Idoxuridine

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Idoxuridine
Idoxuridine - Idoxuridin.svg
Systematic (IUPAC) name
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601062
Pregnancy cat. C (US) B1 (topical), B3 (ophthalmologic) [AU]
Legal status Prescription Only (S4) (AU)
Routes topically
Identifiers
CAS number 54-42-2 YesY
ATC code D06BB01 J05AB02, S01AD01
PubChem CID 5905
DrugBank DB00249
ChemSpider 10481938 YesY
UNII LGP81V5245 YesY
KEGG D00342 YesY
ChEMBL CHEMBL788 N
NIAID ChemDB 001857
Synonyms Iododeoxyuridine; IUdR
Chemical data
Formula C9H11IN2O5 
Mol. mass 354.099 g/mol
 N (what is this?)  (verify)

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]

Clinical use[edit]

Idoxuridine is mainly used topically to treat herpes simplex keratitis.[3] Epithelial lesions, especially initial attacks presenting with a dendritic ulcer, are most responsive to therapy, while infection with stromal involvement are less responsive.[4] Idoxuridine is ineffective against herpes simplex virus type 2 and varicella-zoster.[3]

Side effects[edit]

Common side effects of the eye drops include irritation, blurred vision and photophobia.[5] Corneal clouding and damage of the corneal epithelium may also occur.[citation needed]

Formulations and dosage[edit]

Idoxuridine is available as either a 0.5% ophthalmic ointment or as a 0.1% ophthalmic solution.[3] The dosage of the ointment is every 4 hours during day and once before bedtime.[3] The dosage of the solution is 1 drop in the conjunctival sac hourly during the day and every 2 hours during the night until definitive improvement, then 1 drop every 2 hours during the day and every 4 hours during the night.[3] Therapy is continued for 3-4 days after healing is complete, as demonstrated by fluorescein staining.[3]

See also[edit]

References[edit]

  1. ^ Prusoff, W.H. (1959) Synthesis and biological activities of iododeoxyuridine, an analog of thymidine. Biochim Biophys Acta. March; 32(1): 295–296.
  2. ^ Wilhelmus KR (2010). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". Cochrane Database Syst Rev 12: CD002898. doi:10.1002/14651858.CD002898.pub4. PMID 21154352. 
  3. ^ a b c d e f Goodman and Gilman's The Pharmacological Basis of Therapeutics. Edited by Gilman AG, Rall TW, Nies AS, Taylor P. McGraw-Hill. 8th ed. 1990.
  4. ^ Maxwell E. Treatment of herpes keratitis with 5-iodo-2-deoxyuridine (IDU): a clinical evaluation of 1500 cases. Am. J. Ophthalmol., 1963, 56, 571-573.
  5. ^ Drugs.com: Idoxuridine ophthalmic

Further Reading[edit]

  • Seth A, Misra A, Umrigar D (2004). "Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications". Pharm Dev Technol 9 (3): 277–289. doi:10.1081/PDT-200031432. PMID 15458233. 
  • Otto S (1998). "Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine)". J Intraven Nurs 21 (6): 335–7. PMID 10392098. 
  • Fauth E, Zankl H (1999). "Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting". Mutat Res 440 (2): 147–56. doi:10.1016/s1383-5718(99)00021-2. PMID 10209337.