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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdoxuridine
Identification
- Name
- Idoxuridine
- Accession Number
- DB00249 (APRD00504, EXPT01835, DB03778)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
An analog of deoxyuridine that inhibits viral DNA synthesis. The drug is used as an antiviral agent.
- Structure
Structure for Idoxuridine (DB00249)
- 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 IDs
- ALLERGAN 211 / ALLERGAN-211 / NSC-39661 / SK&F 14287
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Dendrid Solution / drops 1 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1963-06-28 1995-12-31 US 
Herplex Solution / drops .1 % Ophthalmic Allergan 1963-12-31 2011-08-04 Canada 
Herplex D Liquid .1 % Topical Allergan 1967-12-31 2011-08-04 Canada Sandoz Idoxuridine Liquid 0.1 % Topical Sandoz Canada Incorporated 1999-02-15 Not applicable Canada - International/Other Brands
- Herpid (Astellas) / Herpidu (Ciba Vision) / Idulea (Elea) / Idustatin (Sanofi) / Keresid (GlaxoSmithKline) / Oftan IDU (Santen) / Virexen (Viñas)
- Categories
- Anti-Infective Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Carbohydrates
- Deoxyribonucleosides
- Deoxyuridine
- Dermatologicals
- Direct Acting Antivirals
- Enzyme Inhibitors
- Glycosides
- Nucleic Acid Synthesis Inhibitors
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleoside Analog Antiviral
- Nucleosides
- Nucleosides and Nucleotides Excl. Reverse Transcriptase Inhibitors
- Ophthalmologicals
- Pyrimidine Nucleosides
- Pyrimidines
- Ribonucleosides
- Sensory Organs
- Uridine
- UNII
- LGP81V5245
- CAS number
- 54-42-2
- Weight
- Average: 354.0985
Monoisotopic: 353.971264892 - Chemical Formula
- C9H11IN2O5
- InChI Key
- 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[C@H]1O[C@H](C[C@@H]1O)N1C=C(I)C(=O)NC1=O
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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.
Target Actions Organism ADNA otherHumans UThymidine kinase unknownHHV-1 - 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
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
References
- Synthesis Reference
British Patent 1,024,156.
- General 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:15458233]
- Otto SE: Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. [PubMed:10392098]
- 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
- Human Metabolome Database
- HMDB0014394
- KEGG Drug
- D00342
- PubChem Compound
- 5905
- PubChem Substance
- 46507573
- ChemSpider
- 5694
- BindingDB
- 50370388
- ChEBI
- 147675
- ChEMBL
- CHEMBL788
- Therapeutic Targets Database
- DAP000997
- PharmGKB
- PA164781019
- HET
- ID2
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Idoxuridine
- ATC Codes
- J05AB02 — Idoxuridine
- J05AB — Nucleosides and nucleotides excl. reverse transcriptase inhibitors
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- D06BB — Antivirals
- D06B — CHEMOTHERAPEUTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- AHFS Codes
- 52:04.20 — Antivirals
- 84:04.06 — Antivirals
- PDB Entries
- 1ki7
- MSDS
- Download (73.5 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Glaxosmithkline
- Alcon laboratories inc
- Allergan pharmaceutical
- Packagers
- Medisca Inc.
- Dosage forms
Form Route Strength Solution / drops Ophthalmic 1 mg/1mL Solution / drops Ophthalmic .1 % Liquid Topical .1 % Liquid Topical 0.1 % - Prices
Unit description Cost Unit Idoxuridine powder 273.88USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 193 British Patent 1,024,156. water solubility 2000 mg/L (at 25 °C) MERCK INDEX (1996) logP -0.96 NARURKAR,MM & MITRA,AK (1988) - Predicted Properties
Property Value Source Water Solubility 23.4 mg/mL ALOGPS logP -0.7 ALOGPS logP -0.53 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 8.46 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 99.1 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 64.4 m3·mol-1 ChemAxon Polarizability 26.17 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.8129 Blood Brain Barrier + 0.6502 Caco-2 permeable - 0.8707 P-glycoprotein substrate Non-substrate 0.7139 P-glycoprotein inhibitor I Non-inhibitor 0.8735 P-glycoprotein inhibitor II Non-inhibitor 0.8719 Renal organic cation transporter Non-inhibitor 0.8943 CYP450 2C9 substrate Non-substrate 0.7834 CYP450 2D6 substrate Non-substrate 0.8656 CYP450 3A4 substrate Non-substrate 0.5445 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9108 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9093 CYP450 3A4 inhibitor Non-inhibitor 0.8932 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8505 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.7699 Biodegradation Not ready biodegradable 0.9542 Rat acute toxicity 2.0879 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9356 hERG inhibition (predictor II) Non-inhibitor 0.8113
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Pyrimidine nucleosides
- Sub Class
- Pyrimidine 2'-deoxyribonucleosides
- Direct Parent
- Pyrimidine 2'-deoxyribonucleosides
- Alternative Parents
- Pyrimidones / Halopyrimidines / Hydroxypyrimidines / Aryl iodides / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds show 6 more
- Substituents
- Pyrimidine 2'-deoxyribonucleoside / Halopyrimidine / Hydroxypyrimidine / Pyrimidone / Aryl halide / Aryl iodide / Hydropyrimidine / Pyrimidine / Heteroaromatic compound / Tetrahydrofuran show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organoiodine compound, pyrimidine 2'-deoxyribonucleoside (CHEBI:147675)
Targets
1. DNA
Yes
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
- 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]
- 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 the...
- Gene Name
- TK
- Uniprot ID
- Q9QNF7
- Uniprot Name
- Thymidine kinase
- Molecular Weight
- 40896.475 Da
References
- 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]
Drug created on June 13, 2005 07:24 / Updated on April 18, 2019 06:15