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Home> Encyclopedia >   /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Pharmaceuticals and Biochemicals
Linezolid structure
Linezolid structure


Iupac Name:N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
CAS No.: 165800-03-3
Molecular Weight:337.351
Modify Date.: 2022-11-10 21:36
Introduction: fully synthetic oxazolidinone antibiotics. oxazolidinone antibacterial drugs. anti-inflammatory drug. inhibit bacterial mRNA translation. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(S)-Linezolid Acetamide, N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- Acetamide, N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-, (S)- Acetamide,N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-, (S)- Averozolid Linospan Linox Lizoforce Lizolid N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide PNU 100766 U 100766 Zyrox Zyvox Zyvoxid

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C16H20FN3O4 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
3.1 Density
3.1 Melting point
3.1 Boiling point
585.5 oC at 760 mmHg
3.1 Refractive index
3.1 Flash Point
307.9 oC
3.1 Precise Quality
3.1 PSA
3.1 logP
3.1 Solubility
DMSO: >20mg/mL
3.2 Λmax
3.3 AnalyticLaboratory Methods
Analyte: linezolid;; matrix: blood (plasma), urine; procedure: high-performance liquid chromatography with ultraviolet detection at 251 nm; limit of quantitation: 10 ng/mL
3.4 Appearance
White Solid
3.5 Storage
Store at RT
3.6 Chemical Properties
White Solid
3.7 Color/Form
White crystals from ethyl acetate and hexanes
3.8 Physical
3.9 pKa
3.10 Water Solubility
3.11 Spectral Properties
Specific optical rotation at 20 deg C for D (sodium) line = -9 deg (c = 0.919 in chloroform)
3.12 StorageTemp
Store in original container in a cool dark place.
3. Use and Manufacturing
4.1 Definition
ChEBI: An organofluorine compound that consists of 1,3-oxazolidin-2-one bearing an N-3-fluoro-4-(morpholin-4-yl)phenyl group as well as an acetamidomethyl group at position 5. A synthetic antibacterial agent that inhibits bacterial protein syntesis by binding to a site on 23S ribosomal RNA of the 50S subunit and prevents further formation of a functional 70S initiation complex.
4.2 General Description
Linezolid (Zyvox) is an oxazolidinedione-type antibacterialagent that inhibits bacterial protein synthesis. It acts in theearly translation stage, preventing the formation of a functionalinitiation complex. Linezolid binds to the 30S and 70Sribosomal subunits and prevents initiation complexes involvingthese subunits. Collective data suggest that the oxazolidindionespartition their ribosomal interaction between thetwo subunits. Formation of the early tRNAfMet-mRNA-70Sor 30S is prevented. Linezolid is a newer synthetic agent, andhence, cross-resistance between the antibacterial agent andother inhibitors of bacterial protein synthesis has notbeen seen.Linezolid possesses a wide spectrum of activity againstGram-positive organisms, including MRSA, penicillin-resistantpneumococci, and vancomycin-resistant Enterococcusfaecalis and E. faecium. Anaerobes such as Clostridium,Peptostreptococcus, and Prevotella spp. are sensitive tolinezolid.Linezolid is a bacteriostatic agent against most susceptibleorganisms but displays bactericidal activity against somestrains of pneumococci, B. fragilis, and Clostridiumperfringens.The indications for linezolid are for complicated anduncomplicated skin and soft-tissue infections, communityandhospital-acquired pneumonia, and drug-resistant Grampositiveinfections.
4.3 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 34 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H372 (70.59%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]
H373 (14.71%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P264, P270, P314, and P501
4.4 Usage
fully synthetic oxazolidinone antibiotics. oxazolidinone antibacterial drugs. anti-inflammatory drug. inhibit bacterial mRNA translation.
4. Safety and Handling
5.1 Hazard Codes
5.1 Risk Statements
5.1 Safety Statements
5.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl linezolide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
5.2 Octanol/Water Partition Coefficient
log Kow = 1.26 (est)
5.3 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5.4 Formulations/Preparations
Parenteral: Injection, for IV infusion: 2 mg/mL (200 and 600 mg) in sterile isotonic solution Zyvox Injection ( in flexible containers), (Pfizer).
Oral: For suspension: 100 mg/5 mL Zyvox, (Pfizer); Tablets, film-coated: 600 mg Zyvox, (Pfizer).
5.5 WGK Germany
5.5 Safety

Safety Information of Acetamide,N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- (CAS NO.165800-03-3):
Hazard Codes:?HarmfulXn
Risk Statements: 20/21/22?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36?
S36:Wear suitable protective clothing.

