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Identification
Name Idoxuridine
Accession Number DB00249 (APRD00504, DB03778, EXPT01835)
Type small molecule
Groups approved
Description

An analog of deoxyuridine that inhibits viral DNA synthesis. The drug is used as an antiviral agent. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • 5-Iododeoxyuridine
  • 5IDU
  • 5IUDR
  • Allergan 201
  • Allergan 211
  • ID2
  • Idossuridina [DCIT]
  • Idoxuridin
  • IDU
  • IDUR
  • Iododeoxyridine
  • Iodoxuridine
  • IUDR
Brand 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 name mixtures Not Available
Categories
  • Antiviral Agents
  • Nucleic Acid Synthesis Inhibitors
CAS number 54-42-2
Weight Average: 354.0985
Monoisotopic: 353.971264892
Chemical Formula C9H11IN2O5
InChI Key InChIKey=XQFRJNBWHJMXHO-RRKCRQDMSA-N
InChI
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
Plain Text
IUPAC Name
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(I)C(=O)NC1=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Glycerol and Derivatives
  • Pyrimidines and Derivatives
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Ethers
  • Aryl Halides
  • Alcohols and Polyols
  • Pyrimidines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Furans
  • Cyanamides
Pharmacology
Indication For use in keratoconjunctivitis and keratitis caused by herpes simplex virus.
Pharmacodynamics 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.
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.
Absorption Systemic absorption is unlikely following ocular administration even when nasolacrimal secretions are swallowed, since vidarabine is rapidly deaminated in the gastrointestinal tract.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Idoxuridine is rapidly inactivated by deaminases or nucleotidases.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Hypersensitivity or increased sensitivity of eyes to light. LD50=3080 mg/kg (orally in mice).
Affected organisms
  • Herpes simplex virus
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Alcon laboratories inc
  • Allergan pharmaceutical
Packagers
Dosage forms
Form Route Strength
Liquid Topical
Solution / drops Ophthalmic
Prices
Unit description Cost Unit
Idoxuridine powder 273.88 USD g
Patents Not Available
Properties
State solid
Melting point 164-166
Experimental Properties
Property Value Source
water solubility <0.01 g/100 mL PhysProp
logP -0.5 PhysProp
Predicted Properties
Property Value Source
water solubility 2.34e+01 g/l ALOGPS
logP -0.70 ALOGPS
logP -0.53 ChemAxon Molconvert
logS -1.18 ALOGPS
pKa 13.91 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 99.10 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 64.40 ChemAxon Molconvert
polarizability 26.06 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. 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
  2. Otto SE: Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. Pubmed
  3. 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
Resource Link
KEGG Drug D00342 Link_out
PubChem Compound 5905 Link_out
PubChem Substance 46507573 Link_out
ChemSpider 5694 Link_out
ChEBI 147675 Link_out
ChEMBL 147675 Link_out
Therapeutic Targets Database DAP000997 Link_out
PharmGKB PA449963 Link_out
HET ID2 Link_out
Drug Product Database 2237187 Link_out
Drugs.com http://www.drugs.com/mtm/idoxuridine-ophthalmic.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Idoxuridine Link_out
ATC Codes
  • D06BB01
  • J05AB02
  • S01AD01
AHFS Codes
  • 52:04.20
  • 84:04.06
PDB Entries
FDA label Not Available
MSDS show (73.5 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. DNA

Pharmacological action: yes
Actions: other

DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Gene Sequence: FASTA

References:
  1. Komissarova NV, Tiunova AA, Anokhin KV: Selective impairments to memory consolidation in chicks produced by 5’-iodo-2’-deoxyuridine. Neurosci Behav Physiol. 2010 Feb;40(2):215-23. Epub 2009 Dec 22. Pubmed
  2. Komissarova NV, Tiunova AA, Anokhin KV: [Selective disruption of memory consolidation in chicks produced by 5’-iodo-2’-deoxyuridine] Zh Vyssh Nerv Deiat Im I P Pavlova. 2008 Nov-Dec;58(6):700-10. Pubmed

2. Thymidine kinase

Pharmacological action: unknown
Actions: unknown

In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate their genome

Organism class: viral
UniProt ID: Q9QNF7 Link_out
Gene: TK
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wild K, Bohner T, Folkers G, Schulz GE: The structures of thymidine kinase from herpes simplex virus type 1 in complex with substrates and a substrate analogue. Protein Sci. 1997 Oct;6(10):2097-106. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on October 11, 2011 10:31

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.