Linezolid | CAS#165800-03-3 | Antibiotic

MedKoo Cat#: 318153 | Name: Linezolid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Linezolid, also known as PNU-100766, is a synthetic oxazolidinone antibiotic active against a wide range of Gram-positive bacteria, including resistant strains of several species, such as MRSA and penicillin-resistant pneumococci. Linezolid inhibits protein synthesis by binding to domain V of the 23S ribosomal RNA of the 50S subunit of bacterial ribosomes.

Chemical Structure

Linezolid

CAS#165800-03-3

Theoretical Analysis

MedKoo Cat#: 318153

Name: Linezolid

CAS#: 165800-03-3

Chemical Formula: C16H20FN3O4

Exact Mass: 337.1438

Molecular Weight: 337.35

Elemental Analysis: C, 56.97; H, 5.98; F, 5.63; N, 12.46; O, 18.97

Price and Availability

Size	Price	Availability
250mg	USD 250.00	Ready to ship
500mg	USD 400.00	Ready to ship
1g	USD 600.00	Ready to ship
2g	USD 950.00	Ready to ship
5g	USD 1,550.00	Ready to ship

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Related CAS #

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Synonym

Linezolid; Zyvox; Zyvoxid; Zyvoxam; PNU 100766; PNU-100766; PNU100766; U 100766; U-100766; U100766.

IUPAC/Chemical Name

N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide

InChi Key

TYZROVQLWOKYKF-ZDUSSCGKSA-N

InChi Code

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

SMILES Code

CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCOCC3)F

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A24M03B15

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Linezolid is the first member of the class of oxazolidinone synthetic antibiotic. Linezolid acts by inhibiting the initiation of bacterial protein synthesis.

In vitro activity:

In this study, linezolid showed excellent in vitro activity against all the strains tested (MICs ≤ 1 μg/ml), including those resistant to SIRE (streptomycin, isoniazid, rifampin, and ethambutol). Reference: Antimicrob Agents Chemother. 2003 Jan;47(1):416-7. https://pubmed.ncbi.nlm.nih.gov/12499228/

In vivo activity:

Serum cytokine analyses revealed that compared to untreated and vancomycin-treated mice infected with IDRL-7971, linezolid-treated HLA-DR3 transgenic mice infected with IDRL-7971, had significantly lower levels of IL-2, IL-6, and the chemokine KC (Fig. 6). These results suggest that linezolid played a protective role by attenuating the production of SAg in vivo. Reference: Antimicrob Agents Chemother. 2012 Oct;56(10):5401-5. https://pubmed.ncbi.nlm.nih.gov/22850509/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	88.93
	DMSO	55.4	164.32
	Ethanol	5.8	17.22
	PBS (pH 7.2)	0.1	0.30

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 337.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Alcalá L, Ruiz-Serrano MJ, Pérez-Fernández Turégano C, García De Viedma D, Díaz-Infantes M, Marín-Arriaza M, Bouza E. In vitro activities of linezolid against clinical isolates of Mycobacterium tuberculosis that are susceptible or resistant to first-line antituberculous drugs. Antimicrob Agents Chemother. 2003 Jan;47(1):416-7. doi: 10.1128/AAC.47.1.416-417.2003. PMID: 12499228; PMCID: PMC148996. 2. Noskin GA, Siddiqui F, Stosor V, Hacek D, Peterson LR. In vitro activities of linezolid against important gram-positive bacterial pathogens including vancomycin-resistant enterococci. Antimicrob Agents Chemother. 1999 Aug;43(8):2059-62. doi: 10.1128/AAC.43.8.2059. PMID: 10428937; PMCID: PMC89415. 3. Jacqueline C, Broquet A, Roquilly A, Davieau M, Caillon J, Altare F, Potel G, Asehnoune K. Linezolid dampens neutrophil-mediated inflammation in methicillin-resistant Staphylococcus aureus-induced pneumonia and protects the lung of associated damages. J Infect Dis. 2014 Sep 1;210(5):814-23. doi: 10.1093/infdis/jiu145. Epub 2014 Mar 11. PMID: 24620024. 4. Karau MJ, Tilahun AY, Schmidt SM, Clark CR, Patel R, Rajagopalan G. Linezolid is superior to vancomycin in experimental pneumonia caused by Superantigen-Producing staphylococcus aureus in HLA class II transgenic mice. Antimicrob Agents Chemother. 2012 Oct;56(10):5401-5. doi: 10.1128/AAC.01080-12. Epub 2012 Jul 30. PMID: 22850509; PMCID: PMC3457354.

