U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20FN3O4
Molecular Weight 337.3461
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LINEZOLID

SMILES

CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC=C(N3CCOCC3)C(F)=C2

InChI

InChIKey=TYZROVQLWOKYKF-ZDUSSCGKSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc3e3ea4-50aa-49ee-a8bc-fb48bfc8e014

Linezolid is an antibiotic used for the treatment of infections caused by Gram-positive bacteria that are resistant to other antibiotics. Linezolid appears to be unique in that it blocks the initiation of protein production. Most common adverse reactions include diarrhea, vomiting, headache, nausea, and anemia. Linezolid has the potential for interaction with adrenergic and serotonergic agents. And with monoamine oxidase inhibitors because it’s nonselective inhibitor of monoamine oxidase.

Originator

Curator's Comment: Linezolid was discovered in the 1990s by a team at Pharmacia and Upjohn Company. http://www.google.com/patents/US5688792

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
116.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ZYVOX

Approved Use

ZYVOX is indicated for the treatment of Nosocomial pneumonia caused by Staphylococcus aureus (methicillin-susceptible and -resistant isolates) or Streptococcus pneumoniae.

Launch Date

2000
Curative
ZYVOX

Approved Use

ZYVOX is indicated for the treatment of Community-acquired pneumonia caused by Streptococcus pneumoniae, including cases with concurrent bacteremia, or Staphylococcus aureus (methicillin-susceptible isolates only).

Launch Date

2000
Curative
ZYVOX

Approved Use

ZYVOX is indicated for the treatment of Complicated skin and skin structure infections, including diabetic foot infections, without concomitant osteomyelitis, caused by Staphylococcus aureus (methicillin-susceptible and -resistant isolates), Streptococcus pyogenes, or Streptococcus agalactiae.

Launch Date

2000
Curative
ZYVOX

Approved Use

ZYVOX is indicated for the treatment of infections Vancomycin-resistant Enterococcus faecium infections, including cases with concurrent bacteremia.

Launch Date

2000
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no (co-administration study)
Comment: Concurrent administration of linezolid does not substantially alter the pharmacokinetic characteristics of (S)-warfarin, which is extensively metabolized by CYP2C9.
Page: 8.0
no
no (co-administration study)
Comment: Concurrent administration of linezolid does not substantially alter the pharmacokinetic characteristics of (S)-warfarin, which is extensively metabolized by CYP2C9.
Page: 20.0
Drug as victim
PubMed

