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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20FN3O4
Molecular Weight 337.3467
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LINEZOLID

SMILES

CC(=NC[C@@]1([H])CN(c2ccc(c(c2)F)N3CCOCC3)C(=O)O1)O

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

Molecular Formula C16H20FN3O4
Molecular Weight 337.3467
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

9.5601597E11
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

9.5601597E11
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

9.5601597E11
Curative
ZYVOX

Approved Use

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

Launch Date

9.5601597E11
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
Linezolid: pharmacokinetic characteristics and clinical studies.
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
Successful treatment of vancomycin-resistant Enterococcus faecium meningitis with linezolid: case report and literature review.
2001
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
In vitro activity of fosfomycin in combination with various antistaphylococcal substances.
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
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
Combinatorial lead discovery and optimization of antimicrobial oxazolidinones.
2001 Jul
Ciprofloxacin- and methicillin-resistant staphylococcus aureus susceptible to moxifloxacin, levofloxacin, teicoplanin, vancomycin and linezolid.
2001 Jul
Susceptibility of a variety of clinical isolates to linezolid: a European inter-country comparison.
2001 Jul
Linezolid for gram-positive infections.
2001 Jul
Antimicrobial susceptibility patterns of enterococci in intensive care units in Sweden evaluated by different MIC breakpoint systems.
2001 Jul
Linezolid resistance in a clinical isolate of Staphylococcus aureus.
2001 Jul 21
[Ribosomal antibiotics].
2001 Jul-Aug
Successful treatment of vancomycin-resistant Enterococcus meningitis with linezolid.
2001 Jun
Systemic and intracerebral infections of mice with Listeria monocytogenes successfully treated with linezolid.
2001 Jun
Microbial drug resistance and the roles of the new antibiotics.
2001 Jun
Methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci: emerging problems and new prospects for management.
2001 May
Linezolid breakpoints.
2001 May
Multi-laboratory assessment of the linezolid spectrum of activity using the Kirby-Bauer disk diffusion method: Report of the Zyvox Antimicrobial Potency Study (ZAPS) in the United States.
2001 May-Jun
Pharmacodynamics of antiinfective therapy: taking what we know to the patient's bedside.
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
Clinical experience with linezolid in the treatment of resistant gram-positive infections.
2001 Oct
Activity of linezolid against levofloxacin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci in Hong Kong.
2001 Oct
Linezolid for treatment of vancomycin-resistant enterococcal peritonitis.
2001 Oct
Successful treatment of disseminated Mycobacterium chelonae infection with linezolid.
2001 Oct 15
Linezolid and reversible myelosuppression.
2001 Oct 24-31
Linezolid and reversible myelosuppression.
2001 Oct 24-31
Linezolid and reversible myelosuppression.
2001 Oct 24-31
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
Determination of linezolid in human serum and urine by high-performance liquid chromatography.
2001 Sep
Susceptibility testing with linezolid by different methods, in relation to published 'general breakpoints'.
2001 Sep
Does the dose matter?
2001 Sep 15
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
[Significance of antibiotic resistance in treatment of soft tissue infections].
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).
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:27:24 UTC 2021
Edited
by admin
on Fri Jun 25 21:27:24 UTC 2021
Record UNII
ISQ9I6J12J
Record Status Validated (UNII)
Record Version
  • Download
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 [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 [WHO-DD]
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 Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
LIVERTOX 560
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
NDF-RT N0000175495
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
NCI_THESAURUS C258
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
WHO-VATC QJ01XX08
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
WHO-ATC J01XX08
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
Code System Code Type Description
INN
7584
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
DRUG BANK
DB00601
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
NCI_THESAURUS
C29158
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
ChEMBL
CHEMBL126
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
FDA UNII
ISQ9I6J12J
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
EPA CompTox
165800-03-3
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
EVMPD
SUB08520MIG
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
MERCK INDEX
M6829
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY Merck Index
RXCUI
190376
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY RxNorm
CAS
165800-03-3
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
MESH
C098010
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
PUBCHEM
441401
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
USP_CATALOG
1367561
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
1584
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
HSDB
7478
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
LACTMED
Linezolid
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
WIKIPEDIA
LINEZOLID
Created by admin on Fri Jun 25 21:27:25 UTC 2021 , Edited by admin on Fri Jun 25 21:27:25 UTC 2021
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE -> PARENT
Accounted for less than 0.1% of the dose (Trace level). Presumed to involve N-acetyltransferase; reversible
METABOLITE -> PARENT
PARTIAL AGONIST
FECAL; PLASMA; URINE
METABOLITE INACTIVE -> PARENT
minor in plasma
MAJOR
FECAL; URINE
METABOLITE -> PARENT
approximately 0.4 to 0.8% of the dose (trace level)
METABOLITE -> PARENT
MINOR
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC POPULATION: ADULTS

Biological Half-life PHARMACOKINETIC POPULATION: FULL-TERM NEONATES ? 1 WEEK TO ? 28 DAYS

Volume of Distribution PHARMACOKINETIC POPULATION: INFANTS > 28 DAYS TO < 3 MONTHS

Biological Half-life PHARMACOKINETIC POPULATION: INFANTS > 28 DAYS TO < 3 MONTHS

Volume of Distribution PHARMACOKINETIC POPULATION: ADULTS

Volume of Distribution PHARMACOKINETIC POPULATION: INFANTS AND CHILDREN 3 MONTHS TO 11 YEARS

ORAL BIOAVAILABILITY PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC POPULATION: ADOLESCENTS

Volume of Distribution PHARMACOKINETIC POPULATION: ADOLESCENTS

Biological Half-life PHARMACOKINETIC POPULATION: ADULTS

Biological Half-life PHARMACOKINETIC POPULATION: FULL-TERM NEONATES < 1 WEEK

Volume of Distribution PHARMACOKINETIC POPULATION: FULL-TERM NEONATES ? 1 WEEK TO ? 28 DAYS

Volume of Distribution PHARMACOKINETIC POPULATION: FULL-TERM NEONATES < 1 WEEK

Biological Half-life PHARMACOKINETIC POPULATION: FULL-TERM NEONATES < 1 WEEK

Volume of Distribution PHARMACOKINETIC POPULATION: PRETERM NEONATES < 1 WEEK

Vdss PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC POPULATION: INFANTS AND CHILDREN 3 MONTHS TO 11 YEARS