Idoxuridine

Idoxuridine
Idoxuridine - Idoxuridin.svg
Clinical data
Other namesIododeoxyuridine; IUdR
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601062
Pregnancy
category
  • B1 (topical), B3 (ophthalmologic) [AU]
Routes of
administration
topically
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Identifiers
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.189 Edit this at Wikidata
Chemical and physical data
FormulaC9H11IN2O5
Molar mass354.100 g·mol−1
3D model (JSmol)
  • InChI=1S/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7?/m0/s1 checkY
  • Key:XQFRJNBWHJMXHO-GFCOJPQKSA-N checkY
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Idoxuridine is an anti-herpesvirus antiviral drug.

It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into viral DNA replication, but the iodine atom added to the uracil component blocks base pairing. It is used only topically due to cardiotoxicity. It was synthesized by William Prusoff in the late 1950s.[1] Initially developed as an anticancer drug, idoxuridine became the first antiviral agent in 1962.[2]

  1. ^ Cite error: The named reference Prusoff was invoked but never defined (see the help page).
  2. ^ Wilhelmus KR (2015). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". Cochrane Database Syst Rev. 1: CD002898. doi:10.1002/14651858.CD002898.pub5. PMC 4443501. PMID 25879115.