Substance

ID:134

Names and Identifiers
Synonyms
IDUIdoxuridina [INN-Spanish]Iodoxuridine5IUDRIdoxuridineIdoxuridinum [INN-Latin]Idossuridina [DCIT]Allergan 201Allergan 2115IDUIododeoxyridineIdoxuridinID2IDURIUDR
IUPAC Traditional name
idoxuridine
IUPAC name
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
Brand Name
AntizonaDendridHerpesilIduviranSpectanefranJoddeoxiuridinStoxilSynmiolHeratilHerpe-GelHerpidHerplex LiquifilmIdexurIducherVirudoxEmanilHerpiduIdoxeneIdu OculosIduleaHerplexIduridinKerecidOphthalmadineHerpes-Gel
Registration numbers
PubChem CID
CAS Number
PubChem SID
Properties
Physical Property
Hydrophobicity(logP)
-0.5
Solubility
<0.01 g/100 mL
Molecule Details
Drug Groups
approved
Description
An analog of deoxyuridine that inhibits viral DNA synthesis. The drug is used as an antiviral agent. [PubChem]
Indication
For use in keratoconjunctivitis and keratitis caused by herpes simplex virus.
Pharmacology
In chemical structure idoxuridine closely approximates the configuration of thymidine, one of the four building blocks of DNA (the genetic material of the Herpes virus). As a result, idoxuridine is able to replace thymidine in the enzymatic step of viral replication or "growth". The consequent production of faulty DNA results in a pseudostructure which cannot infect or destroy tissue. In short, by pre-empting a vital building block in the genetic material of the Herpes simplex virus, Herplex-D topical solution destroys the infective and destructive capacity of the viral material. The virus infected cell may only be attacked during the period of active synthesis of DNA. This occurs early in the development of the Herpes simplex lesion, but at different times in different cells. Therefore, ideally, the affected area should remain saturated with the antiviral agent.
Toxicity
Hypersensitivity or increased sensitivity of eyes to light. LD50=3080 mg/kg (orally in mice).
Affected Organisms
Herpes simplex virus
Biotransformation
Idoxuridine is rapidly inactivated by deaminases or nucleotidases.
Absorption
Systemic absorption is unlikely following ocular administration even when nasolacrimal secretions are swallowed, since vidarabine is rapidly deaminated in the gastrointestinal tract.
References
• Seth AK, Misra A, Umrigar D: Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications. Pharm Dev Technol. 2004 Aug;9(3):277-89. [Pubmed]
• Otto SE: Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. [Pubmed]
• Fauth E, Zankl H: Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting. Mutat Res. 1999 Apr 6;440(2):147-56. [Pubmed]
External Links
Molecular Spectra
No Data Available
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References
• Fauth E, Zankl H: Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting. Mutat Res. 1999 Apr 6;440(2):147-56. Pubmed
• Seth AK, Misra A, Umrigar D: Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications. Pharm Dev Technol. 2004 Aug;9(3):277-89. Pubmed
• Otto SE: Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. Pubmed