An internal standard for the quantification of tenofovir
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Unlabeled Version(s)
13874Tenofovir
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Tenofovir-d6

Item No. 21071

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
P-[[1-[(6-amino-9H-purin-9-yl)methyl-d2]ethoxy-1,2,2,2-d4]methyl]-phosphonic acid
CAS Number
1020719-94-1
Synonyms
  • GS-1275-d6
  • GS-1278-d6
  • (R)-PMPA-d6
  • TDF-d6
Molecular Formula
C9H8D6N5O4P
Formula Weight
293.3
Purity
≥99% deuterated forms (d1-d6)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SparinglyWater: Sparingly
SMILES
OP(COC(C([2H])([2H])[2H])([2H])C([2H])([2H])N1C=NC2=C(N)N=CN=C21)(O)=O
InChi Code
InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/i1D3,2D2,6D
InChi Key
SGOIRFVFHAKUTI-CUYPRXAISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Tenofovir-d6 is intended for use as an internal standard for the quantification of tenofovir (Item No. 13874) by GC- or LC-MS. Tenofovir is an analog of adenosine monophosphate that has antiviral activity.1,2 It is converted by cellular enzymes to tenofovir diphosphate, an obligate chain terminator that inhibits the activity of HIV reverse transcriptase and hepatitis B virus polymerase.3,4 Tenofovir diphosphate is a weak inhibitor of mammalian DNA polymerases α and β and mitochondrial DNA polymerase γ.4 For in vivo and cell culture use, tenofovir is supplied as a water soluble prodrug in the form of tenofovir disoproxil (fumarate) (Item No. 16922), which increases the intracellular diphosphorylated compound >1,000-fold above the level attained with unmodified tenofovir.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Balzarini, J., Vahlenkamp, T., Egberink, H., et al. Antiretroviral activities of acyclic nucleoside phosphonates [9-(2-phosphonylmethoxyethyl)adenine, 9-(2-phosphonylmethoxyethyl)guanine, (R)-9-(2-phosphonylmethoxypropyl)adenine, and MDL 74,968] in cell cultures and murine sarcoma virus-infected newborn NMRI mice. Antimicrob. Agents Chemother. 41(3), 611-616 (1997).

    2. Balzarini, J., Holy, A., Jindrich, J., et al. Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: Potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine. Antimicrob. Agents Chemother. 37(2), 332-338 (1993).

    3. Van Gelder, J., Shafiee, M., De Clercq, E., et al. Species-dependent and site-specific intestinal metabolism of ester prodrugs. Int. J. Pharm. 205(1-2), 93-100 (2000).

    4. Robbins, B.L., Srinivas, R.V., Kim, C., et al. Anti-human immunodeficiency virus activity and cellular metabolism of a potential prodrug of the acyclic nucleoside phosphonate 9-R-(2-phosphonomethoxypropyl)adenine (PMPA), bis(isopropyloxymethylcarbonyl)PMPA. Antimicrob. Agents Chemother. 42(3), 612-617 (1998).