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Chemical Compound Review

HPMPA     [(2S)-1-(6-aminopurin-9-yl)- 3-hydroxy...

Synonyms: CHEMBL286534, GS57, SureCN385752, AG-K-93207, KST-1A9254, ...
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Disease relevance of N-(2-Phosphonomethoxyethyladenine)


High impact information on N-(2-Phosphonomethoxyethyladenine)

  • The diphosphoryl derivative (S)-HPMPApp, but not (S)-HPMPA, inhibited the DNA replication of origin containing fragments strongly [4].
  • In conclusion, we show that inside the liver, (S)-HPMPA is mainly taken up by parenchymal liver cells [5].
  • To establish effective therapeutic protocols for (S)-HPMPA, it is essential that the kinetics of its hepatic uptake be evaluated and that the role of the various liver cell types be examined [5].
  • An approach in which (S)-HPMPA is coupled to carriers that are specifically taken up by parenchymal cells may increase the effectiveness of the drug in the liver and reduce its renal toxicity [5].
  • RESULTS: Severe lowering of IOP with structural alterations of the ciliary body was observed when doses were administered that achieved final intravitreal concentrations greater than 25 microg/ml HPMPC, 200 microg/ml cyclic HPMPC (cHPMPC), 25 microg/ml (S)-HPMPA, and 625 microg/ml PMEG [6].

Chemical compound and disease context of N-(2-Phosphonomethoxyethyladenine)


Biological context of N-(2-Phosphonomethoxyethyladenine)


Anatomical context of N-(2-Phosphonomethoxyethyladenine)


Associations of N-(2-Phosphonomethoxyethyladenine) with other chemical compounds

  • The acyclic adenosine analogue (S)-9-(-3-hydroxy-2-phosphonylmethoxypropyl)adenine ((S)-HPMPA) expressed antitrypanosomal activity in vitro and vivo [11].
  • We tested several new antivirals in vitro, and found that (S)-HPMPC, (S)-HPMPA, and 2'-nor-cyclic GMP demonstrated significant serotype-dependent inhibitory activity by plaque reduction assay (ID50 = 0.017-17.0 micrograms/ml) against common clinical ocular isolates and standard adenoviral serotypes (Ad 1, Ad 5, Ad 8, and Ad 19) [14].
  • (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine [(S)-HPMPA]: a purine analogue with trypanocidal activity in vitro and in vivo [15].

Gene context of N-(2-Phosphonomethoxyethyladenine)


Analytical, diagnostic and therapeutic context of N-(2-Phosphonomethoxyethyladenine)


  1. 5-Phosphoribosyl 1-pyrophosphate synthetase converts the acyclic nucleoside phosphonates 9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine and 9-(2-phosphonylmethoxyethyl)adenine directly to their antivirally active diphosphate derivatives. Balzarini, J., De Clercq, E. J. Biol. Chem. (1991) [Pubmed]
  2. Synthesis and antiviral evaluation of alkoxyalkyl derivatives of 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)adenine against cytomegalovirus and orthopoxviruses. Beadle, J.R., Wan, W.B., Ciesla, S.L., Keith, K.A., Hartline, C., Kern, E.R., Hostetler, K.Y. J. Med. Chem. (2006) [Pubmed]
  3. Efficacy of phosphonylmethoxyalkyl derivatives of adenine in experimental herpes simplex virus and vaccinia virus infections in vivo. De Clercq, E., Holý, A., Rosenberg, I. Antimicrob. Agents Chemother. (1989) [Pubmed]
  4. Mechanism of inhibition of adenovirus DNA replication by the acyclic nucleoside triphosphate analogue (S)-HPMPApp: influence of the adenovirus DNA binding protein. Mul, Y.M., van Miltenburg, R.T., De Clercq, E., van der Vliet, P.C. Nucleic Acids Res. (1989) [Pubmed]
  5. Disposition of the acyclic nucleoside phosphonate (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine. Bijsterbosch, M.K., Smeijsters, L.J., van Berkel, T.J. Antimicrob. Agents Chemother. (1998) [Pubmed]
  6. Influence of intravitreal injections of HPMPC and related nucleoside analogues on intraocular pressure in guinea pig eyes. Banker, A.S., De Clercq, E., Taskintuna, I., Keefe, K.S., Bergeron-Lynn, G., Freeman, W.R. Invest. Ophthalmol. Vis. Sci. (1998) [Pubmed]
  7. Antimalarial and toxic effects of the acyclic nucleoside phosphonate (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine in Plasmodium berghei-infected mice. Smeijsters, L.J., Nieuwenhuijs, H., Hermsen, R.C., Dorrestein, G.M., Franssen, F.F., Overdulve, J.P. Antimicrob. Agents Chemother. (1996) [Pubmed]
  8. Efficacy of (S)-HPMPA against thymidine kinase-deficient herpes simplex virus-keratitis. Maudgal, P.C., De Clercq, E., Huyghe, P. Invest. Ophthalmol. Vis. Sci. (1987) [Pubmed]
  9. Antiviral activity of phosphonylmethoxyalkyl derivatives of purine and pyrimidines. De Clercq, E., Sakuma, T., Baba, M., Pauwels, R., Balzarini, J., Rosenberg, I., Holý, A. Antiviral Res. (1987) [Pubmed]
  10. Novel acyclic adenosine analogs inhibit Epstein-Barr virus replication. Lin, J.C., DeClercq, E., Pagano, J.S. Antimicrob. Agents Chemother. (1987) [Pubmed]
  11. Arrest of Trypanosoma brucei rhodesiense and T. brucei brucei in the S-phase of the cell cycle by (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine ((S)-HPMPA). Kaminsky, R., Nickel, B., Holý, A. Mol. Biochem. Parasitol. (1998) [Pubmed]
  12. In vitro activity of (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine against newly isolated clinical varicella-zoster virus strains. Baba, M., Konno, K., Shigeta, S., De Clercq, E. Eur. J. Clin. Microbiol. (1987) [Pubmed]
  13. Phosphonylmethoxyalkylpurines and -pyrimidines as inhibitors of African swine fever virus replication in vitro. Gil-Fernández, C., García-Villalón, D., De Clercq, E., Rosenberg, I., Holý, A. Antiviral Res. (1987) [Pubmed]
  14. Inhibitory effect of (S)-HPMPC, (S)-HPMPA, and 2'-nor-cyclic GMP on clinical ocular adenoviral isolates is serotype-dependent in vitro. Gordon, Y.J., Romanowski, E., Araullo-Cruz, T., Seaberg, L., Erzurum, S., Tolman, R., De Clercq, E. Antiviral Res. (1991) [Pubmed]
  15. (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine [(S)-HPMPA]: a purine analogue with trypanocidal activity in vitro and in vivo. Kaminsky, R., Schmid, C., Grether, Y., Holý, A., DeClercq, E., Naesens, L., Brun, R. Trop. Med. Int. Health (1996) [Pubmed]
  16. Comparative efficacy of broad-spectrum antiviral agents as inhibitors of African swine fever virus replication in vitro. Gil-Fernández, C., De Clercq, E. Antiviral Res. (1987) [Pubmed]
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