A prodrug of the antiviral tenofovir
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Tenofovir Disoproxil (fumarate)

Item No. 16922

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]-2,4,6,8-tetraoxa-5-phosphanonanedioic acid, 1,9-bis(1-methylethyl) ester 5-oxide, (2E)-2-butenedioate
CAS Number
202138-50-9
Synonyms
  • Bis(POC)-PMPA
Molecular Formula
C19H30N5O10P • C4H4O4
Formula Weight
635.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMF:PBS (pH 7.2) (1:9): 0.1 mg/mlDMSO: 14 mg/mlEthanol: 5 mg/ml
λmax
209, 260 nm
SMILES
O=P(OCOC(OC(C)C)=O)(OCOC(OC(C)C)=O)CO[C@H](C)CN1C=NC2=C(N)N=CN=C21.O=C(O)/C=C/C(O)=O
InChi Code
InChI=1S/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1
InChi Key
VCMJCVGFSROFHV-WZGZYPNHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    Tenofovir disoproxil is a prodrug of the acyclic nucleoside phosphonate, tenofovir (Item No. 13874).1,2 Tenofovir 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 Due to its rapid intracellular uptake, the anti-HIV activity of tenofovir disoproxil is reportedly >100-fold greater than that of the negatively charged tenofovir in a T cell line and primary blood lymphocytes.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. De Clercq, E. Clinical potential of the acyclic nucleoside phosphonates cidofovir, adefovir, and tenofovir in treatment of DNA virus and retrovirus infections. Clin. Microbiol. Rev. 16(4), 569-596 (2003).

    2. 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).

    3. 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).

    4. 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).