In vitro protocol:

In vivo protocol:

1. Jacqueline C, Broquet A, Roquilly A, Davieau M, Caillon J, Altare F, Potel G, Asehnoune K. Linezolid dampens neutrophil-mediated inflammation in methicillin-resistant Staphylococcus aureus-induced pneumonia and protects the lung of associated damages. J Infect Dis. 2014 Sep 1;210(5):814-23. doi: 10.1093/infdis/jiu145. Epub 2014 Mar 11. PMID: 24620024. 2. Karau MJ, Tilahun AY, Schmidt SM, Clark CR, Patel R, Rajagopalan G. Linezolid is superior to vancomycin in experimental pneumonia caused by Superantigen-Producing staphylococcus aureus in HLA class II transgenic mice. Antimicrob Agents Chemother. 2012 Oct;56(10):5401-5. doi: 10.1128/AAC.01080-12. Epub 2012 Jul 30. PMID: 22850509; PMCID: PMC3457354.

1: El-Naggari M, El Nour I, Al-Nabhani D, Al Muharrmi Z, Gaafar H, Abdelmogheth AA. Nocardia asteroides peritoneal dialysis-related peritonitis: First case in pediatrics, treated with protracted linezolid. J Infect Public Health. 2016 Mar-Apr;9(2):192-7. doi: 10.1016/j.jiph.2015.11.003. Epub 2016 Jan 4. PubMed PMID: 26768669. 2: Kingsley J, Mehra P, Lawrence LE, Henry E, Duffy E, Cammarata SK, Pullman J. A randomized, double-blind, Phase 2 study to evaluate subjective and objective outcomes in patients with acute bacterial skin and skin structure infections treated with delafloxacin, linezolid or vancomycin. J Antimicrob Chemother. 2016 Mar;71(3):821-9. doi: 10.1093/jac/dkv411. Epub 2015 Dec 17. PubMed PMID: 26679243; PubMed Central PMCID: PMC4743703. 3: Echeverría-Esnal D, Retamero A, Pardos SL, Grau S. Severe thrombocytopenia caused by linezolid poisoning in an underweight critically ill patient with renal impairment treated with the recommended doses. Enferm Infecc Microbiol Clin. 2016 Mar;34(3):213-4. doi: 10.1016/j.eimc.2015.06.012. Epub 2015 Jul 26. PubMed PMID: 26211841. 4: Patel K, Kabir R, Ahmad S, Allen SL. Assessing outcomes of adult oncology patients treated with linezolid versus daptomycin for bacteremia due to vancomycin-resistant Enterococcus. J Oncol Pharm Pract. 2016 Apr;22(2):212-8. doi: 10.1177/1078155214556523. Epub 2014 Oct 17. PubMed PMID: 25326010. 5: Doern CD, Park JY, Gallegos M, Alspaugh D, Burnham CA. Investigation of Linezolid Resistance in Staphylococci and Enterococci. J Clin Microbiol. 2016 Mar 2. pii: JCM.01929-15. [Epub ahead of print] PubMed PMID: 26935728. 6: Srinivas NR, Syed M. Applicability of a Single Time Point Strategy for the Prediction of Area Under the Concentration Curve of Linezolid in Patients: Superiority of C trough- over C max-Derived Linear Regression Models. Drugs R D. 2016 Mar;16(1):69-79. doi: 10.1007/s40268-015-0117-5. PubMed PMID: 26747454. 7: Balandin B, Lobo B, Orden B, Román F, García E, Martínez R, Valdivia M, Ortega A, Fernández I, Galdos P. Emergence of linezolid-resistant coagulase-negative staphylococci in an intensive care unit. Infect Dis (Lond). 2016 May;48(5):343-9. doi: 10.3109/23744235.2015.1122225. Epub 2015 Dec 15. PubMed PMID: 26670684. 8: Cafini F, Nguyen le TT, Higashide M, Román F, Prieto J, Morikawa K. Horizontal gene transmission of the cfr gene to MRSA and Enterococcus: role of Staphylococcus epidermidis as a reservoir and alternative pathway for the spread of linezolid resistance. J Antimicrob Chemother. 2016 Mar;71(3):587-92. doi: 10.1093/jac/dkv391. Epub 2015 Dec 11. PubMed PMID: 26661395. 