U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11IN2O5
Molecular Weight 354.0985
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IDOXURIDINE

SMILES

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

InChI

InChIKey=XQFRJNBWHJMXHO-RRKCRQDMSA-N
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

HIDE SMILES / InChI

Description

Idoxuridine is an antiviral agent use in keratitis caused by herpes simplex virus. As a prescription drug it comes as a 0.1% ophthalmic solution/drops (Herplex and Dendrid). The first studies of the compound for treatment of human herpes simplex started in early 1960s. Being a structural analog of thymidine idoxuridine inhibits viral DNA replication by substituting thymidine. The effect of idoxuridine results in the inability of the virus to reproduce and/or infect tissues. Idoxuridine also blocks viral thymidine kinase as its substrate analog.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
DENDRID
PMID

PMID

TitleDatePMID
Effect of cytosine, arabinoside, iododeoxyuridine, ethyldeoxyuridine, thiocyanatodeoxyuridine, and ribavirin on tail lesion formation in mice infected with vaccinia virus.
1976 Mar
Interventions for herpes simplex virus epithelial keratitis.
2003
Study on the possibility of insulin as a carrier of IUdR for hepatocellular carcinoma-targeted therapy.
2003 Aug
Exploration of the influence of 5-iodo-2'-deoxyuridine incorporation on the structure of d[CACG(IDU)G].
2003 Aug
Efficient one-step Suzuki arylation of unprotected halonucleosides, using water-soluble palladium catalysts.
2003 Aug 22
Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans.
2003 Aug 4
Postherpetic neuralgia.
2003 Dec
Dose-dependent pharmacokinetics of 1-(2-deoxy-beta-D- ribofuranosyl)-2,4-difluoro-5-iodobenzene: a potential mimic of 5-iodo-2'-deoxyuridine.
2003 Dec
[Anti-herpetic chemotherapeutic drugs].
2003 Feb
A balanced deoxyribonucleoside mixture increased the rate of DNA incorporation of 5-[125I]Iodo-2'-deoxyuridine in glioblastoma cells.
2003 Feb
Novel agents and strategies to treat herpes simplex virus infections.
2003 Feb
Preclinical Auger and gamma radiation dosimetry for fluorodeoxyuridine-enhanced tumour proliferation scintigraphy with [123I]iododeoxyuridine.
2003 Feb
Amino acid changes within conserved region III of the herpes simplex virus and human cytomegalovirus DNA polymerases confer resistance to 4-oxo-dihydroquinolines, a novel class of herpesvirus antiviral agents.
2003 Feb
Protease-activated receptor (PAR)-1 and PAR-2 participate in the cell growth of alveolar capillary endothelium in primary lung adenocarcinomas.
2003 Feb 1
Inhibition of base excision repair potentiates iododeoxyuridine-induced cytotoxicity and radiosensitization.
2003 Feb 15
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Biochemical and pharmacokinetic evaluation of a novel pyrimidine nucleoside nitric oxide donor as a potential anticancer/antiviral agent.
2003 Jul
Postherpetic neuralgia.
2003 Jun
Randomized, open-labelled comparison between an idoxuridine 10% gel and acyclovir 5% cream in recurrent herpes labialis.
2003 Mar
Clinical significance of atomic inner shell ionization (ISI) and Auger cascade for radiosensitization using IUdR, BUdR, platinum salts, or gadolinium porphyrin compounds.
2003 Mar 15
Functional expression of a sodium dependent nucleoside transporter on rabbit cornea: Role in corneal permeation of acyclovir and idoxuridine.
2003 Mar-Apr
A simple and efficient method for synthesis of 5-substituted 2'-deoxyuridine nucleosides using metal-halogen exchange reaction of 5-iodo-2'-deoxyuridine sodium salt.
2003 May 7
Design of Mycobacterium tuberculosis thymidine monophosphate kinase inhibitors.
2003 May-Aug
Biliary obstruction reduces hepatic killing and phagocytic clearance of circulating microorganisms in rats.
2003 May-Jun
Use of radiolabelled iododeoxyuridine as adjuvant treatment for experimental tumours of the liver.
2003 Oct
Role of MutSalpha in the recognition of iododeoxyuridine in DNA.
2003 Sep 1
Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides.
2004
In vitro efficacy of ganciclovir, cidofovir, penciclovir, foscarnet, idoxuridine, and acyclovir against feline herpesvirus type-1.
2004 Apr
Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications.
2004 Aug
Tracers to monitor the response to chemotherapy: in vitro screening of four radiopharmaceuticals.
2004 Aug
New tertiary constraints between the RNA components of active yeast spliceosomes: a photo-crosslinking study.
2004 Aug
Synchrotron radiation-based experimental determination of the optimal energy for cell radiotoxicity enhancement following photoelectric effect on stable iodinated compounds.
2004 Aug 2
Effects of single-pulse (< or = 1 ps) X-rays from laser-produced plasmas on mammalian cells.
2004 Dec
Neural stem cell detection, characterization, and age-related changes in the subventricular zone of mice.
2004 Feb 18
In vivo comparison of IVDU and IVFRU in HSV1-TK gene expressing tumor bearing rats.
2004 Jan
Suppression of generation and replication of acyclovir-resistant herpes simplex virus by a sensitive virus.
2004 Jan
Positive interactive radiosensitisation in vitro with the combination of two nucleoside analogues, (E)-2'-deoxy-2'-(fluoromethylene) cytidine and iododeoxyuridine.
2004 Jul
Continuous 28-day iododeoxyuridine infusion and hyperfractionated accelerated radiotherapy for malignant glioma: a phase I clinical study.
2004 Jul 15
Targeted radiosensitisation by pegylated liposome-encapsulated 3', 5'-O-dipalmitoyl 5-iodo-2'-deoxyuridine in a head and neck cancer xenograft model.
2004 Jul 19
Antiviral drugs in current clinical use.
2004 Jun
Antisense thymidylate synthase electrogene transfer to increase uptake of radiolabeled iododeoxyuridine in a murine model.
2004 Mar
Feasibility of sodium/iodide symporter gene as a new imaging reporter gene: comparison with HSV1-tk.
2004 Mar
[The latest in herpes simplex keratitis therapy].
2004 May
Indian hedgehog: a mechanotransduction mediator in condylar cartilage.
2004 May
The preparation of clinical grade 5-[123I]iodo-2'-deoxyuridine and 5-[125I]iodo-2'-deoxyuridine with high in vitro stability and the potential for early proliferation scintigraphy.
2004 May
Polyphosphoinositides-dependent regulation of the osteoclast actin cytoskeleton and bone resorption.
2004 May 13
Highly efficient DNA incorporation of intratumourally injected [125I]iododeoxyuridine under thymidine synthesis blocking in human glioblastoma xenografts.
2004 May 20
Synthesis and antiviral activities of 1'-carbon-substituted 4'-thiothymidines.
2004 Oct 15
[Therapeutic effect of 125IUdR on the glioma cell line C6 in vitro and in vivo].
2004 Sep
Overexpression of p27 Kip 1, probability of cell cycle exit, and laminar destination of neocortical neurons.
2005 Sep
Patent