5.6 Specification

? Acetamide,N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- (CAS NO.165800-03-3), its Synonyms are Linezolid ; N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide ; Zivoxid ; Zyvox ; Acetamide, N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-, (S)- .


2.Hazard identification

2.1 Classification of the substance or mixture

Specific target organ toxicity \u2013 repeated exposure, Category 1

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H372 Causes damage to organs through prolonged or repeated exposure

Precautionary statement(s)

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.


P314 Get medical advice/attention if you feel unwell.




P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


8. Other Information
8.0 Outline
Linezolid (U-100766, PNU-100766) developed and produced by the US Pharmacia & Upiohn company (which has been acquired by Pfizer) ,is a new type of azole oxazolidinone class of synthetic antibacterial drugs, the FDA on April 18, 2000 approved the drug to market. This product is the first drug in American in 40 years which is approved for the treatment of methicillin-resistant Staphylococcus aureus infection, September 2007 month in China's listed, it belongs to the Medicare B drugs.
8.1 Indications
For the treatment of Gram-positive (G +) bacteria caused infections, including concurrent bacteremia; nosocomial pneumonia; community-acquired pneumonia ( because bacteria are not the same,pneumonia is clinically divided into hospital-acquired pneumonia and community-acquired pneumonia) and concomitant bacteremia; it can be applied for the complexity of the skin and skin and soft tissue infections, including osteomyelitis in diabetic foot infections; uncomplicated skin and skin and soft tissue infections; it is also used for the treatment of vancomycin-resistant feces enterococci.
8.2 Uses
fully synthetic oxazolidinone antibiotics.
oxazolidinone antibacterial drugs.
anti-inflammatory drug.
inhibit bacterial mRNA translation.
8.3 Chemical Properties
White Solid
8.4 Uses
Prototype of the oxazolidinone antimicrobials; inhibits bacterial mRNA translation.
8.5 Uses
8.6 Definition
ChEBI: An organofluorine compound that consists of 1,3-oxazolidin-2-one bearing an N-3-fluoro-4-(morpholin-4-yl)phenyl group as well as an acetamidomethyl group at position 5. A synthetic antibacterial agent that inhibits bacterial protein synt esis by binding to a site on 23S ribosomal RNA of the 50S subunit and prevents further formation of a functional 70S initiation complex.
8.7 Brand name
Zyvox (Pharmacia & Upjohn).
8.8 Acquired resistance
Isolates of Staph. aureus and E. faecalis for which the MIC of linezolid is raised have been obtained following serial exposure to gradients of the drug. However, induction of resistance requires many passages over several weeks. Resistance in these laboratory mutants is associated with modifications of the 23S rRNA gene.
Overall, resistance rates in clinical isolates are very low at <0.5%. Resistance is reported primarily in coagulase-negative staphylococci (1.77%) and enterococci (1.13%; mostly E. faecium), with exceptionally low resistance rates in Staph. aureus (0.06%). Risk factors for emergence of resistance include prolonged use of the drug, the presence of irremovable indwelling devices, sequestered sites of infection and low-dose therapy for infections caused by vancomycin-resistant enterococci or methicillin-resistant Staph. aureus. Resistance in clinical isolates is most often associated with gene mutations in which guanosine is replaced by uracil in the 23S rRNA. Nosocomial clonal spread of such mutants has been described in coagulase-negative staphylococci and enterococci. Resistance conferred by a novel mobile element, cfr, has been described in two isolates of staphylococci.
8.9 Pharmaceutical Applications
A synthetic oxazolidinone available for oral or intravenous administration. Soluble in water at a pH range of 5–9. Aqueous solutions (2 g/L) are stable at 25°C, 4°C and ?20°C for at least 3 months.
8.10 Biological Activity
