R-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-CYBMUJFWSA-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-/m1/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 8228		116.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Nosocomial pneumonia 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf	Curative	Approved 8360	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
Community-acquired pneumonia 47 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf	Curative	Approved 8360	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
Skin infections 55 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf	Curative	Approved 8360	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
Vancomycin-resistant Enterococcus faecium infections 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206473s000lbl.pdf	Curative	Approved 8360	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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1579 substrate 1709	inhibitor 1752 inducer 383	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2C19 1463 CYP2E1 876		CYP1A 56 CYP2B 32 CYP2C 15 CYP2E1 126 CYP3A 126 CYP4A 14

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A 121	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2B 40	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C 34	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2E1 964	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP3A 295	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP3A4 1909	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP4A 33	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C9 1803	inducer 1542 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 1803	inhibitor 3240 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 1709	substrate 3326 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
LGC Standards	MM3300.07-0025	https://www.lgcstandards.com/US/en/p/MM3300.07-0025
Lab Network	LN00798992	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00798992
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
iChemical	EBD4029009	http://www.ichemical.com/products/872992-20-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-7828732421	https://mcule.com/MCULE-7828732421/

PubMed

Title	Date	PubMed
[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
Linezolid absolute bioavailability and the effect of food on oral bioavailability.	2001 Apr	11745911
Hematologic effects of antimicrobials: focus on the oxazolidinone linezolid.	2001 Aug	11718489
Antimicrobial activity of linezolid against Gram-positive cocci isolated in Brazil.	2001 Aug	11712961
Linezolid treatment of prosthetic hip Infections due to methicillin-resistant Staphylococcus aureus (MRSA).	2001 Aug	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 Aug	11576790
New anti-Gram-positive agents.	2001 Aug	11571419
Pneumonia and sepsis due to fluoroquinolone-resistant Capnocytophaga gingivalis after autologous stem cell transplantation.	2001 Dec	11803363
Successful treatment of vancomycin-resistant enterococcus meningitis with linezolid: case report and review of the literature.	2001 Dec	11801846
In vitro activity of linezolid against Gram-positive cocci isolated in Poland.	2001 Dec	11733485
Linezolid levels in pancreatic secretions.	2001 Dec	11733483
Comparative activity of linezolid and other new agents against methicillin-resistant Staphylococcus aureus and teicoplanin-intermediate coagulase-negative staphylococci.	2001 Dec	11733478
Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria.	2001 Dec	11711300
Oxazolidinone antibiotics.	2001 Dec 8	11747939
Combinatorial lead discovery and optimization of antimicrobial oxazolidinones.	2001 Jul	11727310
Ciprofloxacin- and methicillin-resistant staphylococcus aureus susceptible to moxifloxacin, levofloxacin, teicoplanin, vancomycin and linezolid.	2001 Jul	11561805
[Ribosomal antibiotics].	2001 Jul-Aug	11524946
Linezolid: a new antibiotic for gram-positive infections.	2001 Nov	11762099
Pharmacodynamics of antiinfective therapy: taking what we know to the patient's bedside.	2001 Nov	11714223
A simple, isocratic high-performance liquid chromatography assay for linezolid in human serum.	2001 Nov	11679548
NCCN: Fever and neutropenia.	2001 Nov-Dec	11760554
In vitro antimicrobial activity of linezolid tested against vancomycin-resistant enterococci isolated in Brazilian hospitals.	2001 Oct	11779450
Oxazolidinones: a new class of antibacterials.	2001 Oct	11764772
Clinical experience with linezolid in the treatment of resistant gram-positive infections.	2001 Oct	11688919
Activity of linezolid against levofloxacin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci in Hong Kong.	2001 Oct	11581246
Linezolid for treatment of vancomycin-resistant enterococcal peritonitis.	2001 Oct	11576907
Successful treatment of disseminated Mycobacterium chelonae infection with linezolid.	2001 Oct 15	11550122
Linezolid and reversible myelosuppression.	2001 Oct 24-31	11667931
Linezolid and reversible myelosuppression.	2001 Oct 24-31	11667930
Linezolid and reversible myelosuppression.	2001 Oct 24-31	11667929
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	11714042
The DUEL study: a multi-center in vitro evaluation of linezolid compared with other antibiotics in the Netherlands.	2001 Sep	11678931
In vitro activity of linezolid against clinical Gram-positive bacterial isolates from Taiwan: an area with a high prevalence of antibiotic resistance.	2001 Sep	11673041
In vitro activity of linezolid against Gram-positive uropathogens of hospitalized patients with complicated urinary tract infections.	2001 Sep	11673040
Determination of linezolid in human serum and urine by high-performance liquid chromatography.	2001 Sep	11673038
Susceptibility testing with linezolid by different methods, in relation to published 'general breakpoints'.	2001 Sep	11533020
Linezolid and serotonin syndrome.	2001 Sep-Oct	11739912
Treatment options for vancomycin-resistant enterococcal infections.	2002	11827558
Linezolid-resistant Enterococcus faecium isolated from a patient without prior exposure to an oxazolidinone: report from the SENTRY Antimicrobial Surveillance Program.	2002 Feb	11858910
In vitro evaluation of AZD2563, a new oxazolidinone, tested against unusual gram-positive species.	2002 Feb	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 Feb	11837547
An investigation of the antimicrobial effects of linezolid on bacterial biofilms utilizing an in vitro pharmacokinetic model.	2002 Feb	11815571
[Significance of antibiotic resistance in treatment of soft tissue infections].	2002 Jan	11851046
Linezolid-Induced anemia and thrombocytopenia.	2002 Jan	11794421
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.	2002 Mar	11850285
Successful treatment of methicillin-resistant Staphylococcus aureus pulmonary infection with linezolid in a patient with cystic fibrosis.	2002 Mar	11836802
Thrombocytopenia associated with linezolid therapy.	2002 Mar 1	11803505

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 `Thu Jul 06 20:15:39 UTC 2023` Edited by `admin` on `Thu Jul 06 20:15:39 UTC 2023`
Record UNII	4H12RJ0A6E
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

R-LINEZOLID

Common Name

English

LINEZOLID R-ISOMER

Common Name

English

(R)-LINEZOLID

Common Name

English

LINEZOLID R-ISOMER [USP-RS]

Common Name

English

ACETAMIDE, N-(((5R)-3-(3-FLUORO-4-(4-MORPHOLINYL)PHENYL)-2-OXO-5-OXAZOLIDINYL)METHYL)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID70275723