U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of IDOXURIDINE

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

HIDE SMILES / InChI

Description
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

Curator's Comment: In rat brain

Originator

Curator's Comment: Late 1950s

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2366042
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DENDRID

Approved Use

For the treatment of keratitis caused by the virus of herpes simplex.

Launch Date

1963
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
139.03 μM × h
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Comparison of spontaneous and idoxuridine-induced micronuclei by chromosome painting.
1999 Apr 6
Hypoxia and perfusion measurements in human tumors--initial experience with pimonidazole and IUdR.
2001
Efficient in-vitro transfer of a 60-Mb mammalian artificial chromosome into murine and hamster cells using cationic lipids and dendrimers.
2001
Is there a future for cell kinetic measurements using IdUrd or BdUrd?
2001 Feb 1
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
Increased glomerular Vwf after kidney irradiation is not due to increased biosynthesis or endothelial cell proliferation.
2001 Jul
A flow cytometry technique for measuring chromosome-mediated gene transfer.
2001 Jun 1
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
[[(18)F]N-(4'-fluorobenzyl)-4-(3-bromophenyl) acetamide for imaging the sigma receptor status of tumors: comparison with [(18)F]FDG, and [(125)I]IUDR.
2001 May
Chemical modification of 5-[125I]iodo-2'-deoxyuridine toxicity in mammalian cells in vitro.
2001 May
Contact dermatitis from topical antiviral drugs.
2001 May
Synthesis and biological investigations of 5-substituted pyrimidine nucleosides coupled to a dihydropyridine/pyridinium salt redox chemical delivery system.
2001 Nov
Fluorodeoxyuridine improves imaging of human glioblastoma xenografts with radiolabeled iododeoxyuridine.
2001 Nov 1
Early detection of endogenous retroviruses in chemically induced mouse cells.
2001 Nov 5
Monte Carlo simulations and measurement of DNA damage from x-ray-triggered auger cascades in iododeoxyuridine (IUdR).
2001 Sep
Ratio of complex double strand break damage induced by 125IUdR and 123IUdR correlates with experimental in vitro cell killing effectiveness.
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
Enhanced inhibition of orthopoxvirus replication in vitro by alkoxyalkyl esters of cidofovir and cyclic cidofovir.
2002 Apr
Interventions for herpes simplex virus epithelial keratitis.
2003
Efficient one-step Suzuki arylation of unprotected halonucleosides, using water-soluble palladium catalysts.
2003 Aug 22
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
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
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
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Postherpetic neuralgia.
2003 Jun
Functional expression of a sodium dependent nucleoside transporter on rabbit cornea: Role in corneal permeation of acyclovir and idoxuridine.
2003 Mar-Apr
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
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
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
Feasibility of sodium/iodide symporter gene as a new imaging reporter gene: comparison with HSV1-tk.
2004 Mar
[The latest in herpes simplex keratitis therapy].
2004 May
Indian hedgehog: a mechanotransduction mediator in condylar cartilage.
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
[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
Patents

Sample Use Guides

1 drop (0.1% solution) every hour
Route of Administration: Topical
In Vitro Use Guide
Antiviral susceptibility of herpes simplex viruses by idoxuridine was studied in human culture cell line WI-38. Eight concentrations were tested, beginning with 1000 ug/ml and subsequent serial one-fourth dilutions. Mean MIC was 0.5 mg/ml.
Name Type Language
IDOXURIDINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
SK&F-14287
Code English
IDOXURIDINE [WHO-IP]
Common Name English
IDOXURIDINE [MART.]
Common Name English
idoxuridine [INN]
Common Name English
IDOXURIDINE [HSDB]
Common Name English
DENDRID
Brand Name English
ALLERGAN211
Code English
JODDEOXIURIDIN
Common Name English
IDOXURIDINE [USP MONOGRAPH]
Common Name English
IDOXURIDINE [USP IMPURITY]
Common Name English
SK&F 14287
Code English
IDU
Common Name English
IDOXURIDINUM [WHO-IP LATIN]
Common Name English
IDOXURIDINE [EP MONOGRAPH]
Common Name English
NSC-39661
Code English
HERPLEX
Brand Name English
STOXIL
Brand Name English
ALLERGAN-211
Code English
IODODEOXYURIDINE
Systematic Name English
IDOXURIDINE [VANDF]
Common Name English
5IUDR
Code English
IDOXURIDINE [USP-RS]
Common Name English
5-IODO-2'-DEOXYURIDINE
Systematic Name English
IDOXURIDINE [MI]
Common Name English
URIDINE, 2'-DEOXY-5-IODO-
Systematic Name English
2'-DEOXY-5-IODOURIDINE
Systematic Name English
Idoxuridine [WHO-DD]
Common Name English
5-IUDR
Code English
IDOXURIDINE [ORANGE BOOK]
Common Name English
IDOXURIDINE [JAN]
Common Name English
2'-DESOXY-5-IODOURIDINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
WHO-VATC QJ05AB02
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
NDF-RT N0000175459
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
NDF-RT N0000175459
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
WHO-ATC S01AD01
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
WHO-ATC J05AB02
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
NDF-RT N0000175466
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
WHO-ATC D06BB01
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
NDF-RT N0000175459
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
FDA ORPHAN DRUG 95696
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
WHO-VATC QS01AD01
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
WHO-VATC QD06BB01
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
Code System Code Type Description
NSC
39661
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
SMS_ID
100000083677
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
INN
1486
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IDOXURIDINE
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
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.
DAILYMED
LGP81V5245
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID2045238
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PRIMARY
FDA UNII
LGP81V5245
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PRIMARY
DRUG BANK
DB00249
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
HSDB
7479
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
PUBCHEM
5905
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
MESH
D007065
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
DRUG CENTRAL
1417
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
MERCK INDEX
m6201
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PRIMARY Merck Index
ECHA (EC/EINECS)
200-207-8
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PRIMARY
EVMPD
SUB08117MIG
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PRIMARY
RS_ITEM_NUM
1336001
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PRIMARY
CHEBI
147675
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
RXCUI
5653
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY RxNorm
CAS
54-42-2
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
NCI_THESAURUS
C563
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
ChEMBL
CHEMBL788
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY
WIKIPEDIA
IDOXURIDINE
Created by admin on Fri Dec 15 15:08:13 GMT 2023 , Edited by admin on Fri Dec 15 15:08:13 GMT 2023
PRIMARY