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 8297		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 8429	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 8429	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 8429	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 8429	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 1587 substrate 1737	inhibitor 1767 inducer 389	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP2E1 882		CYP1A 56 CYP2B 32 CYP2C 15 CYP2E1 128 CYP3A 129 CYP4A 14

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A 121	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2B 40	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C 34	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP2E1 970	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP3A 298	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021130s039s040,021131s034s035,021132s038s039lbl.pdf#page=20 Page: 20.0	no
CYP4A 33	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21130_Zyvox_biopharmr.pdf#page=3 Page: 3.0	no
CYP2C9 1819	inducer 1573 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 1819	inhibitor 3277 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 1737	substrate 3367 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
Linezolid: pharmacokinetic characteristics and clinical studies.	2001	11688537
Linezolid: a review of its use in the management of serious gram-positive infections.	2001	11324682
Linezolid absolute bioavailability and the effect of food on oral bioavailability.	2001 Apr	11745911
Infections due to vancomycin-resistant Enterococcus faecium resistant to linezolid.	2001 Apr 14	11323048
Hematologic effects of antimicrobials: focus on the oxazolidinone linezolid.	2001 Aug	11718489
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
In vitro activity of fosfomycin in combination with various antistaphylococcal substances.	2001 Aug	11481290
Pharmacokinetics, metabolism, and excretion of linezolid following an oral dose of [(14)C]linezolid to healthy human subjects.	2001 Aug	11454733
Vancomycin-resistant Enterococcus faecium meningitis successfully managed with linezolid: case report and review of the literature.	2001 Aug 15	11462183
Comparative activity of linezolid and other new agents against methicillin-resistant Staphylococcus aureus and teicoplanin-intermediate coagulase-negative staphylococci.	2001 Dec	11733478
Oxazolidinone antibiotics.	2001 Dec 8	11747939
Susceptibility of a variety of clinical isolates to linezolid: a European inter-country comparison.	2001 Jul	11474632
Linezolid for gram-positive infections.	2001 Jul	11471517
Linezolid resistance in a clinical isolate of Staphylococcus aureus.	2001 Jul 21	11476839
[Ribosomal antibiotics].	2001 Jul-Aug	11524946
Successful treatment of vancomycin-resistant Enterococcus meningitis with linezolid.	2001 Jun	11476449
Systemic and intracerebral infections of mice with Listeria monocytogenes successfully treated with linezolid.	2001 Jun	11450884
Microbial drug resistance and the roles of the new antibiotics.	2001 Jun	11405611
Post-antibiotic growth suppression of linezolid against Gram-positive bacteria.	2001 Jun	11389123
[In vitro activity of linezolid against clinical isolates of methicillin-resistant Staphylococcus aureus].	2001 Mar	11376349
Linezolid: an oxazolidinone antimicrobial agent.	2001 Mar	11318073
Methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci: emerging problems and new prospects for management.	2001 May	11455748
Determination of linezolid in human plasma by LC-MS-MS.	2001 May	11394301
Linezolid for the treatment of community-acquired pneumonia in hospitalized children. Linezolid Pediatric Pneumonia Study Group.	2001 May	11368105
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.	2001 May	11361053
Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine.	2001 May	11361052
Linezolid for the treatment of resistant gram-positive cocci.	2001 May	11346064
Cardiovascular sympathomimetic amine interactions in rats treated with monoamine oxidase inhibitors and the novel oxazolidinone antibiotic linezolid.	2001 May	11336106
In vitro activity of linezolid and 11 other antimicrobials against 566 clinical isolates and comparison between NCCLS microdilution and Etest methods.	2001 May	11328783
A new and rapid method for monitoring the new oxazolidinone antibiotic linezolid in serum and urine by high performance liquid chromatography-integrated sample preparation.	2001 May 5	11393729
Researchers describe latest strategies to combat antibiotic-resistant microbes.	2001 May 9	11343462
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	11448565
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
NCCN: Fever and neutropenia.	2001 Nov-Dec	11760554
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
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
Does the dose matter?	2001 Sep 15	11524724
Linezolid and serotonin syndrome.	2001 Sep-Oct	11739912
Linezolid-resistant Enterococcus faecium isolated from a patient without prior exposure to an oxazolidinone: report from the SENTRY Antimicrobial Surveillance Program.	2002 Feb	11858910
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
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

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 `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

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Name

Type

Language

LINEZOLID

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