Identification

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Name
Linezolid
Accession Number
DB00601  (APRD01073, DB08769)
Type
Small Molecule
Groups
Approved, 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
  • Linezolide
  • Linezolidum
  • N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide
External IDs
INF 0026 / PNU 100766 / U 100 / U 100766 / U 766 / U-100,766 / U-100766
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LinezolidInjection, solution2 mg/1mLIntravenousHospira, Inc.2015-06-18Not applicableUs
LinezolidTablet600 mgOralPanda Pharmaceuticals Inc.Not applicableNot applicableCanada
Linezolid InjectionSolutionIntravenousMda Inc.Not applicableNot applicableCanada
Linezolid InjectionSolutionIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Linezolid InjectionSolutionIntravenousFresenius Kabi2015-06-12Not applicableCanada
Linezolid InjectionSolutionIntravenousAuro Pharma IncNot applicableNot applicableCanada
Linezolid InjectionSolutionIntravenousTEVA Canada Limited2014-08-182018-05-17Canada
Linezolid InjectionSolutionIntravenousJamp Pharma CorporationNot applicableNot applicableCanada
Linezolid InjectionSolutionIntravenousNeo Health Canada Inc.Not applicableNot applicableCanada
Linezolid InjectionSolutionIntravenousHospira Healthcare UlcNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-linezolidTabletOralApotex Corporation2014-08-19Not applicableCanada
Gpc-linezolidTabletOralGeneric Partners (Canada) Inc.Not applicableNot applicableCanada
LinezolidTablet, film coated600 mg/1OralMylan Institutional Inc.2015-12-162019-05-31Us
LinezolidTablet, film coated600 mg/1OralZydus Pharmaceuticals Usa, Inc.2017-08-09Not applicableUs
LinezolidSuspension100 mg/5mLOralGreenstone, Llc2015-05-18Not applicableUs
LinezolidTablet, film coated600 mg/1OralTeva Pharmaceuticals USA, Inc.2016-06-032020-05-31Us00093 7490 34 nlmimage10 284f1448
LinezolidInjection, solution2 mg/1mLIntravenousFresenius Kabi2015-06-22Not applicableUs
LinezolidInjection, solution200 mg/100mLIntravenousSun Pharmaceutical Industries, Inc.2017-02-01Not applicableUs
LinezolidTablet, film coated600 mg/1OralMylan Pharmaceuticals Inc.2015-12-212019-05-31Us
LinezolidInjection, solution2 mg/1mLIntravenousTeva Parenteral Medicines, Inc.2015-01-05Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Antizolid (Verisfield) / Linosept (Orion) / Linozid (Orion) / Lizbid (Abbott) / Lizemox (Molekule) / Lizolid (Glenmark) / Xolid (Corona) / Zenix (Hemofarm) / Zizolid (Biofarma) / Zodlin (FDC) / Zolinid (Teva) / Zyvoxid (Pfizer)
Categories
UNII
ISQ9I6J12J
CAS number
165800-03-3
Weight
Average: 337.3461
Monoisotopic: 337.143784348
Chemical Formula
C16H20FN3O4
InChI Key
TYZROVQLWOKYKF-ZDUSSCGKSA-N
InChI
InChI=1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
IUPAC Name
N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
SMILES
CC(=O)NC[C@H]1CN(C(=O)O1)C1=CC(F)=C(C=C1)N1CCOCC1

Pharmacology

Indication

For 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.

Associated Conditions
Pharmacodynamics

Linezolid 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 action

Linezolid 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.

TargetActionsOrganism
A23S ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Linezolid 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 binding

31%

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

Route of elimination
Not Available
Half life

4.5-5.5 hours

Clearance
Not Available
Toxicity

Clinical signs of acute toxicity lead to decreased activity, ataxia, vomiting and tremors.

Affected organisms
  • Gram negative and gram positive bacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Linezolid is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Linezolid is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Linezolid is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Linezolid is combined with 1-benzylimidazole.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Linezolid is combined with 2-Methoxyethanol.
2,4-thiazolidinedioneLinezolid may increase the hypoglycemic activities of 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when Linezolid is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Linezolid is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when Linezolid is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Linezolid is combined with 4-hydroxycoumarin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take without regard to meals.

