Chemistry:Idoxuridine
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| Other names | Iododeoxyuridine; IUdR |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| MedlinePlus | a601062 |
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| Routes of administration | topically |
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| Formula | C9H11IN2O5 |
| Molar mass | 354.100 g·mol−1 |
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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]
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.[citation needed]
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
See also
- Trifluridine
- Acyclovir
- Foscarnet
References
- ↑ 1.0 1.1 "Synthesis and biological activities of iododeoxyuridine, an analog of thymidine". Biochimica et Biophysica Acta 32 (1): 295–296. March 1959. doi:10.1016/0006-3002(59)90597-9. PMID 13628760.
- ↑ "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". The Cochrane Database of Systematic Reviews 1: CD002898. January 2015. doi:10.1002/14651858.CD002898.pub5. PMID 25879115.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 Goodman and Gilman's The Pharmacological Basis of Therapeutics. Edited by Gilman AG, Rall TW, Nies AS, Taylor P. McGraw-Hill. 8th ed. 1990.
- ↑ "Treatment of herpes keratitis with 5-iodo-2-deoxyuridine (IDU): a clinical evaluation of 1500 cases". American Journal of Ophthalmology 56: 571–573. October 1963. doi:10.1016/0002-9394(63)90006-0. PMID 14070708.
- ↑ Drugs.com: Idoxuridine ophthalmic
- ↑ Gaston A, Vesperto T, "Nouveau procédé de préparation d'un dérivé de l'uridine et produits utilisés dans ce procédé [New process for preparing a derivative of uridine and products used in this process]", FR patent 1336866, published 1963-09-06, assigned to Roussel-Uclaf
- ↑ "Process for the preparation of 5-iodo-2'-desoxy-uridine" GB patent 1024156, published 1966-03-30, assigned to Roussel-Uclaf
- ↑ "Introduction of the 5-halogenated uracil moiety into deoxyribonucleic acid of mammalian cells in culture". The Journal of Biological Chemistry 235 (5): 1441–1447. May 1960. doi:10.1016/S0021-9258(18)69427-X. PMID 13809628.
- ↑ "Iodination of 2'-Deoxycytidine and Related Substances". Journal of Medicinal Chemistry 6 (4): 428–430. July 1963. doi:10.1021/jm00340a019. PMID 14184899.
Further reading
- "Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications". Pharmaceutical Development and Technology 9 (3): 277–289. August 2004. doi:10.1081/PDT-200031432. PMID 15458233.
- "Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine)". Journal of Intravenous Nursing 21 (6): 335–337. 1998. PMID 10392098.
- "Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting". Mutation Research 440 (2): 147–156. April 1999. doi:10.1016/s1383-5718(99)00021-2. PMID 10209337.
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