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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
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Linezolidtablet, film coated600 mg/1oralApotex Corp.2015-06-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidsuspension100 mg/5mLoralGreenstone LLC2015-05-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidinjection, solution2 mg/mLintravenousHospira, Inc.2015-06-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralTeva Pharmaceuticals USA Inc2015-06-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralGreenstone LLC2015-10-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolid Injectionsolution2 mgintravenousHospira Healthcare CorporationNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Linezolid Injectionsolution2 mgintravenousSandoz Canada IncorporatedNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Linezolid Injectionsolution2 mgintravenousFresenius Kabi Canada Ltd2015-06-12Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Linezolid Injectionsolution2 mgintravenousTeva Canada Limited2014-08-18Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-linezolidtablet600 mgoralTeva Canada LimitedNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Sandoz Linezolidtablet600 mgoralSandoz Canada Incorporated2014-08-25Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Zyvoxinjection, solution600 mg/300mLintravenousPharmacia and Upjohn Company2015-07-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxinjection, solution600 mg/300mLintravenousPharmacia and Upjohn Company2015-02-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxinjection, solution600 mg/300mLintravenousPharmacia and Upjohn Company2000-04-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxinjection, solution400 mg/200mLintravenousPharmacia and Upjohn Company2000-04-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mg/1oralCardinal Health2000-04-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mg/1oralPharmacia and Upjohn Company2015-10-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mg/1oralREMEDYREPACK INC.2013-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxinjection, solution200 mg/100mLintravenousPharmacia and Upjohn Company2000-04-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mg/1oralRebel Distributors Corp2000-04-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxsuspension100 mg/5mLoralPharmacia and Upjohn Company2000-04-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxtablet, film coated600 mg/1oralPharmacia and Upjohn Company2000-04-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyvoxampowder for suspension3 goralPfizer Canada Inc2010-08-04Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Zyvoxam 2 mg/mlsolution2 mgintravenousPfizer Canada Inc2001-06-07Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Zyvoxam 600 mgtablet600 mgoralPfizer Canada Inc2001-04-06Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-linezolidtablet600 mgoralApotex Inc2014-08-19Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Linezolidtablet600 mg/1oralAmneal Pharmaceuticals of New York, LLC2015-05-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralAlembic Pharmaceuticals Inc.2015-12-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralMylan Institutional Inc.2016-01-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralCamber Pharmaceuticals, Inc.2015-12-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralAmerican Health Packaging2016-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralMajor Pharmaceuticals2015-12-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidinjection, solution2 mg/mLintravenousTeva Parenteral Medicines, Inc.2015-01-05Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralAv Pak2015-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidinjection, solution2 mg/mLintravenousHospira, Inc.2015-07-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralGlenmark Pharmaceuticals Inc., Usa2011-12-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralMylan Pharmaceuticals Inc.2015-12-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolidtablet, film coated600 mg/1oralAscend Laboratories, LLC2015-12-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Linezolid for Oral Solutionpowder, for suspension100 mg/5mLoralRoxane Laboratories, Inc.2015-11-18Not applicableUs 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
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[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 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
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 References
  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 increase the hypertensive activities of Acebutolol.
AcepromazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Acepromazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Acetophenazine.
AminophyllineLinezolid may increase the hypertensive activities of Aminophylline.
AmisulprideThe risk or severity of adverse effects can be increased when Linezolid is combined with Amisulpride.
AmitriptylineLinezolid may increase the serotonergic activities of Amitriptyline.
AmoxapineLinezolid may increase the serotonergic activities of Amoxapine.
AmphetamineLinezolid may increase the hypertensive activities of Amphetamine.
ApraclonidineThe risk or severity of adverse effects can be increased when Linezolid is combined with Apraclonidine.
ArformoterolLinezolid may increase the hypertensive activities of Arformoterol.
AripiprazoleThe risk or severity of adverse effects can be increased when Linezolid is combined with Aripiprazole.
ArmodafinilLinezolid may increase the hypertensive activities of Armodafinil.
AtomoxetineLinezolid may increase the central neurotoxic activities of Atomoxetine.
AtropineLinezolid may increase the hypertensive activities of Atropine.
BenzphetamineLinezolid may increase the hypertensive activities of Benzphetamine.
BenzquinamideThe risk or severity of adverse effects can be increased when Linezolid is combined with Benzquinamide.
BetahistineThe serum concentration of Betahistine can be increased when it is combined with Linezolid.