References

Synthesis Reference
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
Human Metabolome Database
HMDB0014739
KEGG Drug
D00947
KEGG Compound
C08146
PubChem Compound
441401
PubChem Substance
46504452
ChemSpider
390139
BindingDB
50116067
ChEBI
63607
ChEMBL
CHEMBL126
Therapeutic Targets Database
DAP000398
PharmGKB
PA450233
HET
ZLD
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Linezolid
ATC Codes
J01XX08 — Linezolid
AHFS Codes
  • 08:12.28.24 — Oxazolidinones
PDB Entries
3cpw / 3dll / 4k7q / 4wfa / 5nz0
FDA label
Download (106 KB)
MSDS
Download (43.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1Active Not RecruitingBasic ScienceHealthy Volunteers2
1Active Not RecruitingDiagnosticHealthy Volunteers1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableTuberculosis Infection1
1CompletedBasic ScienceBacterial Infections1
1CompletedBasic ScienceGram Positive Infection1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHuman Memory / Intranasal Insulin1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
1CompletedTreatmentMinor burns1
1WithdrawnPreventionNeurosurgery1
1WithdrawnTreatmentBacterial Infections1
1, 2CompletedTreatmentExtensively Drug Resistant Tuberculosis / Multi-Drug Resistant Tuberculosis2
1, 2CompletedTreatmentMulti-Drug Resistant Tuberculosis / Tuberculosis Infection1
2CompletedOtherCystic Fibrosis (CF)1
2CompletedTreatmentAbscesses / Bacterial Skin Diseases / Infectious Skin Diseases / Staphylococcal Skin Infections / Streptococcal Infections1
2CompletedTreatmentAlzheimer's Disease (AD) / Mild Cognitive Impairment (MCI)1
2CompletedTreatmentBacterial Infections3
2CompletedTreatmentBacterial Skin Disease / Infectious Skin Disease1
2CompletedTreatmentExtensively Drug Resistant Tuberculosis / Pulmonary Tuberculosis (TB) / Tuberculosis, Multidrug Resistant1
2CompletedTreatmentPulmonary Tuberculosis (TB)1
2CompletedTreatmentSkin Diseases, Bacterial1
2CompletedTreatmentSkin Infections, Bacterial1
2CompletedTreatmentSkin and Subcutaneous Tissue Bacterial Infections2
2CompletedTreatmentType 2 Diabetes Mellitus1
2CompletedTreatmentAcute acute bacterial skin and skin structure infections1
2Not Yet RecruitingTreatmentLinezolid / Tuberculous Meningitis1
2Not Yet RecruitingTreatmentTuberculous Meningitis1
2RecruitingTreatmentCognitive Impairments / Mild Cognitive Impairment (MCI)1
2RecruitingTreatmentHIV-1-infection / Tuberculosis Meningitis1
2RecruitingTreatmentInfections, Gram-Positive Bacterial / Skin Diseases, Bacterial1
2RecruitingTreatmentPulmonary Tuberculosis (TB)1
2RecruitingTreatmentTuberculosis, Multidrug Resistant1
2TerminatedTreatmentInfected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee1
2TerminatedTreatmentNeoplasms / Neutropenia, Febrile1
2TerminatedTreatmentOsteomyelitis1
2TerminatedTreatmentPneumonia, Bacterial1
2TerminatedTreatmentSafety and Tolerability1
2Unknown StatusTreatmentHip Prosthetic Joint Infection1
2Unknown StatusTreatmentPulmonary Tuberculosis Without Resistance to Rifampicin1
2WithdrawnOtherDiabetes Mellitus (DM)1
2, 3Active Not RecruitingTreatmentExtensively Drug Resistant Tuberculosis / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
2, 3CompletedTreatmentAlzheimer's Disease (AD) / Amnestic Mild Cognitive Impairment1
2, 3CompletedTreatmentInfections, Pediatrics1
2, 3Not Yet RecruitingTreatmentExtensively Drug Resistant Tuberculosis / Multi-Drug Resistant Tuberculosis / Pulmonary Tuberculosis (TB)1
2, 3Not Yet RecruitingTreatmentTuberculosis, Multidrug Resistant1
2, 3RecruitingTreatmentExtensively Drug Resistant Tuberculosis / Pulmonary Tuberculosis (TB) / Tuberculosis, Multidrug Resistant1
2, 3RecruitingTreatmentPulmonary Tuberculosis (TB)1
3Active Not RecruitingTreatmentPulmonary Tuberculosis (TB)1
3CompletedTreatmentAbscesses / Cellulitis / Surgical Site Infections / Wound Infections2
3CompletedTreatmentBacteremia / Bacterial Infections / Infections, Gram-Positive Bacterial1
