Idoxuridine

Idoxuridine
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
category
  • US: C (Risk not ruled out)
  • B1 (topical), B3 (ophthalmologic) [AU]
Routes of
administration		 topically
Legal status
  • AU: S4 (Prescription only)
Identifiers
CAS Number 54-42-2 YesY
ATC code D06BB01 (WHO) J05AB02, S01AD01
PubChem CID 5905
DrugBank DB00249 YesY
ChemSpider 10481938 YesY
UNII LGP81V5245 YesY
KEGG D00342 YesY
ChEMBL CHEMBL788 N
NIAID ChemDB 001857
Synonyms Iododeoxyuridine; IUdR
Chemical data
Formula C9H11IN2O5
Molar mass 354.099 g/mol
 NYesY (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

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

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.

Formulations and dosage

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]

Synthesis

Idoxuridine synthesis: FR 1336866  GB 1024156  [6][7][8]

See also

References

  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. 1 2 3 4 5 6 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
  6. ↑ Prusoff, W. H. (1959). "Synthesis and biological activities of iododeoxyuridine, an analog of thymidine". Biochimica et Biophysica Acta 32 (1): 295–6. doi:10.1016/0006-3002(59)90597-9. PMID 13628760.
  7. ↑ Introduction of the 5-Halogenated Uracil Moiety into Deoxyribonucleic Acid of Mammalian Cells in Culture. L. Cheong, M. A. Rich, and M. L. Eidinoff J. Biol. Chem. 1960 235: 1441-1447.
  8. ↑ Chang, P. K.; Welch, A. D. (1963). "Iodination of 2'-Deoxycytidine and Related Substances1". Journal of Medicinal Chemistry 6 (4): 428. doi:10.1021/jm00340a019.

Further Reading

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