BezafibrateThe risk or severity of adverse effects can be increased when Linezolid is combined with Bezafibrate.
BrimonidineThe risk or severity of adverse effects can be increased when Linezolid is combined with Brimonidine.
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Linezolid.
BupropionLinezolid may increase the hypertensive activities of Bupropion.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Linezolid.
CaffeineLinezolid may increase the hypertensive activities of Caffeine.
CarbamazepineThe risk or severity of adverse effects can be increased when Carbamazepine is combined with Linezolid.
CarphenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Carphenazine.
ChlormezanoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Chlormezanone.
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.
ClenbuterolLinezolid may increase the hypertensive activities of Clenbuterol.
ClomipramineLinezolid may increase the serotonergic activities of Clomipramine.
ClozapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Clozapine.
CocaineLinezolid may increase the hypertensive activities of Cocaine.
CyclobenzaprineCyclobenzaprine may increase the serotonergic activities of Linezolid.
CyproheptadineLinezolid may increase the anticholinergic activities of Cyproheptadine.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Linezolid.
DesipramineLinezolid may increase the serotonergic activities of Desipramine.
DesvenlafaxineLinezolid may increase the serotonergic activities of Desvenlafaxine.
DexmethylphenidateLinezolid may increase the hypertensive activities of Dexmethylphenidate.
DextroamphetamineLinezolid may increase the hypertensive activities of Dextroamphetamine.
DextromethorphanLinezolid may increase the serotonergic activities of Dextromethorphan.
DiethylpropionLinezolid may increase the hypertensive activities of Diethylpropion.
DipivefrinLinezolid may increase the hypertensive activities of Dipivefrin.
DobutamineLinezolid may increase the hypertensive activities of Dobutamine.
DomperidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Domperidone.
DopamineLinezolid may increase the hypertensive activities of Dopamine.
DoxapramLinezolid may increase the hypertensive activities of Doxapram.
DoxepinLinezolid may increase the serotonergic activities of Doxepin.
DroperidolThe risk or severity of adverse effects can be increased when Linezolid is combined with Droperidol.
DuloxetineLinezolid may increase the serotonergic activities of Duloxetine.
DyphyllineLinezolid may increase the hypertensive activities of Dyphylline.
EphedrineLinezolid may increase the hypertensive activities of Ephedrine.
EpinephrineLinezolid may increase the hypertensive activities of Epinephrine.
EscitalopramLinezolid may increase the serotonergic activities of Escitalopram.
EthanolThe risk or severity of adverse effects can be increased when Ethanol is combined with Linezolid.
FencamfamineThe risk or severity of adverse effects can be increased when Linezolid is combined with Fencamfamine.
FenoterolLinezolid may increase the hypertensive activities of Fenoterol.
FluoxetineLinezolid may increase the serotonergic activities of Fluoxetine.
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.
FormoterolLinezolid may increase the hypertensive activities of Formoterol.
GranisetronGranisetron may increase the serotonergic activities of Linezolid.
HaloperidolThe risk or severity of adverse effects can be increased when Linezolid is combined with Haloperidol.
HydrocodoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Hydrocodone.
HydromorphoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Hydromorphone.
ImipramineLinezolid may increase the serotonergic activities of Imipramine.
IndacaterolLinezolid may increase the hypertensive activities of Indacaterol.
Insulin RegularLinezolid may increase the hypoglycemic activities of Insulin Regular.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Linezolid.
IsomethepteneThe risk or severity of adverse effects can be increased when Linezolid is combined with Isometheptene.
IsoprenalineLinezolid may increase the hypertensive activities of Isoprenaline.
L-TryptophanThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Linezolid.
LabetalolLinezolid may increase the hypertensive activities of Labetalol.
LevodopaThe risk or severity of adverse effects can be increased when Levodopa is combined with Linezolid.
LevomilnacipranLinezolid may increase the serotonergic activities of Levomilnacipran.
LevonordefrinLinezolid may increase the hypertensive activities of Levonordefrin.
LisdexamfetamineLinezolid may increase the hypertensive activities of Lisdexamfetamine.
LithiumThe risk or severity of adverse effects can be increased when Linezolid is combined with Lithium.
LoxapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Loxapine.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Linezolid.
MephentermineLinezolid may increase the hypertensive activities of Mephentermine.
MequitazineLinezolid may increase the anticholinergic activities of Mequitazine.
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 Linezolid is combined with Methadone.
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.
