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
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
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 |
|---|---|---|
| Effect of cytosine, arabinoside, iododeoxyuridine, ethyldeoxyuridine, thiocyanatodeoxyuridine, and ribavirin on tail lesion formation in mice infected with vaccinia virus. | 1976 Mar |
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| Hypoxia and perfusion measurements in human tumors--initial experience with pimonidazole and IUdR. | 2001 |
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| Ratio of complex double strand break damage induced by 125IUdR and 123IUdR correlates with experimental in vitro cell killing effectiveness. | 2002 |
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| [Chromosomal abnormalities in lymphocytes from a patient with Werner's syndrome in intact culture and after treatment with halogenated analogs of thymidine]. | 2002 |
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| 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 |
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| Induction of chromosome aberrations in unirradiated chromatin after partial irradiation of a cell nucleus. | 2002 Apr |
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| Temporal changes in the distribution of thoracic duct lymphoblasts to synovium and other tissues of rats with adjuvant-induced arthritis. | 2002 Apr |
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| Unlabelled iododeoxyuridine increases the rate of uptake of [125I]iododeoxyuridine in human xenografted glioblastomas. | 2002 Apr |
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| Enhanced inhibition of orthopoxvirus replication in vitro by alkoxyalkyl esters of cidofovir and cyclic cidofovir. | 2002 Apr |
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| Genomic variations among wildtype and mutant strains of pseudorabies virus. | 2002 Jan-Mar |
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| Clustered sites of DNA repair synthesis during early nucleotide excision repair in ultraviolet light-irradiated quiescent human fibroblasts. | 2002 Jun 10 |
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| A new bacilliform fathead minnow rhabdovirus that produces syncytia in tissue culture. | 2002 May |
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| Cell kinetic changes in human squamous cell carcinomas during radiotherapy studied using the in vivo administration of two halogenated pyrimidines. | 2002 May |
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| 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 |
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| Quantitative detection of (125)IdU-induced DNA double-strand breaks with gamma-H2AX antibody. | 2002 Oct |
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| Effect of 5-iodo-2'-deoxyuridine on vaccinia virus (orthopoxvirus) infections in mice. | 2002 Sep |
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| Interventions for herpes simplex virus epithelial keratitis. | 2003 |
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| Efficient one-step Suzuki arylation of unprotected halonucleosides, using water-soluble palladium catalysts. | 2003 Aug 22 |
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| [Anti-herpetic chemotherapeutic drugs]. | 2003 Feb |
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| Novel agents and strategies to treat herpes simplex virus infections. | 2003 Feb |
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| Preclinical Auger and gamma radiation dosimetry for fluorodeoxyuridine-enhanced tumour proliferation scintigraphy with [123I]iododeoxyuridine. | 2003 Feb |
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| 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 |
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| Inhibition of base excision repair potentiates iododeoxyuridine-induced cytotoxicity and radiosensitization. | 2003 Feb 15 |
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| In vitro activity of potential anti-poxvirus agents. | 2003 Jan |
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| Biochemical and pharmacokinetic evaluation of a novel pyrimidine nucleoside nitric oxide donor as a potential anticancer/antiviral agent. | 2003 Jul |
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| Postherpetic neuralgia. | 2003 Jun |
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| 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 |
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| Functional expression of a sodium dependent nucleoside transporter on rabbit cornea: Role in corneal permeation of acyclovir and idoxuridine. | 2003 Mar-Apr |
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| Design of Mycobacterium tuberculosis thymidine monophosphate kinase inhibitors. | 2003 May-Aug |
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| Biliary obstruction reduces hepatic killing and phagocytic clearance of circulating microorganisms in rats. | 2003 May-Jun |
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| Use of radiolabelled iododeoxyuridine as adjuvant treatment for experimental tumours of the liver. | 2003 Oct |
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| Role of MutSalpha in the recognition of iododeoxyuridine in DNA. | 2003 Sep 1 |
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| Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides. | 2004 |
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| Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications. | 2004 Aug |
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| Tracers to monitor the response to chemotherapy: in vitro screening of four radiopharmaceuticals. | 2004 Aug |
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| New tertiary constraints between the RNA components of active yeast spliceosomes: a photo-crosslinking study. | 2004 Aug |
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| Synchrotron radiation-based experimental determination of the optimal energy for cell radiotoxicity enhancement following photoelectric effect on stable iodinated compounds. | 2004 Aug 2 |
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| Effects of single-pulse (< or = 1 ps) X-rays from laser-produced plasmas on mammalian cells. | 2004 Dec |
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| In vivo comparison of IVDU and IVFRU in HSV1-TK gene expressing tumor bearing rats. | 2004 Jan |
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| Suppression of generation and replication of acyclovir-resistant herpes simplex virus by a sensitive virus. | 2004 Jan |
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| Positive interactive radiosensitisation in vitro with the combination of two nucleoside analogues, (E)-2'-deoxy-2'-(fluoromethylene) cytidine and iododeoxyuridine. | 2004 Jul |
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| 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 |
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| Antiviral drugs in current clinical use. | 2004 Jun |
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| Antisense thymidylate synthase electrogene transfer to increase uptake of radiolabeled iododeoxyuridine in a murine model. | 2004 Mar |
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| [The latest in herpes simplex keratitis therapy]. | 2004 May |
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| Indian hedgehog: a mechanotransduction mediator in condylar cartilage. | 2004 May |
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| 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 |
|
| 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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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C1557
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WHO-VATC |
QJ05AB02
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NDF-RT |
N0000175459
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NDF-RT |
N0000175459
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WHO-ATC |
S01AD01
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WHO-ATC |
J05AB02
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NDF-RT |
N0000175466
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WHO-ATC |
D06BB01
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NCI_THESAURUS |
C281
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NDF-RT |
N0000175459
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FDA ORPHAN DRUG |
95696
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WHO-VATC |
QS01AD01
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WHO-VATC |
QD06BB01
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| Code System | Code | Type | Description | ||
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39661
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100000083677
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1486
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IDOXURIDINE
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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. | ||
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LGP81V5245
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DTXSID2045238
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LGP81V5245
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DB00249
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7479
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5905
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D007065
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1417
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m6201
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200-207-8
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SUB08117MIG
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1336001
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147675
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5653
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54-42-2
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C563
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CHEMBL788
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IDOXURIDINE
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
