Idoxuridine
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| 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. |
? |
| Legal status |
? |
| Routes |
topically |
| Identifiers |
| CAS number |
54-42-2  Y |
| ATC code |
D06BB01 J05AB02, S01AD01 |
| PubChem |
CID 5905 |
| DrugBank |
DB00249 |
| ChemSpider |
10481938 Y |
| UNII |
LGP81V5245 Y |
| KEGG |
D00342 Y |
| ChEMBL |
CHEMBL788  N |
| NIAID ChemDB |
001857 |
| Synonyms |
Iododeoxyuridine; IUdR |
| Chemical data |
| Formula |
C9H11IN2O5 |
| Mol. mass |
354.099 g/mol |
- I\C1=C\N(C(=O)NC1=O)C2C[C@H](O)[C@@H](CO)O2
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InChI=1S/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7?/m0/s1 Y
Key:XQFRJNBWHJMXHO-GFCOJPQKSA-N Y
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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]
Clinical use [edit]
Idoxuridine is mainly used topically to treat herpes simplex keratitis.[2] Epithelial lesions, especially initial attacks presenting with a dendritic ulcer, are most responsive to therapy, while infection with stromal involvement are less responsive.[3] Idoxuridine is ineffective against herpes simplex virus type 2 and varicella-zoster.[2]
Side effects [edit]
Common side effects of the eye drops include irritation, blurred vision and photophobia.[4] 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.[2] The dosage of the ointment is every 4 hours during day and once before bedtime.[2] 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.[2] Therapy is continued for 3-4 days after healing is complete, as demonstrated by fluorescein staining.[2]
See also [edit]
References [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. PMID 10209337.
- ^ Prusoff, W.H. (1959) Synthesis and biological activities of iododeoxyuridine, an analog of thymidine. Biochim Biophys Acta. March; 32(1): 295–296.
- ^ 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.
- ^ 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.
- ^ Drugs.com: Idoxuridine ophthalmic
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DNA-synthesis
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Nucleic acid inhibitors
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