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165800-03-3 molecular structure
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N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

ChemBase ID: 483
Molecular Formular: C16H20FN3O4
Molecular Mass: 337.3461032
Monoisotopic Mass: 337.14378436
SMILES and InChIs

SMILES:
Fc1c(N2CCOCC2)ccc(N2C[C@@H](OC2=O)CNC(=O)C)c1
Canonical SMILES:
CC(=O)NC[C@@H]1OC(=O)N(C1)c1ccc(c(c1)F)N1CCOCC1
InChI:
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
InChIKey:
TYZROVQLWOKYKF-ZDUSSCGKSA-N

Cite this record

CBID:483 http://www.chembase.cn/molecule-483.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
IUPAC Traditional name
linezolid
Brand Name
Linezlid
Zyvox
Zyvoxid
Synonyms
linezolid
Linezolid
N-{[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide
Linospan
Linox
PNU 100766
U 100766
(S)-N-((3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
Zyvox
PNU-100766
U-100766
Zyvoxid
Zyvoxam
N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
Linezolid
CAS Number
165800-03-3
MDL Number
MFCD00937825
PubChem SID
160963946
46504452
PubChem CID
441401

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.453722  H Acceptors
H Donor LogD (pH = 5.5) 0.63666356 
LogD (pH = 7.4) 0.6366636  Log P 0.6366637 
Molar Refractivity 84.4748 cm3 Polarizability 32.025 Å3
Polar Surface Area 71.11 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.61  LOG S -2.37 
Solubility (Water) 1.44e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
3 mg/mL expand Show data source
Chloroform expand Show data source
DMSO: >20 mg/mL expand Show data source
Apperance
White Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
176-178°C expand Show data source
Hydrophobicity(logP)
0.9 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
RTECS
AC2720000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H372 expand Show data source
GHS Precautionary statements
P314 expand Show data source
Storage Temperature
room temp expand Show data source
Target Organ
Bone expand Show data source
Purity
≥98% (HPLC) expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C16H20FN3O4 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00601 external link
Item Information
Drug Groups approved; investigational
Description Linezolid is a synthetic antibiotic, the first of the oxazolidinone class, used for the treatment of infections caused by multi-resistant bacteria including streptococcus and methicillin-resistant Staphylococcus aureus (MRSA). The drug works by inhibiting the initiation of bacterial protein synthesis.
Indication For the treatment of bacterial infections caused by susceptible strains of vancomycin resistant Enterococcus faecium, Staphylococcal aureus (methicillin resistant and susceptible strains), Streptococcus pneumoniae, Streptococcus pyogenes, Streptococcus agalactiae.
Pharmacology Linezolid is a synthetic antibacterial agent of a new class of antibiotics, the oxazolidinones, which has clinical utility in the treatment of infections caused by aerobic Gram-positive bacteria. The in vitro spectrum of activity of linezolid also includes certain Gram-negative bacteria and anaerobic bacteria. Susceptible organisms include methicillin- and vancomycin-resistant staphylococci, vancomycin-resistant enterococci, penicillin-resistant pneumococci and anaerobes. Oxazolidinones inhibit protein synthesis by binding at the P site at the ribosomal 50S subunit. Resistance to other protein synthesis inhibitors does not affect oxazolidinone activity, however rare development of oxazolidinone resistance cases, associated with 23S rRNA alterations during treatment have been reported. Linezolid inhibits bacterial protein synthesis through a mechanism of action different from that of other antibacterial agents; therefore, cross-resistance between linezolid and other classes of antibiotics is unlikely.
Toxicity Clinical signs of acute toxicity lead to decreased activity, ataxia, vomiting and tremors.
Affected Organisms
Gram negative and gram positive bacteria
Biotransformation Linezolid is primarily metabolized by oxidation of the morpholine ring, which results in two inactive ring-opened carboxylic acid metabolites: the aminoethoxyacetic acid metabolite (A), and the hydroxyethyl glycine metabolite
Absorption Linezolid is rapidly and extensively absorbed after oral dosing. Maximum plasma concentrations are reached approximately 1 to 2 hours after dosing, and the absolute bioavailability is approximately 100%.
Half Life 4.5-5.5 hours
Protein Binding 31%
Distribution * 40 to 50 L [healthy adult volunteers]
References
[Link]
Park IN, Hong SB, Oh YM, Kim MN, Lim CM, Lee SD, Koh Y, Kim WS, Kim DS, Kim WD, Shim TS: Efficacy and tolerability of daily-half dose linezolid in patients with intractable multidrug-resistant tuberculosis. J Antimicrob Chemother. 2006 Sep;58(3):701-4. Epub 2006 Jul 19. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
DrugBank - DB08769 external link
Drug information: experimental
Selleck Chemicals - S1408 external link
Research Area: Infection
Biological Activity:
Linezolid (Zyvox) is a synthetic antibiotic used for the treatment of serious infections caused by Gram-positive bacteria that are resistant to several other antibiotics. A member of the oxazolidinone class of drugs, linezolid is active against most Gram-positive bacteria that cause disease, including streptococci, vancomycin-resistant enterococci (VRE), and methicillin-resistant Staphylococcus aureus (MRSA). [1]
Sigma Aldrich - PZ0014 external link
Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Linezolid is an oxazolidinone antimicrobial. It binds to a site on the bacterial 23S ribosomal RNA of the 50S subunit and prevents the formation of a functional 70S initiation complex, thus inhibiting bacterial mRNA translation. Linezolid is also a weak, reversible, nonselective inhibitor of monoamine oxidase.
Toronto Research Chemicals - L466500 external link
Prototype of the oxazolidinone antimicrobials; inhibits bacterial mRNA translation.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  Link
  • • Park IN, Hong SB, Oh YM, Kim MN, Lim CM, Lee SD, Koh Y, Kim WS, Kim DS, Kim WD, Shim TS: Efficacy and tolerability of daily-half dose linezolid in patients with intractable multidrug-resistant tuberculosis. J Antimicrob Chemother. 2006 Sep;58(3):701-4. Epub 2006 Jul 19. Pubmed
  • • http://en.wikipedia.org/wiki/Linezolid
  • • Brickner, S.J., et al.: J. Med. Chem., 39, 673 (1996)
  • • Ford, C.W., et al.: Antimicrob. Agents Chemother., 40, 1508 (1996)
  • • Rybak, M.J., et al.: Pharmacotherapy, 18, 456 (1996)
  • • Stevens, D.L., et al.: Clin. Infect. Dis., 34, 1481 (1996)
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PATENTS

PATENTS

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