Oseltamivir Phosphate

- Overview
  - Oseltamivir Phosphate is an inhibitor of influenza viral neuraminidase. It is also an antiviral used against influenza A and B. Oseltamivir was discovered at Gilead in 1997 using shikimic acid as a starting point for synthesis. The compound has promising anti-cancer activity. Oseltamivir Phosphate is slightly soluble in DMSO but sparingly soluble in water.
    
    Please contact us at for specific academic pricing.
    
    Background
    
    Oseltamivir Phosphate is converted to its active form (Oseltamivir Carboxylate) in vivo by hepatic esterases via ester hydrolysis. Oseltamivir Carboxylate inhibits influenza viral neuraminidase (syn: sialidase) , an enzyme which cleaves sialic acid residues. The residues are found on glycoproteins on the cell surface of human cells that help new virions exit the cell. The result is that the newly replicated virus cannot be released from infected cells of the respiratory tract and thus cannot replicate.
- Properties
  - CAS Number
    
    204255-11-8
    
    Molecular Formula
    
    C16H28N2O4 ∙ H3PO4
    
    Molecular Weight
    
    410.40
    
    Appearance
    
    White to off-white powder
    
    Solubility
    
    Slighly soluble in DMSO. Sparingly soluble in water.
    
    Other Properties
    
    Source: Synthetic
    Purity Level: ≥98%-101.5% (anhydrous basis)
    
    Storage
    
    -20°C
    
    * For research use only
- Applications
  - Application Description
    
    Spectrum: Oseltamivir has broad-spectrum activity against a range of influenza A and B subtypes, due to the conserved nature of the neuraminidase enzyme, which is highly selective for influenza only (neuraminidase A and B). It is effective for human seasonal viruses, avian viruses, and pandemic viruses including H1N1 virus.
    
    Microbiology Applications: Oseltamivir Phosphate IC50 range for influenza A and B subtypes is ≤ 1 nM - 30 nM. Resistance to Oseltamivir is due to single amino acid residue substitutions (His274Tyr in N1) in the neuraminidase enzyme.
    
    Eukaryotic Cell Culture Applications: In a functional assay with MDCK cells, Oseltamivir Phosphate was assessed for antiinfluenza activity against influenza A virus H3N2 infected MDCK cells. Inhibition of virus-induced cytopathic effect was recorded after 36 hours; IC50=1.1 µM.
    
    Cancer Applications: The antitumor activity of Oseltamivir Phosphate was studied in a mouse model with human triple-negative breast adenocarcinoma using MCF-7 and MDA-MB-231 cell lines. The compound was able to completely ablate tumor vascularization, tumor growth, and metastasis when used at 50 mg/kg (Haxho et al, 2014).
    The anti-cancer properties of Oseltamivir Phosphate was studied in human pancreatic cancer (PANC1) cells with acquired resistance to cisplatin and gemcitabine. Authors found it was efficacious in overcoming the intrinsic resistance of the cell to chemotherapeutics and metastasis. Targeting the Neu 1 sialidase enzyme with Oseltamivir Phosphate at the growth factor receptor level disables the signaling platform for cancer cells. It was able to reverse epithelial-mesenchymal transition (EMT), as demonstrated by the expression of N-cadherin, VE-cadherin and E-cadherin as characteristic markers of EMT, which is the suggested mechanism by which cancer cells acquire resistance to chemotherapy (O’Shea et al, 2014).