The prodrug of a neuraminidase inhibitor
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Active Metabolite(s)
15779Oseltamivir Acid
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Oseltamivir (phosphate)

Item No. 16070

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4R-(acetylamino)-5S-amino-3R-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid, ethyl ester, monophosphate
CAS Number
204255-11-8
Synonyms
  • GS-4104
  • Ro 64-0796/002
Molecular Formula
C16H28N2O4 • H3PO4
Formula Weight
410.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.5 mg/mlDMSO: 10 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
N[C@@H]1[C@@H](NC(C)=O)[C@H](OC(CC)CC)C=C(C(OCC)=O)C1.O=P(O)(O)O
InChi Code
InChI=1S/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19;1-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19);(H3,1,2,3,4)/t13-,14+,15+;/m0./s1
InChi Key
PGZUMBJQJWIWGJ-ONAKXNSWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Oseltamivir is an antiviral prodrug targeted against the influenza viruses.1,2 Once hydrolyzed in the liver to its active metabolite, oseltamivir acid (Item No. 15779), it can competitively inhibit viral neuraminidase (IC50s = 0.1-4.9 nM for influenza neuraminidases A and B), blocking the release of new viral particles from a host cell.3,4,5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sidwell, R.W., Huffman, J.H., Barnard, D.L., et al. Inhibition of influenza virus infections in mice by GS4104, an orally effective influenza virus neuraminidase inhibitor. Antiviral Res. 37(2), 107-120 (1998).

    2. Hayden, F.G., Atmar, R.L., Schilling, M., et al. Use of the selective oral neuraminidase inhibitor oseltamivir to prevent influenza. N. Engl. J. Med. 341(18), 1336-1343 (1999).

    3. Li, W., Escarpe, P.S., Eisenberg, E.J., et al. Identification of GS 4104 as an orally bioavailable prodrug of the influenza virus neuraminidase inhibitor GS 4071. Antimicrob. Agents Chemother. 42(3), 647-653 (1998).

    4. Oliyai, R., Yuan, L.C., Dahl, T.C., et al. Biexponential decomposition of a neuraminidase inhibitor prodrug (GS-4104) in aqueous solution. Pharm. Res. 15(8), 1300-1304 (1998).

    5. Govorkova, E.A., Ilyushina, N.A., McClaren, J.L., et al. Susceptibility of highly pathogenic H5N1 influenza viruses to the neuraminidase inhibitor oseltamivir differs in vitro and in a mouse model. Antimicrob. Agents Chemother. 53(7), 3088-3096 (2009).

    6. Krueger, A.C., Xu, Y., Kati, W.M., et al. Synthesis of potent pyrrolidine influenza neuraminidase inhibitors. Bioorg. Med. Chem. Lett. 18(5), 1692-1695 (2008).

    7. Lew, W., Wu, H., Chen, X., et al. Carbocyclic influenza neuraminidase inhibitors possessing a C3-cyclic amine side chain: Synthesis and inhibitory activity. Bioorg. Med. Chem. Lett. 10(11), 1257-1260 (2000).