LINEZOLID

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021130s030,021131s029,021132s034lbl.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
70S ribosome 16 Target ID: CHEMBL2363853 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021130s030,021131s029,021132s034lbl.pdf	Inhibitor 8504		116.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Nosocomial pneumonia 10 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf	Curative	Approved 8583	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
Community-acquired pneumonia 47 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf	Curative	Approved 8583	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
Skin infections 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf	Curative	Approved 8583	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
Vancomycin-resistant Enterococcus faecium infections 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf	Curative	Approved 8583	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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	inhibitor 2438 inducer 440	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 CYP2E1 1060		CYP1A 59 CYP2B 32 CYP2C 17 CYP2E1 131 CYP3A 142 CYP4A 14

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A 122	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2B 41	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C 37	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2E1 1146	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP3A 317	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP4A 34	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=8 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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=8 Page: 8.0
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=21 Page: 21.0	yes

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	AP872992206	https://reagents.alfa-chemistry.com/product/linezolid-r-isomer-cas-872992-20-6-17652.html
Aurora Fine Chemicals LLC	A12.866.671	http://online.aurorafinechemicals.com/info?ID=A12.866.671
BLD Pharm	BD01140282	http://www.bldpharm.com/products/872992-20-6.html
Boerchem	BC666140	http://www.boerchem.com/?product_39118.html
Chem Scene	CS-0112395	http://www.chemscene.com/872992-20-6.html
ChemMol	30103059	http://www.chemmol.com/chemmol/30103059.html
ChemMol	44002426	http://www.chemmol.com/chemmol/44002426.html
ChemMol	49409198	http://www.chemmol.com/chemmol/49409198.html
Chemspace	CSSB00020654749	https://chem-space.com/CSSB00020654749
iChemical	EBD4029009	http://www.ichemical.com/products/872992-20-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00798992	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00798992
LGC Standards	MM3300.07-0025	https://www.lgcstandards.com/US/en/p/MM3300.07-0025
mcule	MCULE-7828732421	https://mcule.com/MCULE-7828732421/
MedChem Express	HY-135397	https://www.medchemexpress.com/r-linezolid.html
MuseChem	R057539	https://www.musechem.com/product/R057539.html
Renno Tech	RP17818	http://www.rennotech.com/product_show.asp?id=23696
THE BioTek	bt-297755	https://www.thebiotek.com/product/others/bt-297755
Yuhao Chemical	RT5956	http://www.chemyuhao.com/872992-20-6.html

