Edoxudine

Edoxudine

Systematic (IUPAC) name
5-ethyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Identifiers
CAS Number	15176-29-1 Y
ATC code	D06BB09 (WHO)
PubChem	CID: 66377
ChemSpider	59752 N
UNII	15ZQM81Y3R Y
ChEMBL	CHEMBL318153 N
Chemical data
Formula	C11H16N2O5
Molecular mass	256.25514
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 N Key:XACKNLSZYYIACO-DJLDLDEBSA-N N
NY (what is this?)  (verify)

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

It has shown effectiveness against herpes simplex virus.

Synthesis

Edoxudine synthesis: Synthesis via organopalladium intermediates:

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.