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

Molecular Formula C9H11IN2O5
Molecular Weight 354.0985
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm; http://www.ncbi.nlm.nih.gov/pubmed/9336833; http://www.ncbi.nlm.nih.gov/pubmed/12705773; http://www.ncbi.nlm.nih.gov/pubmed/14435162; http://www.ncbi.nlm.nih.gov/pubmed/4309419

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

Curator's Comment: In rat brain

Originator

Curator's Comment: Late 1950s

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2366042
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DENDRID

Approved Use

For the treatment of keratitis caused by the virus of herpes simplex.

Launch Date

1963
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
139.03 μM × h
4538 mg/m² 1 times / day multiple, intraperitoneal
dose: 4538 mg/m²
route of administration: Intraperitoneal
experiment type: MULTIPLE
co-administered:
IDOXURIDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
5-iodo-2-pyrimidinone-2'-deoxyribose-mediated cytotoxicity and radiosensitization in U87 human glioblastoma xenografts.
2007-11-15
IPdR: a novel oral radiosensitizer.
2007-09
Overexpression of p27 Kip 1, probability of cell cycle exit, and laminar destination of neocortical neurons.
2005-09
Effects of single-pulse (< or = 1 ps) X-rays from laser-produced plasmas on mammalian cells.
2004-12
Synthesis and antiviral activities of 1'-carbon-substituted 4'-thiothymidines.
2004-10-15
[Therapeutic effect of 125IUdR on the glioma cell line C6 in vitro and in vivo].
2004-09
Synchrotron radiation-based experimental determination of the optimal energy for cell radiotoxicity enhancement following photoelectric effect on stable iodinated compounds.
2004-08-02
Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications.
2004-08
Tracers to monitor the response to chemotherapy: in vitro screening of four radiopharmaceuticals.
2004-08
New tertiary constraints between the RNA components of active yeast spliceosomes: a photo-crosslinking study.
2004-08
Targeted radiosensitisation by pegylated liposome-encapsulated 3', 5'-O-dipalmitoyl 5-iodo-2'-deoxyuridine in a head and neck cancer xenograft model.
2004-07-19
Continuous 28-day iododeoxyuridine infusion and hyperfractionated accelerated radiotherapy for malignant glioma: a phase I clinical study.
2004-07-15
Positive interactive radiosensitisation in vitro with the combination of two nucleoside analogues, (E)-2'-deoxy-2'-(fluoromethylene) cytidine and iododeoxyuridine.
2004-07
Antiviral drugs in current clinical use.
2004-06
Highly efficient DNA incorporation of intratumourally injected [125I]iododeoxyuridine under thymidine synthesis blocking in human glioblastoma xenografts.
2004-05-20
Polyphosphoinositides-dependent regulation of the osteoclast actin cytoskeleton and bone resorption.
2004-05-13
[The latest in herpes simplex keratitis therapy].
2004-05
Indian hedgehog: a mechanotransduction mediator in condylar cartilage.
2004-05
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.
2004-05
In vitro efficacy of ganciclovir, cidofovir, penciclovir, foscarnet, idoxuridine, and acyclovir against feline herpesvirus type-1.
2004-04
Antisense thymidylate synthase electrogene transfer to increase uptake of radiolabeled iododeoxyuridine in a murine model.
2004-03
Feasibility of sodium/iodide symporter gene as a new imaging reporter gene: comparison with HSV1-tk.
2004-03
Neural stem cell detection, characterization, and age-related changes in the subventricular zone of mice.
2004-02-18
In vivo comparison of IVDU and IVFRU in HSV1-TK gene expressing tumor bearing rats.
2004-01
Suppression of generation and replication of acyclovir-resistant herpes simplex virus by a sensitive virus.
2004-01
Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides.
2004
Postherpetic neuralgia.
2003-12
Dose-dependent pharmacokinetics of 1-(2-deoxy-beta-D- ribofuranosyl)-2,4-difluoro-5-iodobenzene: a potential mimic of 5-iodo-2'-deoxyuridine.
2003-12
Design of Mycobacterium tuberculosis thymidine monophosphate kinase inhibitors.
2003-10-21
Use of radiolabelled iododeoxyuridine as adjuvant treatment for experimental tumours of the liver.
2003-10
Role of MutSalpha in the recognition of iododeoxyuridine in DNA.
2003-09-01
Efficient one-step Suzuki arylation of unprotected halonucleosides, using water-soluble palladium catalysts.
2003-08-22
Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans.
2003-08-04
Study on the possibility of insulin as a carrier of IUdR for hepatocellular carcinoma-targeted therapy.
2003-08
Exploration of the influence of 5-iodo-2'-deoxyuridine incorporation on the structure of d[CACG(IDU)G].
2003-08
Biochemical and pharmacokinetic evaluation of a novel pyrimidine nucleoside nitric oxide donor as a potential anticancer/antiviral agent.
2003-07