MethyldopaThe risk or severity of adverse effects can be increased when Linezolid is combined with Methyldopa.
Methylene blueLinezolid may increase the serotonergic activities of Methylene blue.
MethylphenidateLinezolid may increase the hypertensive activities of Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Linezolid is combined with Metoclopramide.
MianserinLinezolid may increase the neurotoxic activities of Mianserin.
MidodrineLinezolid may increase the hypertensive activities of Midodrine.
MilnacipranLinezolid may increase the serotonergic activities of Milnacipran.
MirtazapineLinezolid may increase the serotonergic activities of Mirtazapine.
MoclobemideThe risk or severity of adverse effects can be increased when Linezolid is combined with Moclobemide.
ModafinilLinezolid may increase the hypertensive activities of Modafinil.
MolindoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Molindone.
MorphineThe risk or severity of adverse effects can be increased when Linezolid is combined with Morphine.
NaphazolineLinezolid may increase the hypertensive activities of Naphazoline.
NefazodoneLinezolid may increase the serotonergic activities of Nefazodone.
NorepinephrineLinezolid may increase the hypertensive activities of Norepinephrine.
NortriptylineLinezolid may increase the serotonergic activities of Nortriptyline.
OlanzapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Olanzapine.
OlodaterolLinezolid may increase the hypertensive activities of Olodaterol.
OndansetronThe risk or severity of adverse effects can be increased when Linezolid is combined with Ondansetron.
OrciprenalineLinezolid may increase the hypertensive activities of Orciprenaline.
OxycodoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Oxycodone.
OxymetazolineLinezolid may increase the hypertensive activities of Oxymetazoline.
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Linezolid.
PaliperidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Paliperidone.
ParoxetineLinezolid may increase the serotonergic activities of Paroxetine.
PerphenazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Perphenazine.
PethidineLinezolid may increase the serotonergic activities of Pethidine.
PhendimetrazineLinezolid may increase the hypertensive activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Linezolid.
PhenmetrazineLinezolid may increase the hypertensive activities of Phenmetrazine.
PhentermineLinezolid may increase the hypertensive activities of Phentermine.
PhenylephrineLinezolid may increase the hypertensive activities of Phenylephrine.
PhenylpropanolamineLinezolid may increase the hypertensive activities of Phenylpropanolamine.
PholcodinePholcodine may increase the serotonergic activities of Linezolid.
PimozideThe risk or severity of adverse effects can be increased when Linezolid is combined with Pimozide.
PiperacetazineThe risk or severity of adverse effects can be increased when Linezolid is combined with Piperacetazine.
PirbuterolLinezolid may increase the hypertensive activities of Pirbuterol.
PizotifenLinezolid may increase the anticholinergic activities of Pizotifen.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Linezolid.
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.
PropylhexedrineLinezolid may increase the hypertensive activities of Propylhexedrine.
ProtriptylineLinezolid may increase the serotonergic activities of Protriptyline.
PseudoephedrineLinezolid may increase the hypertensive activities of Pseudoephedrine.
QuetiapineThe risk or severity of adverse effects can be increased when Linezolid is combined with Quetiapine.
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.
SalbutamolLinezolid may increase the hypertensive activities of Salbutamol.
SalmeterolLinezolid may increase the hypertensive activities of Salmeterol.
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.
Sodium picosulfateThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Linezolid.
SufentanilSufentanil may increase the serotonergic activities of Linezolid.
SulpirideThe risk or severity of adverse effects can be increased when Linezolid is combined with Sulpiride.
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Linezolid.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Linezolid.
TerbutalineLinezolid may increase the hypertensive activities of Terbutaline.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Linezolid.
TetryzolineLinezolid may increase the hypertensive activities of Tetryzoline.
TheophyllineLinezolid may increase the hypertensive activities of Theophylline.
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.
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Linezolid.
TolcaponeThe risk or severity of adverse effects can be increased when Tolcapone is combined with Linezolid.
TramadolTramadol may increase the neuroexcitatory activities of 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.
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.
TriprolidineLinezolid may increase the hypertensive activities of Triprolidine.
VenlafaxineLinezolid may increase the serotonergic activities of Venlafaxine.
VilazodoneLinezolid may increase the serotonergic activities of Vilazodone.
VortioxetineLinezolid may increase the serotonergic activities of Vortioxetine.
ZiprasidoneThe risk or severity of adverse effects can be increased when Linezolid is combined with Ziprasidone.
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

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