Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H11IN2O4 |
| Molecular Weight | 338.0991 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(I)C=NC2=O
InChI
InChIKey=XIJXHOVKJAXCGJ-XLPZGREQSA-N
InChI=1S/C9H11IN2O4/c10-5-2-11-9(15)12(3-5)8-1-6(14)7(4-13)16-8/h2-3,6-8,13-14H,1,4H2/t6-,7+,8+/m0/s1
| Molecular Formula | C9H11IN2O4 |
| Molecular Weight | 338.0991 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/31337643 | https://clinicaltrials.gov/ct2/show/NCT02993146 | https://clinicaltrials.gov/ct2/show/NCT02381561 | https://www.drugbank.ca/drugs/DB06485http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1316491/?page=1Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/31337643 | https://clinicaltrials.gov/ct2/show/NCT02993146 | https://clinicaltrials.gov/ct2/show/NCT02381561 | https://www.drugbank.ca/drugs/DB06485http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1316491/?page=1
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
Originator
Approval Year
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
139.03 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9661893/ |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:32:58 GMT 2025
by
admin
on
Mon Mar 31 18:32:58 GMT 2025
|
| Record UNII |
3HX21A3SQF
|
| Record Status |
Validated (UNII)
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| Record Version |
|
-
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Common Name | English | ||
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Code | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C798
Created by
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FDA ORPHAN DRUG |
519016
Created by
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FDA ORPHAN DRUG |
222606
Created by
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NCI_THESAURUS |
C1557
Created by
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FDA ORPHAN DRUG |
690919
Created by
admin on Mon Mar 31 18:32:58 GMT 2025 , Edited by admin on Mon Mar 31 18:32:58 GMT 2025
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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726188
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PRIMARY | |||
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C48813
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PRIMARY | |||
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3HX21A3SQF
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PRIMARY | |||
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C045889
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9840777
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PRIMARY | |||
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DB06485
Created by
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PRIMARY | |||
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DTXSID00239353
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PRIMARY | |||
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8831
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PRIMARY | |||
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SS-20
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93265-81-7
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CHEMBL2103821
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300000036831
Created by
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PRIMARY |
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ACTIVE MOIETY |
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