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Identification
NameIdoxuridine
Accession NumberDB00249  (APRD00504, EXPT01835, DB03778)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
(+)-5-Iodo-2'-deoxyuridine
1-(2-Deoxy-beta-D-ribofuranosyl)-5-iodouracil
1-beta-D-2'-Deoxyribofuranosyl-5-iodouracil
1beta-D-2'-Deoxyribofuranosyl-5-iodouracil
2'-Deoxy-5-iodouridine
5-iodo-2'-deoxyuridine
5-Iododeoxyuridine
5-Iodouracil deoxyriboside
Idoxuridin
Idoxuridina
Idoxuridine
Idoxuridinum
IdU
Iododeoxyridine
Iodoxuridine
Joddeoxiuridin
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Herplexdrops.1 %ophthalmicAllergan Inc1963-12-312011-08-04Canada
Herplex Dliquid.1 %topicalAllergan Inc1967-12-312011-08-04Canada
Sandoz Idoxuridineliquid0.1 %topicalSandoz Canada Incorporated1999-02-15Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DendridAlcon
HerpidAstellas
HerpiduCiba Vision
IduleaElea
IdustatinSanofi
KeresidGlaxoSmithKline
Oftan IDUSanten
VirexenViñas
Brand mixturesNot Available
SaltsNot Available
Categories
UNIILGP81V5245
CAS number54-42-2
WeightAverage: 354.0985
Monoisotopic: 353.971264892
Chemical FormulaC9H11IN2O5
InChI KeyInChIKey=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
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[[email protected]]1O[[email protected]](C[C@@H]1O)N1C=C(I)C(=O)NC1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassPyrimidine 2'-deoxyribonucleosides
Direct ParentPyrimidine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside
  • Pyrimidone
  • Halopyrimidine
  • Pyrimidine
  • Hydropyrimidine
  • Saccharide
  • Aryl iodide
  • Aryl halide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor use in keratoconjunctivitis and keratitis caused by herpes simplex virus.
PharmacodynamicsIn 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 actionIdoxuridine 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.
Related Articles
AbsorptionSystemic absorption is unlikely following ocular administration even when nasolacrimal secretions are swallowed, since vidarabine is rapidly deaminated in the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Idoxuridine is rapidly inactivated by deaminases or nucleotidases.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityHypersensitivity or increased sensitivity of eyes to light. LD50=3080 mg/kg (orally in mice).
Affected organisms
  • Herpes simplex virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8129
Blood Brain Barrier+0.6502
Caco-2 permeable-0.8707
P-glycoprotein substrateNon-substrate0.7139
P-glycoprotein inhibitor INon-inhibitor0.8735
P-glycoprotein inhibitor IINon-inhibitor0.8719
Renal organic cation transporterNon-inhibitor0.8943
CYP450 2C9 substrateNon-substrate0.7834
CYP450 2D6 substrateNon-substrate0.8656
CYP450 3A4 substrateNon-substrate0.5445
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9108
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9093
CYP450 3A4 inhibitorNon-inhibitor0.8932
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8505
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7699
BiodegradationNot ready biodegradable0.9542
Rat acute toxicity2.0879 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9356
hERG inhibition (predictor II)Non-inhibitor0.8113
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Alcon laboratories inc
  • Allergan pharmaceutical
Packagers
Dosage forms
FormRouteStrength
Dropsophthalmic.1 %
Liquidtopical.1 %
Liquidtopical0.1 %
Prices
Unit descriptionCostUnit
Idoxuridine powder273.88USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point193British Patent 1,024,156.
water solubility2000 mg/L (at 25 °C)MERCK INDEX (1996)
logP-0.96NARURKAR,MM & MITRA,AK (1988)
Predicted Properties
PropertyValueSource
Water Solubility23.4 mg/mLALOGPS
logP-0.7ALOGPS
logP-0.53ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)8.06ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.1 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.4 m3·mol-1ChemAxon
Polarizability26.06 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

British Patent 1,024,156.

General References
  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:15458233 ]
  2. Otto SE: Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. [PubMed:10392098 ]
  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:10209337 ]
External Links
ATC CodesD06BB01J05AB02S01AD01
AHFS Codes
  • 52:04.20
  • 84:04.06
PDB Entries
FDA labelNot Available
MSDSDownload (73.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
other
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
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. doi: 10.1007/s11055-009-9237-0. Epub 2009 Dec 22. [PubMed:20033312 ]
  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:19178072 ]
Kind
Protein
Organism
HHV-1
Pharmacological action
unknown
Actions
unknown
General Function:
Thymidine kinase activity
Specific Function:
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.
Gene Name:
TK
Uniprot ID:
Q9QNF7
Molecular Weight:
40896.475 Da
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:9336833 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23