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

Molecular Formula C16H20FN3O4
Molecular Weight 337.3461
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

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
Activities of several novel oxazolidinones against Mycobacterium tuberculosis in a murine model.
1999 May
The oxazolidinones as a new family of antimicrobial agent.
2001
Successful treatment of vancomycin-resistant Enterococcus faecium meningitis with linezolid: case report and literature review.
2001
Linezolid: a review of its use in the management of serious gram-positive infections.
2001
Linezolid absolute bioavailability and the effect of food on oral bioavailability.
2001 Apr
Infections due to vancomycin-resistant Enterococcus faecium resistant to linezolid.
2001 Apr 14
Antimicrobial activity of linezolid against Gram-positive cocci isolated in Brazil.
2001 Aug
New anti-Gram-positive agents.
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
In vitro activity of linezolid against Gram-positive cocci isolated in Poland.
2001 Dec
Linezolid therapy of vancomycin-resistant Enterococcus faecium experimental endocarditis.
2001 Feb
[Multiresistant tuberculosis caused by Mycobacterium bovis and human immunodeficiency virus infection. Are there new therapeutic possibilities?].
2001 Jan
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
Microbial drug resistance and the roles of the new antibiotics.
2001 Jun
Post-antibiotic growth suppression of linezolid against Gram-positive bacteria.
2001 Jun
Linezolid: an oxazolidinone antimicrobial agent.
2001 Mar
Efficacy of linezolid in a staphylococcal endocarditis rabbit model.
2001 Mar
Linezolid and reversible myelosuppression.
2001 Mar 14
Compatibility of linezolid injection with intravenous administration sets.
2001 Mar-Apr
Methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci: emerging problems and new prospects for management.
2001 May
Linezolid for the treatment of resistant gram-positive cocci.
2001 May
Linezolid: a new antibiotic for gram-positive infections.
2001 Nov
Activity of linezolid against levofloxacin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci in Hong Kong.
2001 Oct
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
Linezolid and serotonin syndrome.
2001 Sep-Oct
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
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
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 Dec 15 15:45:32 GMT 2023
Edited
by admin
on Fri Dec 15 15:45:32 GMT 2023
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 [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
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC POPULATION: ADULTS

Tmax PHARMACOKINETIC
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