Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Idoxuridine: Difference between pages

{{short description|Chemical compound}}

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| pregnancy_category = B1 (topical), B3 (ophthalmologic) [AU]

| pregnancy_US = C

| legal_AU = S4

| legal_status = Rx-only

| routes_of_administration = [[topically]]

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| NIAID_ChemDB = 001857

| ChEMBL = 788

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| C=9 | H=11 | I=1 | N=2 | O=5

'''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 pair]]ing. It is used only topically due to cardiotoxicity. It was synthesized by [[William Prusoff]] in the late 1950s.<ref name=Prusoff /> Initially developed as an anticancer drug, idoxuridine became the first antiviral agent in 1962.<ref name="Wilhelmus">{{cite journal | vauthors = Wilhelmus KR | title = Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis | journal = The Cochrane Database of Systematic Reviews | volume = 1 | pages = CD002898 | date = January 2015 | pmid = 25879115 | pmc = 4443501 | doi = 10.1002/14651858.CD002898.pub5 }}</ref>

==Clinical use==

Idoxuridine is mainly used topically to treat [[herpes simplex]] [[keratitis]].<ref name="Goodman">Goodman and Gilman's The Pharmacological Basis of Therapeutics. Edited by Gilman AG, Rall TW, Nies AS, Taylor P. McGraw-Hill. 8th ed. 1990.</ref> Epithelial lesions, especially initial attacks presenting with a dendritic ulcer, are most responsive to therapy, while infection with stromal involvement are less responsive.<ref>{{cite journal | vauthors = Maxwell E | title = Treatment of herpes keratitis with 5-iodo-2-deoxyuridine (IDU): a clinical evaluation of 1500 cases | journal = American Journal of Ophthalmology | volume = 56 | pages = 571–573 | date = October 1963 | pmid = 14070708 | doi = 10.1016/0002-9394(63)90006-0 }}</ref> Idoxuridine is ineffective against herpes simplex virus type 2 and [[varicella-zoster]].<ref name="Goodman"/>

==Side effects==

Common side effects of the eye drops include irritation, blurred vision and [[photophobia]].<ref>Drugs.com: [https://www.drugs.com/mtm/idoxuridine-ophthalmic.html Idoxuridine ophthalmic]</ref> [[Cornea]]l clouding and damage of the corneal epithelium may also occur.{{citation needed|date=February 2012}}

==Formulations and dosage==

Idoxuridine is available as either a 0.5% ophthalmic [[ointment]] or as a 0.1% ophthalmic [[Solution (chemistry)|solution]].<ref name="Goodman"/> The dosage of the ointment is every 4 hours during day and once before bedtime.<ref name="Goodman"/> The dosage of the solution is 1 drop in the [[conjunctiva|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.<ref name="Goodman"/> Therapy is continued for 3–4 days after healing is complete, as demonstrated by [[fluorescein]] staining.<ref name="Goodman"/>

==Synthesis==

[[File:Idoxuridine synthesis.svg|thumb|center|500px|Idoxuridine synthesis.<ref name=Prusoff>{{cite journal | vauthors = Prusoff WH | title = Synthesis and biological activities of iododeoxyuridine, an analog of thymidine | journal = Biochimica et Biophysica Acta | volume = 32 | issue = 1 | pages = 295–296 | date = March 1959 | pmid = 13628760 | doi = 10.1016/0006-3002(59)90597-9 | doi-access = free }}</ref><ref>{{Cite patent|country=FR|number=1336866|pubdate=1963-09-06|title=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]|assign1=[[Roussel-Uclaf]]|inventor = Gaston A, Vesperto T }}</ref><ref>{{Cite patent|country=GB|number=1024156|pubdate=1966-03-30|title=Process for the preparation of 5-iodo-2'-desoxy-uridine|assign1=[[Roussel-Uclaf]]}}</ref><ref>{{cite journal | vauthors = Cheong L, Rich MA, Eidinoff ML | title = Introduction of the 5-halogenated uracil moiety into deoxyribonucleic acid of mammalian cells in culture | journal = The Journal of Biological Chemistry | volume = 235 | issue = 5 | pages = 1441–1447 | date = May 1960 | pmid = 13809628 | doi = 10.1016/S0021-9258(18)69427-X | doi-access = free }}</ref><ref>{{cite journal | vauthors = Chang PK, Welch AD | title = Iodination of 2'-Deoxycytidine and Related Substances | journal = Journal of Medicinal Chemistry | volume = 6 | issue = 4 | pages = 428–430 | date = July 1963 | pmid = 14184899 | doi = 10.1021/jm00340a019 }}</ref>]]

== See also ==

* [[Trifluridine]]

* [[Acyclovir]]

* [[Foscarnet]]

== References ==

{{reflist}}

== Further reading ==

{{refbegin}}

* {{cite journal | vauthors = Seth AK, Misra A, Umrigar D | title = Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications | journal = Pharmaceutical Development and Technology | volume = 9 | issue = 3 | pages = 277–289 | date = August 2004 | pmid = 15458233 | doi = 10.1081/PDT-200031432 | s2cid = 33864681 }}

* {{cite journal | vauthors = Otto SE | title = Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine) | journal = Journal of Intravenous Nursing | volume = 21 | issue = 6 | pages = 335–337 | year = 1998 | pmid = 10392098 }}

* {{cite journal | vauthors = Fauth E, Zankl H | title = Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting | journal = Mutation Research | volume = 440 | issue = 2 | pages = 147–156 | date = April 1999 | pmid = 10209337 | doi = 10.1016/s1383-5718(99)00021-2 }}

{{refend}}

<!-- Discovered in 1950 -->

{{Antibiotics and chemotherapeutics for dermatological use}}

{{Antivirals}}

{{Ophthalmological anti-infectives}}

[[Category:Nucleosides]]

[[Category:Pyrimidinediones]]

[[Category:Organoiodides]]

[[Category:Anti-herpes virus drugs]]

[[Category:Hydroxymethyl compounds]]