9: Bobylev I, Maru H, Joshi AR, Lehmann HC. Toxicity to sensory neurons and Schwann cells in experimental linezolid-induced peripheral neuropathy. J Antimicrob Chemother. 2016 Mar;71(3):685-91. doi: 10.1093/jac/dkv386. Epub 2015 Nov 26. PubMed PMID: 26612872. 10: Ishiwada N, Takaya A, Kimura A, Watanabe M, Hino M, Ochiai H, Matsui M, Shibayama K, Yamamoto T. Linezolid-resistant Staphylococcus epidermidis associated with long-term, repeated linezolid use in a pediatric patient. J Infect Chemother. 2016 Mar;22(3):187-90. doi: 10.1016/j.jiac.2015.10.004. Epub 2015 Nov 19. PubMed PMID: 26603427. 11: Li H, Lu J, Liu J, Zhao Y, Ni X, Zhao S. Linezolid is Associated with Improved Early Outcomes of Childhood Tuberculous Meningitis. Pediatr Infect Dis J. 2016 Feb 17. [Epub ahead of print] PubMed PMID: 26901441. 12: Guirao-Arrabal E, León-Ruíz L, Pérez-Sola MJ, Carrillo-Alascio PL. Clarithromycin plus linezolid as a sequential therapy for implantable-cardioverter-defibrillator infection caused by coagulase-negative staphylococci. Rev Esp Quimioter. 2016 Feb 16. pii: guirao16feb2016. [Epub ahead of print] PubMed PMID: 26888341. 13: Yılmaz PÖ, Mutlu NM, Sertçelik A, Baştuğ A, Doğu C, Kışlak S. Linezolid and dexamethasone experience in a serious case of listeria rhombencephalitis. J Infect Public Health. 2016 Feb 6. pii: S1876-0341(16)00009-5. doi: 10.1016/j.jiph.2015.12.018. [Epub ahead of print] PubMed PMID: 26860968. 14: Banniettis N, Sharma R, Hand I, Peloquin CA, Kohlhoff S, Hammerschlag MR. Steady-state pharmacokinetics of oral linezolid suspension in a premature infant with osteomyelitis. J Antimicrob Chemother. 2016 Feb 6. pii: dkv507. [Epub ahead of print] PubMed PMID: 26851607. 15: Pettit NN, Alonso V, Wojcik E, Anyanwu EC, Ebara L, Benoit JL. Possible serotonin syndrome with carbidopa-levodopa and linezolid. J Clin Pharm Ther. 2016 Feb;41(1):101-3. doi: 10.1111/jcpt.12352. PubMed PMID: 26813986. 16: Yu HC, Pan CW, Xie QP, Zheng Y, Hu YZ, Lin YM. Simultaneous determination of tedizolid and linezolid in rat plasma by ultra performance liquid chromatography tandem mass spectrometry and its application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Feb 1;1011:94-8. doi: 10.1016/j.jchromb.2015.12.056. Epub 2016 Jan 2. PubMed PMID: 26773886. 17: Libershteyn Y. Ethambutol/Linezolid Toxic Optic Neuropathy. Optom Vis Sci. 2016 Feb;93(2):211-7. doi: 10.1097/OPX.0000000000000783. PubMed PMID: 26636399. 18: Mihic T, Chow I, Mabasa V. Linezolid Dosing in a Morbidly Obese Patient With MRSA Pneumonia. Ann Pharmacother. 2016 Feb;50(2):154. doi: 10.1177/1060028015620801. Epub 2015 Dec 2. PubMed PMID: 26635362. 19: Brenciani A, Morroni G, Pollini S, Tiberi E, Mingoia M, Varaldo PE, Rossolini GM, Giovanetti E. Characterization of novel conjugative multiresistance plasmids carrying cfr from linezolid-resistant Staphylococcus epidermidis clinical isolates from Italy. J Antimicrob Chemother. 2016 Feb;71(2):307-13. doi: 10.1093/jac/dkv341. Epub 2015 Oct 15. PubMed PMID: 26472766. 20: Tian J, Xu ZL, Liu DH, Huang XJ, Liu KY, Chen H, Chen YY, Chen Y, Zhang XH, Han W, Zhang YY, Wang FR, Wang Y, Yan CH, Xu LP. [A comparison of efficacy and safety of linezolid versus vancomycin for the treatment of infections in patients after allogeneic hematopoietic stem cell transplantation]. Zhonghua Nei Ke Za Zhi. 2016 Feb;55(2):97-101. doi: 10.3760/cma.j.issn.0578-1426.2016.02.006. Chinese. PubMed PMID: 26875576.