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 | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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 |
|---|---|---|
| Interventions for herpes simplex virus epithelial keratitis. | 2001 |
|
| Laser cytometry of human tissues and tumors: proliferation and therapeutic applications. | 2001 |
|
| Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. | 2001 Apr |
|
| Targets for radiation-induced cell death: when DNA damage doesn't kill. | 2001 Apr |
|
| 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 |
|
| Preclinical evaluation of locoregional delivery of radiolabeled iododeoxyuridine and thymidylate synthase inhibitor in a hepatoma model. | 2001 Feb |
|
| Relative biological effectiveness of accumulated 125IdU and 125I-estrogen decays in estrogen receptor-expressing MCF-7 human breast cancer cells. | 2001 Feb |
|
| Evidence that postoperative pain is a mediator of the tumor-promoting effects of surgery in rats. | 2001 Feb 1 |
|
| In vitro effects of antiviral agents on human keratocytes. | 2001 Jan |
|
| Antizona and antisperm antibodies in women with endometriosis and/or infertility. | 2001 Jan |
|
| Laser-induced photo-cross-linking of cisplatin-modified DNA to HMG-domain proteins. | 2001 Jun 26 |
|
| 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 |
|
| Early detection of endogenous retroviruses in chemically induced mouse cells. | 2001 Nov 5 |
|
| Unlabelled iododeoxyuridine increases the rate of uptake of [125I]iododeoxyuridine in human xenografted glioblastomas. | 2002 Apr |
|
| Metallocene-DNA: synthesis, molecular and electronic structure and DNA incorporation of C5-ferrocenylthymidine derivatives. | 2002 Jul 2 |
|
| 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 |
|
| 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 |
|
| Postherpetic neuralgia. | 2003 Dec |
|
| A balanced deoxyribonucleoside mixture increased the rate of DNA incorporation of 5-[125I]Iodo-2'-deoxyuridine in glioblastoma cells. | 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 |
|
| In vitro activity of potential anti-poxvirus agents. | 2003 Jan |
|
| Postherpetic neuralgia. | 2003 Jun |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| [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 |
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:05:15 UTC 2023
by
admin
on
Wed Jul 05 23:05:15 UTC 2023
|
| Record UNII |
7E78KL7PVW
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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7E78KL7PVW
Created by
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17140-71-5
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DTXSID50169090
Created by
admin on Wed Jul 05 23:05:15 UTC 2023 , Edited by admin on Wed Jul 05 23:05:15 UTC 2023
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28330
Created by
admin on Wed Jul 05 23:05:15 UTC 2023 , Edited by admin on Wed Jul 05 23:05:15 UTC 2023
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