3CompletedTreatmentBacterial Infections2
3CompletedTreatmentBacterial Infections / Skin Structures and Soft Tissue Infections2
3CompletedTreatmentCommunity Acquired Bacterial Pneumonia / Community Acquired Pneumonia (CAP)1
3CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
3CompletedTreatmentGestational Diabetes Mellitus as Antepartum Condition1
3CompletedTreatmentHealthcare-associated Pneumonia (HCAP) / Hospital-acquired bacterial pneumonia / Ventilator-associated Bacterial Pneumonia1
3CompletedTreatmentHospital Acquired Infections1
3CompletedTreatmentNeutropenia, Febrile1
3CompletedTreatmentPneumonia3
3CompletedTreatmentPneumonia, Bacterial1
3CompletedTreatmentSkin Diseases, Bacterial1
3CompletedTreatmentSkin Diseases, Bacterial / Skin Diseases, Infectious1
3CompletedTreatmentSkin Diseases, Infectious1
3CompletedTreatmentSkin Infections, Bacterial1
3CompletedTreatmentSkin and Subcutaneous Tissue Bacterial Infections3
3CompletedTreatmentAcute acute bacterial skin and skin structure infections2
3Not Yet RecruitingTreatmentBacterial Infections / Infections, Gram-Positive Bacterial / Mycobacterium Infections / Pulmonary Tuberculosis (TB) / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
3Not Yet RecruitingTreatmentSurgical Site Infections1
3RecruitingTreatmentDiabetes Mellitus (DM)1
3RecruitingTreatmentExtensively Drug Resistant Tuberculosis / Multi Drug Resistant Tuberculosis / Pre-XDR-TB / Rifampicin Resistant Tuberculosis / Tuberculosis Infection1
3RecruitingTreatmentExtensively Drug Resistant Tuberculosis / Multi-Drug Resistant Tuberculosis / Pre-XDR-TB / Pulmonary Tuberculosis (TB) / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
3RecruitingTreatmentStaphylococcus Aureus Infections1
3RecruitingTreatmentTuberculosis, Multidrug Resistant1
3RecruitingTreatmentHospital-acquired bacterial pneumonia / Ventilator-associated Bacterial Pneumonia1
3TerminatedNot AvailableOptic Nerve Diseases1
3TerminatedTreatmentBacteremia / Infections, Gram-Positive Bacterial1
3TerminatedTreatmentSkin Diseases, Infectious1
3WithdrawnTreatmentCommunity Acquired Pneumonia (CAP)1
3WithdrawnTreatmentSkin Structures and Soft Tissue Infections1
3WithdrawnTreatmentTuberculosis Multi Drug Resistant Active1
3WithdrawnTreatmentTuberculosis, Multidrug Resistant1
4CompletedNot AvailableComplicated Skin and Structure Infection / Hospital-acquired bacterial pneumonia1
4CompletedTreatmentDiabetes Mellitus (DM)1
4CompletedTreatmentInfections, Gram-Positive Bacterial / Skin and Connective Tissue Diseases1
4CompletedTreatmentMRSA Infection1
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA)1
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA) / Skin/Soft Tissue Infections1
4CompletedTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA)1
4CompletedTreatmentVentilator-Associated Pneumonia (VAP)1
4RecruitingNot AvailablePneumonia1
4RecruitingTreatmentCritical Illness / Mechanical Ventilation Complication1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedPreventionAcute acute bacterial skin and skin structure infections / Bacteremia / Endocarditis / Health Care Associated Pneumonia / Osteomyelitis/Septic Arthritis1
4Unknown StatusTreatmentBacteremia / Catheter Related Infections1
4Unknown StatusTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA) / Ventilator-Associated Pneumonia (VAP)1
4WithdrawnNot AvailableVentilator Acquired Pneumonia1
Not AvailableCompletedNot AvailableImpaired Renal Function / Renal Failure1
Not AvailableCompletedNot AvailableInfection caused by staphylococci1
Not AvailableCompletedNot AvailableInfections, Gram-Positive Bacterial1
Not AvailableCompletedNot AvailableMethicillin-Resistant Staphylococcus Aureus (MRSA) / Pneumonia, Hospital-Acquired1
Not AvailableCompletedNot AvailablePneumonia1
Not AvailableCompletedNot AvailableSepsis1
Not AvailableCompletedNot AvailableVancomycin Resistance Enterococcus Faecium1
