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
DescriptionSources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1316491/?page=1https://www.ncbi.nlm.nih.gov/pubmed/31337643 | https://clinicaltrials.gov/ct2/show/NCT02993146 | https://clinicaltrials.gov/ct2/show/NCT02381561 | https://www.drugbank.ca/drugs/DB06485Curator'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: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1316491/?page=1https://www.ncbi.nlm.nih.gov/pubmed/31337643 | https://clinicaltrials.gov/ct2/show/NCT02993146 | https://clinicaltrials.gov/ct2/show/NCT02381561 | https://www.drugbank.ca/drugs/DB06485
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
Ropidoxuridine is a thymidine analogue and an oral prodrug of iododeoxyuridine that is easier to administer and less toxic with a more favorable therapeutic index in preclinical studies. Iododeoxyuridine demonstrated a survival advantage in Phase II studies in anaplastic astrocytoma, a type of brain tumor. Ropidoxuridine may help radiation therapy work better by making tumor cells more sensitive to the radiation therapy. In 2019, phase I clinical trials were ongoing to study the best dose of ropidoxuridine and its side effects in patients with metastatic malignant neoplasm in the brain and in patients with metastatic gastrointestinal cancer. First results showed that ropidoxuridine, combined with radiation therapy, was well-tolerated in patients with metastatic gastrointestinal cancer.
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 |
|---|---|---|
| Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). | 1998 Nov-Dec |
|
| Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting. | 1999 Apr 6 |
|
| Pert analysis of endogenous retroviruses induced from K-BALB mouse cells treated with 5-iododeoxyuridine: a potential strategy for detection of inducible retroviruses from vaccine cell substrates. | 2001 |
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| Laser cytometry of human tissues and tumors: proliferation and therapeutic applications. | 2001 |
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| Antiviral drugs: current state of the art. | 2001 Aug |
|
| ICCVAM evaluation of the murine local lymph node assay. Conclusions and recommendations of an independent scientific peer review panel. | 2001 Dec |
|
| In vitro effects of antiviral agents on human keratocytes. | 2001 Jan |
|
| Phase I trial of sequential administration of raltitrexed (Tomudex) and 5-iodo-2'-deoxyuridine (IdUrd). | 2001 May |
|
| Targeting DNA mismatch repair for radiosensitization. | 2001 Oct |
|
| Cytotoxicity of 125I-oestrogen decay in non-oestrogen receptor-expressing human breast cancer cells, MDA-231 and oestrogen receptor-expressing MCF-7 cells. | 2001 Sep |
|
| [Chromosomal abnormalities in lymphocytes from a patient with Werner's syndrome in intact culture and after treatment with halogenated analogs of thymidine]. | 2002 |
|
| HIF-1A, pimonidazole, and iododeoxyuridine to estimate hypoxia and perfusion in human head-and-neck tumors. | 2002 Dec 1 |
|
| Modelling the effect of incorporated halogenated pyrimidine on radiation-induced DNA strand breaks. | 2002 Nov |
|
| PET imaging drug distribution after intratumoral injection: the case for (124)I-iododeoxyuridine in malignant gliomas. | 2002 Nov |
|
| Quantitative detection of (125)IdU-induced DNA double-strand breaks with gamma-H2AX antibody. | 2002 Oct |
|
| Effect of 5-iodo-2'-deoxyuridine on vaccinia virus (orthopoxvirus) infections in mice. | 2002 Sep |
|
| 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 |
|
| 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 |
|
| Preclinical Auger and gamma radiation dosimetry for fluorodeoxyuridine-enhanced tumour proliferation scintigraphy with [123I]iododeoxyuridine. | 2003 Feb |
|
| In vitro activity of potential anti-poxvirus agents. | 2003 Jan |
|
| Biliary obstruction reduces hepatic killing and phagocytic clearance of circulating microorganisms in rats. | 2003 May-Jun |
|
| 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 |
|
| Suppression of generation and replication of acyclovir-resistant herpes simplex virus by a sensitive virus. | 2004 Jan |
|
| Antiviral drugs in current clinical use. | 2004 Jun |
|
| 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 |
|
| [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 |
Sample Use Guides
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NCI_THESAURUS |
C798
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FDA ORPHAN DRUG |
519016
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FDA ORPHAN DRUG |
222606
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NCI_THESAURUS |
C1557
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FDA ORPHAN DRUG |
690919
Created by
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726188
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C48813
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3HX21A3SQF
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C045889
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9840777
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DB06485
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DTXSID00239353
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8831
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SS-20
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93265-81-7
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CHEMBL2103821
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300000036831
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ACTIVE MOIETY
SUBSTANCE RECORD
