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Eperezolid

CAT: 0804-HY-10393-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-10393-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Eperezolid (PNU-100592) is an orally active protein synthesis inhibitor that targets the bacterial 50S ribosomal subunit. Eperezolid competitively binds to a specific site on the ribosomal 50S subunit (overlapping with the binding sites of chloramphenicol and lincomycin (HY-117660) ) to inhibit the translation initiation stage and exert antibacterial activity. Eperezolid can induce host cell autophagy to enhance the clearance of intracellular mycobacteria, and its MIC90 for Staphylococcus aureus and Enterococcus is 1-4 μg/mL. Eperezolid is mainly used for antibacterial research on infections with Gram-positive bacteria such as methicillin-resistant (HY-121544) Staphylococci and vancomycin-resistant (HY-B0671) Enterococci, as well as infections with intracellular bacteria such as Mycobacterium tuberculosis[1][2][3][4].
CAS Number
165800-04-4
Product Name Alternative
PNU-100592
UNSPSC
12352005
Hazard Statement
H315, H319, H320
Target
Antibiotic; Bacterial
Type
Reference compound
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/Eperezolid.html
Purity
96.55
Solubility
DMSO : 40 mg/mL (ultrasonic)
Smiles
O=C(O[C@H]1CNC(C)=O)N(C1)C2=CC(F)=C(C=C2)N3CCN(CC3)C(CO)=O
Molecular Formula
C18H23FN4O5
Molecular Weight
394.40
Precautions
H315, H319, H320
References & Citations
[1]Rybak MJ, et al. Comparative in vitro activities and postantibiotic effects of the oxazolidinone compounds eperezolid (PNU-100592) and linezolid (PNU-100766) versus vancomycin against Staphylococcus aureus, coagulase-negative staphylococci, Enterococcus faecalis, and Enterococcus faecium. Antimicrob Agents Chemother. 1998 Mar;42 (3) :721-4.|[2]Nayak, et al. Eperezolid modulates autophagy to control the growth of intracellular mycobacteria. (2023) .|[3]Schülin T, et al. Activities of the oxazolidinones linezolid and eperezolid in experimental intra-abdominal abscess due to Enterococcus faecalis or vancomycin-resistant Enterococcus faecium. Antimicrob Agents Chemother. 1999 Dec;43 (12) :2873-6.|[4]Lin AH, et al. The oxazolidinone eperezolid binds to the 50S ribosomal subunit and competes with binding of chloramphenicol and lincomycin. Antimicrob Agents Chemother. 1997 Oct;41 (10) :2127-31.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 3
Isoform
Oxazolidinone

Chemical Information

Eperezolid

Eperezolid is a small molecule drug. The usage of the INN stem '-zolid' in the name indicates that Eperezolid is a oxazolidinone antibacterial. Eperezolid has a monoisotopic molecular weight of 394.17 Da.

CAS Number165800-04-4
PubChem CID73214
IUPAC NameN-[[(5S)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
Molecular FormulaC18H23FN4O5
Molecular Weight394.4
XLogP-0.3
Topological Polar Surface Area102
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Heavy Atom Count28
Formal Charge0
Complexity599
SMILES
CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCN(CC3)C(=O)CO)F
InChI
InChI=1S/C18H23FN4O5/c1-12(25)20-9-14-10-23(18(27)28-14)13-2-3-16(15(19)8-13)21-4-6-22(7-5-21)17(26)11-24/h2-3,8,14,24H,4-7,9-11H2,1H3,(H,20,25)/t14-/m0/s1
InChIKey
SIMWTRCFFSTNMG-AWEZNQCLSA-N
Chemical Structure
2D Structure
2D structure of Eperezolid
CAS: 165800-04-4
CID: 73214
Formula: C18H23FN4O5
MW: 394.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight394.4
XLogP3-0.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Exact Mass394.16524801
Monoisotopic Mass394.16524801
Topological Polar Surface Area102 Ų
Heavy Atom Count28
Formal Charge0
Complexity599
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
B3390-100Eperezolid
448286-01Eperezolid-d3
sc-498628Eperezolid-d8
A13486-500Eperezolid 500mg
A13486-50Eperezolid 50mg
A13486-1Eperezolid 1mg
A13486-100Eperezolid 100mg
A13486-5Eperezolid 5mg
A13486-2Eperezolid 2mg
A13486-25Eperezolid 25mg

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