Edoxudine

Edoxudine (or edoxudin) is an antiviral drug. It is an analog of thymidine, a nucleoside.

Edoxudine
Clinical data
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.035.645
Chemical and physical data
FormulaC11H16N2O5
Molar mass256.25514 g·mol−1
3D model (JSmol)
 NY (what is this?)  (verify)

It has shown effectiveness against herpes simplex virus.[1]

Synthesis

Edoxudine synthesis:[2] Synthesis via organopalladium intermediates:[3][4]

Mercuration of the 2'-deoxyuridine 1 leads to the organometallic derivative 2; reaction of that with ethylene in the presence dilithiopalladium tetrachloride gives the alkylation product 3; this is reduced catalytically in situ. There is thus obtained the antiviral agent edoxudine 4.

References

  1. Hamuy R, Berman B (December 1998). "Topical antiviral agents for herpes simplex virus infections". Drugs of Today. 34 (12): 1013–25. doi:10.1358/dot.1998.34.12.487486. PMID 14743269.
  2. US 3553192, Gauri KK, issued 1971, assigned to Robugen
  3. Bergstrom DE, Ruth JL (March 1976). "Letter: Synthesis of C-5 substituted pyrimidine nucleosides via organopalladium intermediates". Journal of the American Chemical Society. 98 (6): 1587–9. doi:10.1021/ja00422a056. PMID 1249369.
  4. Bergstrom DE, Ogawa MK (1978). "C-5 substituted pyrimidine nucleosides. 2. Synthesis via olefin coupling to organopalladium intermediates derived from uridine and 2'-deoxyuridine". Journal of the American Chemical Society. 100 (26): 8106–8112. doi:10.1021/ja00494a014.
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