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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
LinezolidTablet, film coated600 mg/1OralApotex Corp.2015-06-22Not applicableUs
LinezolidSuspension100 mg/5mLOralGreenstone LLC2015-05-18Not applicableUs
LinezolidTablet600 mgOralPanda Pharmaceuticals Inc.Not applicableNot applicableCanada
LinezolidInjection, solution2 mg/mLIntravenousHospira, Inc.2015-06-18Not applicableUs
Linezolid InjectionSolution2 mgIntravenousTeva Canada Limited2014-08-18Not applicableCanada
Linezolid InjectionSolution2 mgIntravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Linezolid InjectionSolution2 mgIntravenousFresenius Kabi Canada Ltd2015-06-12Not applicableCanada
Linezolid InjectionSolution2 mgIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Novo-linezolidTablet600 mgOralTeva Canada LimitedNot applicableNot applicableCanada
Sandoz LinezolidTablet600 mgOralSandoz Canada Incorporated2014-08-25Not applicableCanada
ZyvoxTablet, film coated600 mg/1OralPharmacia And Upjohn Company Llc2015-10-12Not applicableUs
ZyvoxInjection, solution600 mg/300mLIntravenousPharmacia and Upjohn Company2015-07-06Not applicableUs
ZyvoxTablet, film coated600 mg/1OralREMEDYREPACK INC.2012-11-272017-11-08Us
ZyvoxTablet, film coated600 mg/1OralPharmacia And Upjohn Company Llc2000-04-18Not applicableUs
ZyvoxTablet, film coated600 mg/1OralRebel Distributors Corp2000-04-18Not applicableUs
ZyvoxInjection, solution400 mg/200mLIntravenousPharmacia And Upjohn Company Llc2000-04-18Not applicableUs
ZyvoxInjection, solution600 mg/300mLIntravenousPharmacia and Upjohn Company2015-02-18Not applicableUs
ZyvoxSuspension100 mg/5mLOralDepartment Of State Health Services, Pharmacy Branch2000-04-18Not applicableUs
ZyvoxTablet, film coated600 mg/1OralCardinal Health2000-04-18Not applicableUs
ZyvoxSuspension100 mg/5mLOralPharmacia And Upjohn Company Llc2000-04-18Not applicableUs
ZyvoxInjection, solution600 mg/300mLIntravenousPharmacia And Upjohn Company Llc2000-04-18Not applicableUs
ZyvoxInjection, solution200 mg/100mLIntravenousPharmacia And Upjohn Company Llc2000-04-18Not 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
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/1OralTeva Pharmaceuticals Usa, Inc.2016-06-01Not applicableUs
LinezolidTablet, film coated600 mg/1OralMylan Institutional Inc.2016-01-22Not applicableUs
LinezolidInjection, solution600 mg/300mLIntravenousAuro Medics Pharma Llc2016-08-04Not 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
LinezolidInjection, solution200 mg/100mLIntravenousSandoz Inc2016-06-15Not applicableUs
LinezolidInjection, solution2 mg/mLIntravenousFresenius Kabi USA, LLC2015-06-22Not applicableUs
LinezolidTablet, film coated600 mg/1OralAlembic Pharmaceuticals Inc.2015-12-22Not applicableUs
LinezolidInjection, solution600 mg/300mLIntravenousSandoz Inc2016-06-15Not applicableUs
LinezolidInjection, solution2 mg/mLIntravenousTeva Parenteral Medicines, Inc.2015-01-05Not applicableUs
LinezolidPowder, for suspension100 mg/5mLOralWest Ward Pharmaceuticals Corp.2015-06-03Not applicableUs
LinezolidTablet600 mg/1OralAmneal Pharmaceuticals of New York, LLC2015-05-19Not applicableUs
LinezolidTablet, film coated600 mg/1OralAmerican Health Packaging2016-01-01Not applicableUs
LinezolidTablet600 mg/1OralNovel Laboratories, Inc.2016-08-22Not applicableUs
LinezolidTablet, film coated600 mg/1OralMajor Pharmaceuticals2015-12-21Not applicableUs
LinezolidTablet, film coated600 mg/1OralAv Pak2015-12-31Not 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 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[[email protected]]1CN(C(=O)O1)C1=CC(F)=C(C=C1)N1CCOCC1
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.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
23S rRNANucleotideyes
inhibitor
Enteric bacteria and other eubacterianot applicabledetails
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
Interactions
Drug Interactions
DrugInteractionDrug group
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.Experimental
AcebutololLinezolid may increase the hypertensive activities of Acebutolol.Approved
AcepromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Acepromazine.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Aceprometazine.Approved
AcetophenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Acetophenazine.Approved
AlmotriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Almotriptan.Approved, Investigational
AmineptineLinezolid may increase the serotonergic activities of Amineptine.Illicit, Withdrawn
AmisulprideThe risk or severity of adverse effects can be increased when Linezolid is combined with Amisulpride.Approved, Investigational
AmitriptylineLinezolid may increase the serotonergic activities of Amitriptyline.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Linezolid.Approved
AmperozideThe risk or severity of adverse effects can be increased when Linezolid is combined with Amperozide.Experimental
AmphetamineLinezolid may increase the hypertensive activities of Amphetamine.Approved, Illicit
AripiprazoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Aripiprazole.Approved, Investigational
AsenapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Asenapine.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Azaperone.Vet Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Linezolid.Investigational
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Linezolid.Withdrawn
