Chemical: Drug
idoxuridine

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Overview

Generic Names
  • 5-iododeoxyuridine
  • 5IDU
  • 5IUDR
  • Allergan 201
  • Allergan 211
  • ID2
  • IDU
  • IDUR
  • IUDR
  • Idossuridina [DCIT]
  • Idoxuridin
  • Idoxuridina [INN-Spanish]
  • Idoxuridinum [INN-Latin]
  • Iododeoxyridine
  • Iodoxuridine
Trade Names
  • Antizona
  • Dendrid
  • Emanil
  • Heratil
  • Herpe-Gel
  • Herpes-Gel
  • Herpesil
  • Herpid
  • Herpidu
  • Herplex
  • Herplex Liquifilm
  • Idexur
  • Idoxene
  • Idu Oculos
  • Iducher
  • Idulea
  • Iduridin
  • Iduviran
  • Joddeoxiuridin
  • Kerecid
  • Ophthalmadine
  • Spectanefran
  • Stoxil
  • Synmiol
  • Virudox
Brand Mixture Names

PharmGKB Accession Id

PA164781019

Type(s):

Drug

Description

An analog of deoxyuridine that inhibits viral DNA synthesis. The drug is used as an antiviral agent.

Source: Drug Bank

Indication

For use in keratoconjunctivitis and keratitis caused by herpes simplex virus.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

Idoxuridine acts as an antiviral agent by inhibiting viral replication by substituting itself for thymidine in viral DNA. This in turn inhibits thymidylate phosphorylase and viral DNA polymerases from properly functioning. The effect of Idoxuridine results in the inability of the virus to reproduce or to infect/destroy tissue.

Source: Drug Bank

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.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Idoxuridine is rapidly inactivated by deaminases or nucleotidases.

Source: Drug Bank

Absorption

Systemic absorption is unlikely following ocular administration even when nasolacrimal secretions are swallowed, since vidarabine is rapidly deaminated in the gastrointestinal tract.

Source: Drug Bank

Toxicity

Hypersensitivity or increased sensitivity of eyes to light. LD 50=3080 mg/kg (orally in mice).

Source: Drug Bank

Chemical Properties

Chemical Formula

C9H11IN2O5

Source: Drug Bank

Isomeric SMILES

C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)I)CO)O

Source: Drug Bank

OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(I)C(=O)NC1=O

Source: Drug Bank

Canonical SMILES

OC[C@H]1O[C@H]

Source: Drug Bank

Average Molecular Weight

354.0985

Source: Drug Bank

Monoisotopic Molecular Weight

353.971264892

Source: Drug Bank

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(I)C(=O)NC1=O

Source: Drug Bank

InChI String

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

Source: Drug Bank

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
0065-0029-15
DrugBank:
DB00249
PDB:
ID2
ChEBI:
147675
KEGG Drug:
D00342
PubChem Compound:
5905
PubChem Substance:
46507573
7847408
Drugs Product Database (DPD):
2237187
ChemSpider:
5694
HET:
ID2
Therapeutic Targets Database:
DAP000997
FDA Drug Label at DailyMed:
3537dd95-954c-459f-97a9-54a861bed265

Clinical Trials

These are trials that mention idoxuridine and are related to either pharmacogenetics or pharmacogenomics.

No trials loaded.

NURSA Datasets

provided by nursa.org

No NURSA datasets available.

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Sources for PharmGKB drug information: DrugBank, PubChem.