Idoxuridine

• Catalog No.: DB00249
• CAS Number: 54-42-2
• M. F.: C9H11IN2O5
• M. W.: 354.09851

SYNONYMS

• IUPAC name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: idoxuridine
• Brand Name: Idulea; Herpid; Heratil; Spectanefran; Antizona; Dendrid; Herplex Liquifilm; Idoxene; Kerecid; Stoxil; Synmiol; Virudox; Emanil; Herpe-Gel; Herpes-Gel; Herpesil; Herpidu; Herplex; Idexur; Idu Oculos; Iducher; Iduridin; Iduviran; Joddeoxiuridin; Ophthalmadine
• Synonyms: Iododeoxyridine; IUDR; ID2; Iodoxuridine; Idoxuridin; Idossuridina [DCIT]; 5IUDR; Allergan 211; IDUR; Idoxuridinum [INN-Latin]; Idoxuridina [INN-Spanish]; IDU; 5IDU; Allergan 201

DATABASE IDS

• PubChem CID: 5905
• CAS Number: 54-42-2
• PubChem SID: 46507573

PROPERTIES

• Hydrophobicity(logP): -0.5
• Solubility: <0.01 g/100 mL

DETAILS

Description (English)

• 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: Wikipedia; Drugs.com

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