Not AvailableCompletedOtherTuberculosis Infection1
Not AvailableCompletedTreatmentInfection caused by staphylococci / Infections, Gram-Positive Bacterial1
Not AvailableNot Yet RecruitingNot AvailableCerebral Hemorrhage / Subarachnoid Hemorrhage / Therapeutic Drug Monitoring1
Not AvailableRecruitingNot AvailableChildren;Infection1
Not AvailableRecruitingNot AvailableCritical Illness / Infection NOS1
Not AvailableRecruitingNot AvailableTuberculous Meningitis1
Not AvailableTerminatedNot AvailableAbscesses / Cellulitis / Erysipelas / Skin Diseases, Infectious / Wound Infections1
Not AvailableTerminatedTreatmentAbscesses / Skin Diseases, Bacterial1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
  • Fresenius Kabi AB
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Pfizer Inc.
  • Pharmacia Inc.
Dosage forms
FormRouteStrength
Injection, solutionIntravenous2 mg/1mL
Injection, solutionIntravenous200 mg/100mL
Injection, solutionIntravenous600 mg/300mL
PowderNot applicable1 kg/1kg
Powder, for suspensionOral100 mg/5mL
TabletOral600 mg/1
TabletOral600 mg
InjectionIntravenous600 mg/300mL
Injection, solutionIntravenous400 mg/200mL
SuspensionOral100 mg/5mL
Tablet, film coatedOral400 mg/1
Tablet, film coatedOral600 mg/1
Powder, for suspensionOral
SolutionIntravenous
TabletOral
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)
US5688792No1997-11-182014-11-18Us
CA2168560No2001-08-142014-08-16Canada
US6559305Yes2003-05-062021-07-29Us
US6514529Yes2003-02-042021-09-15Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9363
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.5881
P-glycoprotein inhibitor IInhibitor0.7599
P-glycoprotein inhibitor IINon-inhibitor0.6478
Renal organic cation transporterNon-inhibitor0.7469
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5904
CYP450 1A2 substrateNon-inhibitor0.7811
CYP450 2C9 inhibitorNon-inhibitor0.8174
CYP450 2D6 inhibitorNon-inhibitor0.8112
CYP450 2C19 inhibitorNon-inhibitor0.5664
CYP450 3A4 inhibitorNon-inhibitor0.7563
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5544
Ames testNon AMES toxic0.6839
CarcinogenicityNon-carcinogens0.8916
BiodegradationNot ready biodegradable0.9895
Rat acute toxicity2.4938 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7883
hERG inhibition (predictor II)Inhibitor0.6297
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

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

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxazinanes
Sub Class
Morpholines
Direct Parent
Phenylmorpholines
Alternative Parents
Aniline and substituted anilines / Dialkylarylamines / Fluorobenzenes / Oxazolidinones / Aryl fluorides / Acetamides / Carbamate esters / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Dialkyl ethers
show 7 more
Substituents
Phenylmorpholine / Aniline or substituted anilines / Tertiary aliphatic/aromatic amine / Dialkylarylamine / Fluorobenzene / Halobenzene / Aryl fluoride / Aryl halide / Monocyclic benzene moiety / Oxazolidinone
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, acetamides, morpholines, oxazolidinone (CHEBI:63607)

Targets

Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.
References
  1. 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
Humans
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...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Stevens DL, Dotter B, Madaras-Kelly K: A review of linezolid: the first oxazolidinone antibiotic. Expert Rev Anti Infect Ther. 2004 Feb;2(1):51-9. [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
Humans
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...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Stevens DL, Dotter B, Madaras-Kelly K: A review of linezolid: the first oxazolidinone antibiotic. Expert Rev Anti Infect Ther. 2004 Feb;2(1):51-9. [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]

Drug created on June 13, 2005 07:24 / Updated on November 16, 2019 10:25