Sample Use Guides

In Vivo Use Guide
1 drop (0.1% solution) every hour
Route of Administration: Topical
In Vitro Use Guide
Antiviral susceptibility of herpes simplex viruses by idoxuridine was studied in human culture cell line WI-38. Eight concentrations were tested, beginning with 1000 ug/ml and subsequent serial one-fourth dilutions. Mean MIC was 0.5 mg/ml.
Name Type Language
IDOXURIDINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
SK&F-14287
Code English
IDOXURIDINE [WHO-IP]
Common Name English
IDOXURIDINE [MART.]
Common Name English
IDOXURIDINE [INN]
Common Name English
IDOXURIDINE [EP]
Common Name English
IDOXURIDINE [HSDB]
Common Name English
DENDRID
Brand Name English
ALLERGAN 211
Code English
JODDEOXIURIDIN
Common Name English
SK&F 14287
Code English
IDU
Common Name English
IDOXURIDINUM [WHO-IP LATIN]
Common Name English
NSC-39661
Code English
HERPLEX
Brand Name English
STOXIL
Brand Name English
ALLERGAN-211
Code English
IODODEOXYURIDINE
Systematic Name English
IDOXURIDINE [VANDF]
Common Name English
5IUDR
Code English
IDOXURIDINE [USAN]
Common Name English
IDOXURIDINE [USP-RS]
Common Name English
5-IODO-2'-DEOXYURIDINE
Systematic Name English
IDOXURIDINE [MI]
Common Name English
URIDINE, 2'-DEOXY-5-IODO-
Systematic Name English
2'-DEOXY-5-IODOURIDINE
Systematic Name English
5-IUDR
Code English
IDOXURIDINE [ORANGE BOOK]
Common Name English
2'-DESOXY-5-IODOURIDINE
Systematic Name English
IDOXURIDINE [WHO-DD]
Common Name English
IDOXURIDINE [USP]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ05AB02
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
WHO-ATC S01AD01
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
WHO-ATC J05AB02
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
NDF-RT N0000175466
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
WHO-ATC D06BB01
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
WHO-VATC QS01AD01
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
WHO-VATC QD06BB01
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
Code System Code Type Description
INN
1486
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IDOXURIDINE
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY Description: A white or almost white, crystalline powder. Solubility: Slightly soluble in water, ethanol (~750 g/l) TS and hydrochloric acid (~70 g/l) TS; freely soluble in sodium hydroxide(~80 g/l) TS. Category: Anti-infective agent. Storage: Idoxuridine should be kept in a well-closed container, protected from light. Labeling: The designation Idoxuridine for sterile non-injectable use indicates that the substance complies with the additional requirement and may be used for sterile applications. Expiry date.Additional information: Melting temperature, about 180?C, with decomposition. Requirement: Idoxuridine contains not less than 98.0% and not more than 101.0% of C9H11IN2O5, calculated with reference to the dried substance.
EPA CompTox
54-42-2
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
DRUG BANK
DB00249
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
HSDB
54-42-2
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
PUBCHEM
5905
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY SWITZERF
MESH
D007065
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
MERCK INDEX
M6201
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY Merck Index
ECHA (EC/EINECS)
200-207-8
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
EVMPD
SUB08117MIG
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
RXCUI
5653
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY RxNorm
CAS
54-42-2
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
NCI_THESAURUS
C563
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
ChEMBL
CHEMBL788
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY
WIKIPEDIA
IDOXURIDINE
Created by admin on Tue Mar 06 12:00:17 UTC 2018 , Edited by admin on Tue Mar 06 12:00:17 UTC 2018
PRIMARY