PubMed

TitleDatePubMed
Oxazolidinones: a review.
2000 Jan
[Methicillin-resistant Staphylococcus aureus--the pathogen].
2001
The oxazolidinones as a new family of antimicrobial agent.
2001
Quinupristin/dalfopristin and linezolid: spectrum of activity and potential roles in therapy--a status report.
2001
Linezolid absolute bioavailability and the effect of food on oral bioavailability.
2001 Apr
Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents. 3. Synthesis and evaluation of 5-thiocarbamate oxazolidinones.
2001 Apr
Antimicrobial management strategies for Gram-positive bacterial resistance in the intensive care unit.
2001 Apr
Hematologic effects of antimicrobials: focus on the oxazolidinone linezolid.
2001 Aug
Antimicrobial activity of linezolid against Gram-positive cocci isolated in Brazil.
2001 Aug
In vitro antimicrobial activity of GAR-936 tested against antibiotic-resistant gram-positive blood stream infection isolates and strains producing extended-spectrum beta-lactamases.
2001 Aug
New anti-Gram-positive agents.
2001 Aug
Pharmacokinetics, metabolism, and excretion of linezolid following an oral dose of [(14)C]linezolid to healthy human subjects.
2001 Aug
Vancomycin-resistant Enterococcus faecium meningitis successfully managed with linezolid: case report and review of the literature.
2001 Aug 15
Pneumonia and sepsis due to fluoroquinolone-resistant Capnocytophaga gingivalis after autologous stem cell transplantation.
2001 Dec
Successful treatment of vancomycin-resistant enterococcus meningitis with linezolid: case report and review of the literature.
2001 Dec
Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria.
2001 Dec
Oxazolidinone antibiotics.
2001 Dec 8
Linezolid therapy of vancomycin-resistant Enterococcus faecium experimental endocarditis.
2001 Feb
In vitro activity of linezolid against multiply resistant Gram-positive clinical isolates.
2001 Jan
Ciprofloxacin- and methicillin-resistant staphylococcus aureus susceptible to moxifloxacin, levofloxacin, teicoplanin, vancomycin and linezolid.
2001 Jul
Linezolid for gram-positive infections.
2001 Jul
[Ribosomal antibiotics].
2001 Jul-Aug
What do the new antimicrobials offer? Weighing the advantages and disadvantages compared with traditional agents.
2001 Mar
Compatibility of linezolid injection with intravenous administration sets.
2001 Mar-Apr
Linezolid breakpoints.
2001 May
Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine.
2001 May
Linezolid for the treatment of resistant gram-positive cocci.
2001 May
Cardiovascular sympathomimetic amine interactions in rats treated with monoamine oxidase inhibitors and the novel oxazolidinone antibiotic linezolid.
2001 May
Successful treatment of vancomycin-resistant Enterococcus endocarditis with oral linezolid.
2001 May 1
Linezolid: a new antibiotic for gram-positive infections.
2001 Nov
Pharmacodynamics of antiinfective therapy: taking what we know to the patient's bedside.
2001 Nov
A simple, isocratic high-performance liquid chromatography assay for linezolid in human serum.
2001 Nov
NCCN: Fever and neutropenia.
2001 Nov-Dec
In vitro antimicrobial activity of linezolid tested against vancomycin-resistant enterococci isolated in Brazilian hospitals.
2001 Oct
Oxazolidinones: a new class of antibacterials.
2001 Oct
Activity of linezolid against levofloxacin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci in Hong Kong.
2001 Oct
Successful treatment of disseminated Mycobacterium chelonae infection with linezolid.
2001 Oct 15
Frequency of isolation and antimicrobial resistance of gram-negative and gram-positive bacteria from patients in intensive care units of 25 European university hospitals participating in the European arm of the SENTRY Antimicrobial Surveillance Program 1997-1998.
2001 Sep
In vitro activity of linezolid against Gram-positive uropathogens of hospitalized patients with complicated urinary tract infections.
2001 Sep
Susceptibility testing with linezolid by different methods, in relation to published 'general breakpoints'.
2001 Sep
Treatment options for vancomycin-resistant enterococcal infections.
2002
Linezolid-resistant Enterococcus faecium isolated from a patient without prior exposure to an oxazolidinone: report from the SENTRY Antimicrobial Surveillance Program.
2002 Feb
In vitro evaluation of AZD2563, a new oxazolidinone, tested against unusual gram-positive species.
2002 Feb
Approaches to analysis of length of hospital stay related to antibiotic therapy in a randomized clinical trial: linezolid versus vancomycin for treatment of known or suspected methicillin-resistant Staphylococcus species infections.
2002 Feb
An investigation of the antimicrobial effects of linezolid on bacterial biofilms utilizing an in vitro pharmacokinetic model.
2002 Feb
[Significance of antibiotic resistance in treatment of soft tissue infections].
2002 Jan
Linezolid-Induced anemia and thrombocytopenia.
2002 Jan
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.
2002 Mar
Successful treatment of methicillin-resistant Staphylococcus aureus pulmonary infection with linezolid in a patient with cystic fibrosis.
2002 Mar
Thrombocytopenia associated with linezolid therapy.
2002 Mar 1
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Injection: 600 mg every 12 hours Linezolid solution is available in 200, 400, 600 mg. Oral suspensions - 100 mg.
600 mg every 12 hours
Route of Administration: Other
Linezolid was tested against 32 species of uncommonly isolated gram-positive organisms (3,251 strains) by reference MIC methods and found to be highly active (MIC50 range, 0.25 to 2 microg/ml; MIC90 range, 0.25 to 2 microg/ml).
Name Type Language
LINEZOLID
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
U-100766
Code English
LINEZOLID [USP-RS]
Common Name English
LINEZOLID [USAN]
Common Name English
LINEZOLID [MART.]
Common Name English
Linezolid [WHO-DD]
Common Name English
LINEZOLID [VANDF]
Common Name English
ZYVOX
Brand Name English
LINEZOLID [MI]
Common Name English
LINEZOLID [HSDB]
Common Name English
PNU-100766
Common Name English
LINEZOLID [ORANGE BOOK]
Common Name English
LINEZOLID [USP MONOGRAPH]
Common Name English
N-[[(S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide
Systematic Name English
U-100,766
Code English
linezolid [INN]
Common Name English
LINEZOLID [JAN]
Common Name English
ACETAMIDE, N-((3-(3-FLUORO-4-(4-MORPHOLINYL)PHENYL)-2-OXO-5-OXAZOLIDINYL)METHYL)-, (S)-
Common Name English
Classification Tree Code System Code
NDF-RT N0000007568
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
LIVERTOX NBK548245
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
NDF-RT N0000175495
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
NCI_THESAURUS C258
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
WHO-VATC QJ01XX08
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
WHO-ATC J01XX08
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
Code System Code Type Description
INN
7584
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
DRUG BANK
DB00601
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
DAILYMED
ISQ9I6J12J
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
NCI_THESAURUS
C29158
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
ChEMBL
CHEMBL126
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
FDA UNII
ISQ9I6J12J
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID5046489
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
EVMPD
SUB08520MIG
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
CHEBI
63607
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
MERCK INDEX
m6829
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY Merck Index
RXCUI
190376
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY RxNorm
CAS
165800-03-3
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
SMS_ID
100000092506
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
MESH
C098010
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
RS_ITEM_NUM
1367561
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
PUBCHEM
441401
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
DRUG CENTRAL
1584
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
HSDB
7478
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
LACTMED
Linezolid
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
WIKIPEDIA
LINEZOLID
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY
USAN
II-7
Created by admin on Fri Dec 15 15:45:32 GMT 2023 , Edited by admin on Fri Dec 15 15:45:32 GMT 2023
PRIMARY