A potential impurity found in commercial emtricitabine preparations
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Emtricitabine S-oxide

Item No. 26654

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-3-oxido-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
CAS Number
152128-77-3
Molecular Formula
C8H10FN3O4S
Formula Weight
263.2
Purity
≥98% (mixture of diastereomers)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: heated, slightly
SMILES
O=C1N([C@H]2O[C@@H](CO)S(C2)=O)C=C(F)C(N)=N1
InChi Code
InChI=1S/C8H10FN3O4S/c9-4-1-12(8(14)11-7(4)10)5-3-17(15)6(2-13)16-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+,17?/m0/s1
InChi Key
DMOMZPWPIDCLMB-YGFFCSEESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Emtricitabine S-oxide is a potential impurity found in commercial preparations of emtricitabine.1 Emtricitabine (Item No. 16879) is a nucleoside analog and an inhibitor of HIV-1 and hepatitis B reverse transcriptase with antiviral activity.2 It inhibits replication of HIV-1 (EC50s = 10-20 nM) and hepatitis B (EC50s = 10-40 nM) in various cell lines.3 Emtricitabine inhibits duck hepatitis B viral DNA synthesis when administered pre- and post-viral inoculation in primary duck hepatocytes.4 In vivo, emtricitabine (3-30 mg/kg) reduces viremia and hepatic woodchuck hepatitis virus (WHV) replication in a dose-dependent manner in a woodchuck model of chronic WHV infection.5 Formulations containing emtricitabine have been used in the treatment of HIV infection.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mali, A., and More, U. RP-HPLC method for simultaneous estimation of impurities from emtricitabine and tenofovir disoproxil fumarate tablet. Int. J. Pharm. Sci. Res. 7(4), 1662-1669 (2016).

    2. Nelson, M., and Schiavone, M. Emtricitabine (FTC) for the treatment of HIV infection. Int. J. Clin. Pract. 58(5), 504-510 (2004).

    3. Darque, A., Valette, G., Rousseau, F., et al. Quantitation of intracellular triphosphate of emtricitabine in peripheral blood mononuclear cells from human immunodeficiency virus-infected patients. Antimicrob. Agents Chemother. 43(9), 2245-2250 (1999).

    4. Seignères, B., Martin, P., Werle, B., et al. Effects of pyrimidine and purine analog combinations in the duck hepatitis B virus infection model. Antimicrob. Agents Chemother. 47(6), 1842-1852 (2003).

    5. Korba, B.E., Schinazi, R.F., Cote, P., et al. Effect of oral administration of emtricitabine on woodchuck hepatitis virus replication in chronically infected woodchucks. Antimicrob. Agents Chemother. 44(6), 1757-1760 (2000).