Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H11IN2O5.H2O |
| Molecular Weight | 372.1138 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(I)C(=O)NC2=O
InChI
InChIKey=JWEOOFXTRSOJNN-VWZUFWLJSA-N
InChI=1S/C9H11IN2O5.H2O/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);1H2/t5-,6+,7+;/m0./s1
| 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 |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| Antiviral drugs: current state of the art. | 2001 Aug |
|
| Preclinical evaluation of locoregional delivery of radiolabeled iododeoxyuridine and thymidylate synthase inhibitor in a hepatoma model. | 2001 Feb |
|
| Increased glomerular Vwf after kidney irradiation is not due to increased biosynthesis or endothelial cell proliferation. | 2001 Jul |
|
| Phase I trial of sequential administration of raltitrexed (Tomudex) and 5-iodo-2'-deoxyuridine (IdUrd). | 2001 May |
|
| Contact dermatitis from topical antiviral drugs. | 2001 May |
|
| Targeting DNA mismatch repair for radiosensitization. | 2001 Oct |
|
| [Chromosomal abnormalities in lymphocytes from a patient with Werner's syndrome in intact culture and after treatment with halogenated analogs of thymidine]. | 2002 |
|
| Pharmacokinetics and metabolism of the novel synthetic C-nucleoside, 1-(2-deoxy-beta-D-ribofuranosyl)-2,4-difluoro-5-iodobenzene: a potential mimic of 5-iodo-2'-deoxyuridine. | 2002 Apr |
|
| Dimethyl sulfoxide blocks herpes simplex virus-1 productive infection in vitro acting at different stages with positive cooperativity. Application of micro-array analysis. | 2002 May 24 |
|
| Modelling the effect of incorporated halogenated pyrimidine on radiation-induced DNA strand breaks. | 2002 Nov |
|
| Effect of 5-iodo-2'-deoxyuridine on vaccinia virus (orthopoxvirus) infections in mice. | 2002 Sep |
|
| Interventions for herpes simplex virus epithelial keratitis. | 2003 |
|
| 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 |
|
| 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 |
|
| Design of Mycobacterium tuberculosis thymidine monophosphate kinase inhibitors. | 2003 May-Aug |
|
| 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 |
|
| Effects of single-pulse (< or = 1 ps) X-rays from laser-produced plasmas on mammalian cells. | 2004 Dec |
|
| Continuous 28-day iododeoxyuridine infusion and hyperfractionated accelerated radiotherapy for malignant glioma: a phase I clinical study. | 2004 Jul 15 |
|
| Feasibility of sodium/iodide symporter gene as a new imaging reporter gene: comparison with HSV1-tk. | 2004 Mar |
|
| Indian hedgehog: a mechanotransduction mediator in condylar cartilage. | 2004 May |
|
| [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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:36:00 GMT 2023
by
admin
on
Fri Dec 15 15:36:00 GMT 2023
|
| Record UNII |
7E78KL7PVW
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| Record Status |
Validated (UNII)
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| Record Version |
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17140-71-5
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DTXSID50169090
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28330
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| Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
