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Properties

Spectra

Taxonomy

Idoxuridine

Targets (2)

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

Similar Structures

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
Unlock Additional Data
Dendrid	Solution / drops	1 mg/1mL	Ophthalmic	ALCON LABORATORIES, INC.	1963-06-28	1995-12-31
Herplex	Solution / drops		Ophthalmic	Allergan	1963-12-31	2011-08-04
Herplex D	Liquid		Topical	Allergan	1967-12-31	2011-08-04

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Sandoz Idoxuridine	Liquid		Topical	Sandoz Canada Incorporated	1999-02-15	2019-08-01

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands

Herpid (Astellas) / Herpidu (Ciba Vision) / Idulea (Elea) / Idustatin (Sanofi) / Keresid (GlaxoSmithKline) / Oftan IDU (Santen) / Virexen (Viñas)

Categories

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

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	other	Humans
UThymidine kinase	unknown	HHV-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

Drug Interactions: This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions: Not Available

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

D06BB01 — Idoxuridine

S01AD01 — Idoxuridine

AHFS Codes

84:04.06 — Antivirals
52:04.20 — Antivirals

PDB Entries

1ki7

MSDS

Download (73.5 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Unknown Status	Treatment	Leukemias	1

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
Liquid	Topical

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

Details1. DNA

Kind

Nucleotide

Organism

Humans

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.

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]

Details2. Thymidine kinase

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 January 16, 2020 21:25

Idoxuridine

Identification

Structure for Idoxuridine (DB00249)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References