Oxazolidinone antibiotic. Inhibits bacterial protein synthesis prior to chain initiation. Displays potent antibacterial activity against a variety of multidrug-resistant gram-positive microbes in vitro and in vivo .
8.11 Clinical Use
Linezolid is primarily used for the treatment of infections caused, or likely to be caused, by methicillin-resistant Staph. aureus, vancomycin-resistant enterococci and penicillin resistant Str. pneumoniae. Combination therapy with an antimicrobial active against Gram-negative bacteria is indicated if concomitant infection with a Gram-negative pathogen is suspected or confirmed.
Outside of licensed indications, it has been used in the treatment of bone and joint infections, endocarditis, central nervous system infections, infections in neutropenic patients and drug-resistant tuberculosis.
8.12 Side effects
Most reported adverse events are mild or moderate, with reactions severe enough to lead to withdrawal of therapy occurring in less than 3% of patients.The most frequent side effects are gastrointestinal disturbances (diarrhea, nausea, vomiting and taste alteration) and headache. The reported incidence of Clostridium difficile complications is 0.2%.
Mild and transient abnormalities of liver function tests (elevation of transaminases and/or alkaline phosphatase) occur in more than 1% of patients. Skin reactions, including rashes, dermatitis, pruritus and diaphoresis, are uncommon.
Serious but infrequent adverse drug effects include myelosuppression, peripheral neuropathy, optic neuropathy and lactic acidosis. These adverse events, which probably result from inhibition of mitochondrial protein synthesis, occur primarily in patients treated for >28 days. Myelosuppression generally occurs only after more than 2 weeks of treatment and increases with longer durations. It occurs more frequently in patients with severe renal insufficiency and is reversible on discontinuation of therapy.
Reversal of cytopenias by concomitant administration of vitamin B6 has been described. Weekly monitoring of full blood count is recommended for all patients, with more frequent monitoring of those in the following categories: pre-existing anemia or thrombocytopenia; receiving concomitant drugs that may cause anemia or thrombocytopenia; severe renal insufficiency; treatment for more than 10–14 days.
Peripheral and optic neuropathy are serious but infrequent. Most cases are associated with treatment for more than 28 days (median 5 months), but neuropathies have occurred with shorter courses. In most cases optic neuropathy improved or resolved on cessation of therapy but peripheral neuropathy did not.
Lactic acidosis can occur within a week of commencing therapy but is most often seen in patients receiving prolonged treatment (median 6 weeks).
Linezolid is a weak, reversible monoamine oxidase inhibitor (MAOI) with potential interaction with adrenergic and serotonergic drugs. Co-administration of sympathomimetics, vasopressors or dopaminergic agents may lead to an enhanced pressor response. It should be co-administered with these drugs only under conditions where close observation and monitoring of blood pressure is available, and their initial doses should be reduced and then titrated to achieve the desired pressor effect. Similarly, concomitant administration of linezolid with agents that increase central nervous system serotonin concentrations can lead to serotonin toxicity (serotonin syndrome). This most commonly follows concurrent administration of selective serotonin receptor inhibitors, but can occur with tricyclic antidepressants or any MAOI. Since MAOIs and their active metabolites have long elimination half-lives, linezolid is contraindicated in patients who are taking these drugs or have taken them in the previous 2 weeks.
9. Computational chemical data
  • Molecular Weight: 337.351g/mol
  • Molecular Formula: C16H20FN3O4
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.7
  • Exact Mass: 337.14378429
  • Monoisotopic Mass: 337.14378429
  • Complexity: 472
  • Rotatable Bond Count: 4
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Topological Polar Surface Area: 71.1
  • Heavy Atom Count: 24
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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