BenperidolThe risk or severity of adverse effects can be increased when Linezolid is combined with Benperidol.Investigational
BenzphetamineLinezolid may increase the hypertensive activities of Benzphetamine.Approved, Illicit
BifeprunoxThe risk or severity of adverse effects can be increased when Linezolid is combined with Bifeprunox.Investigational
BrexpiprazoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Brexpiprazole.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Linezolid is combined with Bromocriptine.Approved, Investigational
BromperidolThe risk or severity of adverse effects can be increased when Linezolid is combined with Bromperidol.Investigational
BucindololLinezolid may increase the hypertensive activities of Bucindolol.Investigational
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Linezolid.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Linezolid.Approved
CariprazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Cariprazine.Approved
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Linezolid.Withdrawn
CeliprololLinezolid may increase the hypertensive activities of Celiprolol.Approved, Investigational
ChlorphentermineLinezolid may increase the hypertensive activities of Chlorphentermine.Illicit, Withdrawn
ChlorpromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Chlorpromazine.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Linezolid is combined with Chlorprothixene.Approved, Withdrawn
CitalopramLinezolid may increase the serotonergic activities of Citalopram.Approved
ClenbuterolLinezolid may increase the hypertensive activities of Clenbuterol.Approved, Vet Approved
ClomipramineLinezolid may increase the serotonergic activities of Clomipramine.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Clozapine.Approved
CyamemazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Cyamemazine.Approved
CyclobenzaprineLinezolid may increase the serotonergic activities of Cyclobenzaprine.Approved
DapiprazoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Dapiprazole.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Linezolid.Investigational
DesipramineLinezolid may increase the serotonergic activities of Desipramine.Approved
DesvenlafaxineLinezolid may increase the serotonergic activities of Desvenlafaxine.Approved
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Linezolid.Approved
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Linezolid.Approved
DobutamineLinezolid may increase the hypertensive activities of Dobutamine.Approved
DolasetronDolasetron may increase the serotonergic activities of Linezolid.Approved
DopamineLinezolid may increase the hypertensive activities of Dopamine.Approved
DosulepinLinezolid may increase the serotonergic activities of Dosulepin.Approved
DoxepinLinezolid may increase the serotonergic activities of Doxepin.Approved
DroperidolThe risk or severity of adverse effects can be increased when Linezolid is combined with Droperidol.Approved, Vet Approved
DuloxetineLinezolid may increase the serotonergic activities of Duloxetine.Approved
EcopipamThe risk or severity of adverse effects can be increased when Linezolid is combined with Ecopipam.Investigational
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Linezolid.Approved, Investigational
EphedrineLinezolid may increase the hypertensive activities of Ephedrine.Approved
EpinephrineLinezolid may increase the hypertensive activities of Epinephrine.Approved, Vet Approved
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Linezolid is combined with Ergoloid mesylate.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Linezolid is combined with Ergonovine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Linezolid is combined with Ergotamine.Approved
EscitalopramLinezolid may increase the serotonergic activities of Escitalopram.Approved, Investigational
EsmirtazapineLinezolid may increase the serotonergic activities of Esmirtazapine.Investigational
EtilefrineLinezolid may increase the hypertensive activities of Etilefrine.Withdrawn
EtoperidoneLinezolid may increase the serotonergic activities of Etoperidone.Approved
FencamfamineThe risk or severity of adverse effects can be increased when Linezolid is combined with Fencamfamine.Approved, Illicit, Withdrawn
FenoterolLinezolid may increase the hypertensive activities of Fenoterol.Approved
FentanylThe risk or severity of adverse effects can be increased when Linezolid is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FluoxetineLinezolid may increase the serotonergic activities of Fluoxetine.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Linezolid is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Fluphenazine.Approved
FluspirileneThe risk or severity of adverse effects can be increased when Linezolid is combined with Fluspirilene.Approved
FluvoxamineLinezolid may increase the serotonergic activities of Fluvoxamine.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Frovatriptan.Approved, Investigational
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Linezolid.Approved, Vet Approved
GranisetronGranisetron may increase the serotonergic activities of Linezolid.Approved, Investigational
HaloperidolThe risk or severity of adverse effects can be increased when Linezolid is combined with Haloperidol.Approved
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Linezolid.Approved
Hydroxyamphetamine hydrobromideLinezolid may increase the hypertensive activities of Hydroxyamphetamine hydrobromide.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Iloperidone.Approved
