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Idoxuridine

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Title: Idoxuridine  
Author: World Heritage Encyclopedia
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Subject: Thymidine kinase from herpesvirus, Brivudine, Trifluridine, Edoxudine, Resiquimod
Collection: Anti-Herpes Virus Drugs, Nucleosides, Organoiodides, Pyrimidinediones
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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
MedlinePlus
Pregnancy
category
  • US: C (Risk not ruled out)
  • B1 (topical), B3 (ophthalmologic) [AU]
Legal status
Routes of
administration
topically
Identifiers
CAS Registry Number  YesY
ATC code D06 J05, S01
PubChem CID:
DrugBank  YesY
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEMBL  N
NIAID ChemDB
Synonyms Iododeoxyuridine; IUdR
Chemical data
Formula C9H11IN2O5
Molecular mass 354.099 g/mol
 N   

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]

Contents

  • Clinical use 1
  • Side effects 2
  • Formulations and dosage 3
  • Synthesis 4
  • See also 5
  • References 6
  • Further Reading 7

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. ^
  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
  6. ^
  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. ^

Further Reading

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