PubMed

Title	Date	PubMed
Thrombocytopenia associated with linezolid therapy.	2002-03-01	11803505
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.	2002-03	11850285
Successful treatment of methicillin-resistant Staphylococcus aureus pulmonary infection with linezolid in a patient with cystic fibrosis.	2002-03	11836802
Linezolid-resistant Enterococcus faecium isolated from a patient without prior exposure to an oxazolidinone: report from the SENTRY Antimicrobial Surveillance Program.	2002-02	11858910
In vitro evaluation of AZD2563, a new oxazolidinone, tested against unusual gram-positive species.	2002-02	11858907
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.	2002-02	11837547
An investigation of the antimicrobial effects of linezolid on bacterial biofilms utilizing an in vitro pharmacokinetic model.	2002-02	11815571
NCCN: Fever and neutropenia.	2002-01-05	11760554
[Significance of antibiotic resistance in treatment of soft tissue infections].	2002-01	11851046
Linezolid-Induced anemia and thrombocytopenia.	2002-01	11794421
Treatment options for vancomycin-resistant enterococcal infections.	2002	11827558
Linezolid and serotonin syndrome.	2001-12-12	11739912
Oxazolidinone antibiotics.	2001-12-08	11747939
Pneumonia and sepsis due to fluoroquinolone-resistant Capnocytophaga gingivalis after autologous stem cell transplantation.	2001-12	11803363
Successful treatment of vancomycin-resistant enterococcus meningitis with linezolid: case report and review of the literature.	2001-12	11801846
In vitro activity of linezolid against Gram-positive cocci isolated in Poland.	2001-12	11733485
Linezolid levels in pancreatic secretions.	2001-12	11733483
Comparative activity of linezolid and other new agents against methicillin-resistant Staphylococcus aureus and teicoplanin-intermediate coagulase-negative staphylococci.	2001-12	11733478
Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria.	2001-12	11711300
Linezolid and reversible myelosuppression.	2001-11-03	11667931
Linezolid and reversible myelosuppression.	2001-11-03	11667930
Linezolid and reversible myelosuppression.	2001-11-03	11667929
Linezolid: a new antibiotic for gram-positive infections.	2001-11	11762099
Pharmacodynamics of antiinfective therapy: taking what we know to the patient's bedside.	2001-11	11714223
A simple, isocratic high-performance liquid chromatography assay for linezolid in human serum.	2001-11	11679548
Successful treatment of disseminated Mycobacterium chelonae infection with linezolid.	2001-10-15	11550122
In vitro antimicrobial activity of linezolid tested against vancomycin-resistant enterococci isolated in Brazilian hospitals.	2001-10	11779450
Oxazolidinones: a new class of antibacterials.	2001-10	11764772
Clinical experience with linezolid in the treatment of resistant gram-positive infections.	2001-10	11688919
Activity of linezolid against levofloxacin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci in Hong Kong.	2001-10	11581246
Linezolid for treatment of vancomycin-resistant enterococcal peritonitis.	2001-10	11576907
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.	2001-09	11714042
The DUEL study: a multi-center in vitro evaluation of linezolid compared with other antibiotics in the Netherlands.	2001-09	11678931
In vitro activity of linezolid against clinical Gram-positive bacterial isolates from Taiwan: an area with a high prevalence of antibiotic resistance.	2001-09	11673041
In vitro activity of linezolid against Gram-positive uropathogens of hospitalized patients with complicated urinary tract infections.	2001-09	11673040
Determination of linezolid in human serum and urine by high-performance liquid chromatography.	2001-09	11673038
Susceptibility testing with linezolid by different methods, in relation to published 'general breakpoints'.	2001-09	11533020
[Ribosomal antibiotics].	2001-08-30	11524946
Hematologic effects of antimicrobials: focus on the oxazolidinone linezolid.	2001-08	11718489
Antimicrobial activity of linezolid against Gram-positive cocci isolated in Brazil.	2001-08	11712961
Linezolid treatment of prosthetic hip Infections due to methicillin-resistant Staphylococcus aureus (MRSA).	2001-08	11676523
In vitro antimicrobial activity of GAR-936 tested against antibiotic-resistant gram-positive blood stream infection isolates and strains producing extended-spectrum beta-lactamases.	2001-08	11576790
New anti-Gram-positive agents.	2001-08	11571419
Combinatorial lead discovery and optimization of antimicrobial oxazolidinones.	2001-07	11727310
Ciprofloxacin- and methicillin-resistant staphylococcus aureus susceptible to moxifloxacin, levofloxacin, teicoplanin, vancomycin and linezolid.	2001-07	11561805
Linezolid absolute bioavailability and the effect of food on oral bioavailability.	2001-04	11745911
[Methicillin-resistant Staphylococcus aureus--the pathogen].	2001	11824353
Linezolid: pharmacokinetic characteristics and clinical studies.	2001	11688537
The oxazolidinones as a new family of antimicrobial agent.	2001	11688536
Quinupristin/dalfopristin and linezolid: spectrum of activity and potential roles in therapy--a status report.	2001	11572153

Patents

Sample Use Guides

In Vivo Use Guide

600 mg every 12 hours

Route of Administration: Other

In Vitro Use Guide

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 `Mon Mar 31 18:07:38 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:38 GMT 2025`
Record UNII	ISQ9I6J12J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LINEZOLID

Official Name

English

ZYVOX

Preferred 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

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