypertensive activities of Hydroxyamphetamine hydrobromide.
IloperidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Iloperidone.
ImipramineLinezolid may increase the serotonergic activities of Imipramine.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Linezolid.
IndalpineLinezolid may increase the serotonergic activities of Indalpine.
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Linezolid.
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Linezolid.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Linezolid.
IsoprenalineLinezolid may increase the hypertensive activities of Isoprenaline.
IsoxsuprineLinezolid may increase the hypertensive activities of Isoxsuprine.
LabetalolLinezolid may increase the hypertensive activities of Labetalol.
LevomilnacipranLinezolid may increase the serotonergic activities of Levomilnacipran.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Linezolid.
LithiumThe risk or severity of adverse effects can be increased when Linezolid is combined with Lithium.
LorcaserinThe risk or severity of adverse effects can be increased when Linezolid is combined with Lorcaserin.
LoxapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Loxapine.
Lu AA21004Linezolid may increase the serotonergic activities of Lu AA21004.
LurasidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Lurasidone.
MaprotilineThe risk or severity of adverse effects can be increased when Linezolid is combined with Maprotiline.
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Linezolid.
MelperoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Melperone.
MephentermineLinezolid may increase the hypertensive activities of Mephentermine.
MesoridazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Mesoridazine.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Linezolid.
MetaraminolLinezolid may increase the hypertensive activities of Metaraminol.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Linezolid.
MethamphetamineLinezolid may increase the hypertensive activities of Methamphetamine.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Methotrimeprazine.
MethoxamineLinezolid may increase the hypertensive activities of Methoxamine.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Linezolid.
MetoclopramideThe risk or severity of adverse effects can be increased when Linezolid is combined with Metoclopramide.
MidodrineLinezolid may increase the hypertensive activities of Midodrine.
MilnacipranLinezolid may increase the serotonergic activities of Milnacipran.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Linezolid.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Linezolid.
MirtazapineLinezolid may increase the serotonergic activities of Mirtazapine.
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Linezolid.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Linezolid.
MolindoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Molindone.
NaratriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Naratriptan.
NefazodoneLinezolid may increase the serotonergic activities of Nefazodone.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Linezolid.
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Linezolid.
NorepinephrineLinezolid may increase the hypertensive activities of Norepinephrine.
NortriptylineLinezolid may increase the serotonergic activities of Nortriptyline.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Linezolid.
NylidrinLinezolid may increase the hypertensive activities of Nylidrin.
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Linezolid.
OlanzapineLinezolid may increase the serotonergic activities of Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Linezolid is combined with Ondansetron.
OndansetronOndansetron may increase the serotonergic activities of Linezolid.
OrciprenalineLinezolid may increase the hypertensive activities of Orciprenaline.
OsanetantThe risk or severity of adverse effects can be increased when Linezolid is combined with Osanetant.
OxymetazolineLinezolid may increase the hypertensive activities of Oxymetazoline.
PaliperidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Paliperidone.
PalonosetronPalonosetron may increase the serotonergic activities of Linezolid.
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Linezolid.
ParoxetineLinezolid may increase the serotonergic activities of Paroxetine.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Linezolid.
PerospironeThe risk or severity of adverse effects can be increased when Linezolid is combined with Perospirone.
PerphenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Perphenazine.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Linezolid.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Linezolid.
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Linezolid.
PhenmetrazineLinezolid may increase the hypertensive activities of Phenmetrazine.
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Linezolid.
PhentermineLinezolid may increase the hypertensive activities of Phentermine.
PhenylephrineLinezolid may increase the hypertensive activities of Phenylephrine.
PhenylpropanolamineLinezolid may increase the hypertensive activities of Phenylpropanolamine.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Linezolid.
PimozideThe risk or severity of adverse effects can be increased when Linezolid is combined with Pimozide.
PipamperoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Pipamperone.
PipotiazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Pipotiazine.
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Linezolid.
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Linezolid.
ProcarbazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Procarbazine.
ProcaterolLinezolid may increase the hypertensive activities of Procaterol.
ProchlorperazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Prochlorperazine.
PromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Promazine.
PromethazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Promethazine.
PropericiazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Propericiazine.
ProtriptylineLinezolid may increase the serotonergic activities of Protriptyline.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Linezolid.
PseudoephedrineLinezolid may increase the hypertensive activities of Pseudoephedrine.
QuetiapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Quetiapine.
RacepinephrineLinezolid may increase the hypertensive activities of Racepinephrine.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Linezolid.
RemoxiprideThe risk or severity of adverse effects can be increased when Linezolid is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Linezolid is combined with Reserpine.
RisperidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Risperidone.
RitodrineLinezolid may increase the hypertensive activities of Ritodrine.
RizatriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Rizatriptan.
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Linezolid.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Linezolid.
SertindoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Sertindole.
SertralineLinezolid may increase the serotonergic activities of Sertraline.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Linezolid.
SulpirideThe risk or severity of adverse effects can be increased when Linezolid is combined with Sulpiride.
SumatriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Sumatriptan.
SynephrineLinezolid may increase the hypertensive activities of Synephrine.
TapentadolThe risk or severity of adverse effects can be increased when Linezolid is combined with Tapentadol.
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Linezolid.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Linezolid is combined with Tedizolid Phosphate.
TerbutalineLinezolid may increase the hypertensive activities of Terbutaline.
TetryzolineLinezolid may increase the hypertensive activities of Tetryzoline.
ThioproperazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Thioproperazine.
ThioridazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Thioridazine.
ThiothixeneThe risk or severity of adverse effects can be increased when Linezolid is combined with Thiothixene.
TianeptineLinezolid may increase the serotonergic activities of Tianeptine.
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Linezolid.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Linezolid.
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Linezolid.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Linezolid.
TrazodoneLinezolid may increase the serotonergic activities of Trazodone.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Linezolid.
TrifluoperazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Triflupromazine.
TrimipramineLinezolid may increase the serotonergic activities of Trimipramine.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Linezolid.
TyramineLinezolid may increase the hypertensive activities of Tyramine.
VenlafaxineLinezolid may increase the serotonergic activities of Venlafaxine.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Linezolid.
VilazodoneLinezolid may increase the serotonergic activities of Vilazodone.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Linezolid.
VortioxetineLinezolid may increase the serotonergic activities of Vortioxetine.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Linezolid.
ZimelidineLinezolid may increase the serotonergic activities of Zimelidine.
ZiprasidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Ziprasidone.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Linezolid.
ZotepineThe risk or severity of adverse effects can be increased when Linezolid is combined with Zotepine.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Linezolid is combined with Zuclopenthixol.
Food Interactions
  • Take without regard to meals.

Targets

1. 23S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
Actions
inhibitor
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:17139284 ]
  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:17016423 ]
  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:14576130 ]
  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:15216466 ]
  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:17393201 ]
  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:12690106 ]
  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. doi: 10.1101/gr.089342.108. Epub 2009 Apr 6. [PubMed:19351617 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
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. [PubMed:15482171 ]
  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:16779744 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
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. [PubMed:15482171 ]
  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:16779744 ]
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Drug created on June 13, 2005 07:24 / Updated on September 25, 2016 03:31