ImipramineLinezolid may increase the serotonergic activities of Imipramine.Approved
IndalpineLinezolid may increase the serotonergic activities of Indalpine.Investigational, Withdrawn
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Linezolid.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Linezolid.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Linezolid.Approved
IsoprenalineLinezolid may increase the hypertensive activities of Isoprenaline.Approved
IsoxsuprineLinezolid may increase the hypertensive activities of Isoxsuprine.Approved, Withdrawn
LabetalolLinezolid may increase the hypertensive activities of Labetalol.Approved
LevomilnacipranLinezolid may increase the serotonergic activities of Levomilnacipran.Approved
LithiumThe risk or severity of adverse effects can be increased when Linezolid is combined with Lithium.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Linezolid is combined with Lorcaserin.Approved
LoxapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Loxapine.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Lurasidone.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Linezolid is combined with Maprotiline.Approved
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Linezolid.Withdrawn
MelperoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Melperone.Approved
MephentermineLinezolid may increase the hypertensive activities of Mephentermine.Approved
MesoridazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Mesoridazine.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Linezolid.Withdrawn
MetaraminolLinezolid may increase the hypertensive activities of Metaraminol.Approved, Investigational
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Linezolid.Approved
MethamphetamineLinezolid may increase the hypertensive activities of Methamphetamine.Approved, Illicit
MethotrimeprazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Methotrimeprazine.Approved
MethoxamineLinezolid may increase the hypertensive activities of Methoxamine.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Linezolid.Investigational
MetoclopramideThe risk or severity of adverse effects can be increased when Linezolid is combined with Metoclopramide.Approved, Investigational
MidodrineLinezolid may increase the hypertensive activities of Midodrine.Approved
MilnacipranLinezolid may increase the serotonergic activities of Milnacipran.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Linezolid.Approved
MirtazapineLinezolid may increase the serotonergic activities of Mirtazapine.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Linezolid.Approved
MolindoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Molindone.Approved
NaratriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Naratriptan.Approved, Investigational
NefazodoneLinezolid may increase the serotonergic activities of Nefazodone.Approved, Withdrawn
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Linezolid.Withdrawn
NorepinephrineLinezolid may increase the hypertensive activities of Norepinephrine.Approved
NortriptylineLinezolid may increase the serotonergic activities of Nortriptyline.Approved
NylidrinLinezolid may increase the hypertensive activities of Nylidrin.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Linezolid.Withdrawn
OlanzapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Olanzapine.Approved, Investigational
OndansetronOndansetron may increase the serotonergic activities of Linezolid.Approved
OpipramolLinezolid may increase the serotonergic activities of Opipramol.Investigational
OrciprenalineLinezolid may increase the hypertensive activities of Orciprenaline.Approved
OsanetantThe risk or severity of adverse effects can be increased when Linezolid is combined with Osanetant.Investigational
OxymetazolineLinezolid may increase the hypertensive activities of Oxymetazoline.Approved
PaliperidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Paliperidone.Approved
PalonosetronPalonosetron may increase the serotonergic activities of Linezolid.Approved, Investigational
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Linezolid.Approved
ParoxetineLinezolid may increase the serotonergic activities of Paroxetine.Approved, Investigational
PerazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Linezolid is combined with Perospirone.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Perphenazine.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Linezolid.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Linezolid.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Linezolid.Withdrawn
PhenmetrazineLinezolid may increase the hypertensive activities of Phenmetrazine.Approved, Illicit
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Linezolid.Withdrawn
PhentermineLinezolid may increase the hypertensive activities of Phentermine.Approved, Illicit
PhenylephrineLinezolid may increase the hypertensive activities of Phenylephrine.Approved
PhenylpropanolamineLinezolid may increase the hypertensive activities of Phenylpropanolamine.Approved, Vet Approved, Withdrawn
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Linezolid.Approved
PimozideThe risk or severity of adverse effects can be increased when Linezolid is combined with Pimozide.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Pipamperone.Approved
PipotiazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Pipotiazine.Approved