Functional expression of a sodium dependent nucleoside transporter on rabbit cornea: Role in corneal permeation of acyclovir and idoxuridine.
2003-06-20
Postherpetic neuralgia.
2003-06
Biliary obstruction reduces hepatic killing and phagocytic clearance of circulating microorganisms in rats.
2003-05-24
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.
2003-05-07
Clinical significance of atomic inner shell ionization (ISI) and Auger cascade for radiosensitization using IUdR, BUdR, platinum salts, or gadolinium porphyrin compounds.
2003-03-15
Randomized, open-labelled comparison between an idoxuridine 10% gel and acyclovir 5% cream in recurrent herpes labialis.
2003-03
Inhibition of base excision repair potentiates iododeoxyuridine-induced cytotoxicity and radiosensitization.
2003-02-15
[Anti-herpetic chemotherapeutic drugs].
2003-02
A balanced deoxyribonucleoside mixture increased the rate of DNA incorporation of 5-[125I]Iodo-2'-deoxyuridine in glioblastoma cells.
2003-02
Novel agents and strategies to treat herpes simplex virus infections.
2003-02
Preclinical Auger and gamma radiation dosimetry for fluorodeoxyuridine-enhanced tumour proliferation scintigraphy with [123I]iododeoxyuridine.
2003-02
In vitro activity of potential anti-poxvirus agents.
2003-01
Interventions for herpes simplex virus epithelial keratitis.
2003
Effect of cytosine, arabinoside, iododeoxyuridine, ethyldeoxyuridine, thiocyanatodeoxyuridine, and ribavirin on tail lesion formation in mice infected with vaccinia virus.
1976-03
Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:47:40 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:40 GMT 2025
Record UNII
LGP81V5245
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DENDRID
Preferred Name English
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 [HSDB]
Common Name English
ALLERGAN211
Code English
JODDEOXIURIDIN
Common Name English
IDOXURIDINE [USP MONOGRAPH]
Common Name English
IDOXURIDINE [USP IMPURITY]
Common Name English
SK&F 14287
Code English
IDU
Common Name English
IDOXURIDINUM [WHO-IP LATIN]
Common Name English
IDOXURIDINE [EP MONOGRAPH]
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 [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
Idoxuridine [WHO-DD]
Common Name English
5-IUDR
Code English
IDOXURIDINE [ORANGE BOOK]
Common Name English
IDOXURIDINE [JAN]
Common Name English
2'-DESOXY-5-IODOURIDINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
WHO-VATC QJ05AB02
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
WHO-ATC S01AD01
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
WHO-ATC J05AB02
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
NDF-RT N0000175466
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
WHO-ATC D06BB01
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
NCI_THESAURUS C281
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
FDA ORPHAN DRUG 95696
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
WHO-VATC QS01AD01
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
WHO-VATC QD06BB01
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
Code System Code Type Description
NSC
39661
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
SMS_ID
100000083677
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
INN
1486
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IDOXURIDINE
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
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.
DAILYMED
LGP81V5245
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID2045238
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
FDA UNII
LGP81V5245
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
DRUG BANK
DB00249
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
HSDB
7479
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
PUBCHEM
5905
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
MESH
D007065
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
DRUG CENTRAL
1417
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
MERCK INDEX
m6201
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
200-207-8
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PRIMARY
EVMPD
SUB08117MIG
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PRIMARY
RS_ITEM_NUM
1336001
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PRIMARY
CHEBI
147675
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PRIMARY
RXCUI
5653
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PRIMARY RxNorm
CAS
54-42-2
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PRIMARY
NCI_THESAURUS
C563
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
ChEMBL
CHEMBL788
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
WIKIPEDIA
IDOXURIDINE
Created by admin on Mon Mar 31 17:47:40 GMT 2025 , Edited by admin on Mon Mar 31 17:47:40 GMT 2025
PRIMARY
Related Record Type Details
LABELED -> NON-LABELED
SOLVATE->ANHYDROUS
LABELED -> NON-LABELED
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY