Edoxudine

Edoxudine
Clinical data
ATC code	D06BB09 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 5-ethyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;
CAS Number	15176-29-1 ;
PubChem CID	66377;
ChemSpider	59752 ;
UNII	15ZQM81Y3R;
ChEMBL	ChEMBL318153 ;
CompTox Dashboard (EPA)	DTXSID4045890 ;
ECHA InfoCard	100.035.645
Chemical and physical data
Formula	C11H16N2O5
Molar mass	256.25514 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C/1NC(=O)N(\C=C\1CC)[C@@H]2O[C@@H]([C@@H](O)C2)CO;
	InChI InChI=1S/C11H16N2O5/c1-2-6-4-13(11(17)12-10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,2-3,5H2,1H3,(H,12,16,17)/t7-,8+,9+/m0/s1 ; Key:XACKNLSZYYIACO-DJLDLDEBSA-N ;
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Edoxudine (or edoxudin) is an antiviral drug. It is an analog of thymidine, a nucleoside.

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

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.
US 3553192, Gauri KK, issued 1971, assigned to Robugen
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.
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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[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.

[BergstromOgawa1978-4] 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.