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Linezolid.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Linezolid.Withdrawn
ProcarbazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Procarbazine.Approved
ProcaterolLinezolid may increase the hypertensive activities of Procaterol.Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Prochlorperazine.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Promazine.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Promethazine.Approved
PropericiazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Propericiazine.Approved
ProthipendylThe risk or severity of adverse effects can be increased when Linezolid is combined with Prothipendyl.Investigational
ProtriptylineLinezolid may increase the serotonergic activities of Protriptyline.Approved
PseudoephedrineLinezolid may increase the hypertensive activities of Pseudoephedrine.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Quetiapine.Approved
RacepinephrineLinezolid may increase the hypertensive activities of Racepinephrine.Approved
RacloprideThe risk or severity of adverse effects can be increased when Linezolid is combined with Raclopride.Investigational
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Linezolid.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Linezolid is combined with Remoxipride.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Linezolid is combined with Reserpine.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Risperidone.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Linezolid is combined with Ritanserin.Investigational
RitodrineLinezolid may increase the hypertensive activities of Ritodrine.Approved
RizatriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Rizatriptan.Approved
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Linezolid.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Linezolid.Approved, Investigational, Vet Approved
SertindoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Sertindole.Approved, Withdrawn
SertralineLinezolid may increase the serotonergic activities of Sertraline.Approved
SulpirideThe risk or severity of adverse effects can be increased when Linezolid is combined with Sulpiride.Approved
SumatriptanThe risk or severity of adverse effects can be increased when Linezolid is combined with Sumatriptan.Approved, Investigational
SynephrineLinezolid may increase the hypertensive activities of Synephrine.Experimental
TapentadolThe risk or severity of adverse effects can be increased when Linezolid is combined with Tapentadol.Approved
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Linezolid.Approved
TerbutalineLinezolid may increase the hypertensive activities of Terbutaline.Approved
TetryzolineLinezolid may increase the hypertensive activities of Tetryzoline.Approved
ThioproperazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Thioproperazine.Approved
ThioridazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Thioridazine.Approved
ThiothixeneThe risk or severity of adverse effects can be increased when Linezolid is combined with Thiothixene.Approved
TianeptineLinezolid may increase the serotonergic activities of Tianeptine.Approved
TiaprideThe risk or severity of adverse effects can be increased when Linezolid is combined with Tiapride.Investigational
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Linezolid.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Linezolid.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Linezolid.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Linezolid.Approved
TrazodoneLinezolid may increase the serotonergic activities of Trazodone.Approved, Investigational
TrifluoperazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Trifluoperazine.Approved
TriflupromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Triflupromazine.Approved, Vet Approved
TrimipramineLinezolid may increase the serotonergic activities of Trimipramine.Approved
TropisetronTropisetron may increase the serotonergic activities of Linezolid.Investigational
TyramineLinezolid may increase the hypertensive activities of Tyramine.Investigational, Nutraceutical
VenlafaxineLinezolid may increase the serotonergic activities of Venlafaxine.Approved
VilazodoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Vilazodone.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Linezolid is combined with Vortioxetine.Approved
ZimelidineLinezolid may increase the serotonergic activities of Zimelidine.Withdrawn
ZiprasidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Ziprasidone.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Linezolid.Approved, Investigational
ZotepineThe risk or severity of adverse effects can be increased when Linezolid is combined with Zotepine.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Linezolid is combined with Zuclopenthixol.Approved, Investigational
Food Interactions
  • Take without regard to meals.
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)
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
Powder, for suspensionOral100 mg/5mL
TabletOral600 mg/1
Tablet, film coatedOral600 mg/1
Injection, solutionIntravenous200 mg/100mL
Injection, solutionIntravenous400 mg/200mL
Injection, solutionIntravenous600 mg/300mL
SuspensionOral100 mg/5mL
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
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

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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 09, 2016 03:54