IDOXURIDINE

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 Search

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

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

Description
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

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2366042 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6243982	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Herpes simplex keratitis 4 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=1797	Primary		Approved 8429	DENDRID Approved Use For the treatment of keratitis caused by the virus of herpes simplex. Launch Date 1963

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

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-060333	http://www.3bsc.com/index/pro_info.php?id=99407
AHH Chemical co.,ltd	MB-01127	http://www.ahhchemical.com/product/MB-01127.html
AHH Chemical co.,ltd	MT-15852	http://www.ahhchemical.com/product/MT-15852.html
AK Scientific, Inc. (AKSCI)	I381	http://www.aksci.com/item_detail.php?cat=I381
AbMole Bioscience	M5701	http://www.abmole.com/products/idoxuridine.html
Acadechem	ACDS-064138	http://www.acadechemical.com/product/138837
Achemo Scientific Limited	AC-65310	http://www.achemo.com/search/?Keyword= 54-42-2
Achemtek	0104-021872	http://www.achemtek.com/54-42-2
Acros Organics	AC122350050	https://www.fishersci.com/shop/products/5-iodo-2-deoxyuridine-99-acros-organics-2/AC122350050
Acros Organics	AC122350250	https://www.fishersci.com/shop/products/5-iodo-2-deoxyuridine-99-acros-organics-2/AC122350250
Acros Organics	AC122350010	https://www.fishersci.com/shop/products/5-iodo-2-deoxyuridine-99-acros-organics/AC122350010
Alfa Aesar	A11542	https://www.alfa.com/en/catalog/A11542/
Alfa Chemistry	AP54422	https://reagents.alfa-chemistry.com/product/idoxuridine-cas-54-42-2-12879.html
Allbio Pharm Co., Ltd	AD03974	http://www.allbiopharm.com/product/n/AD03974
Ambinter	Amb20240644	http://www.ambinter.com/reference/20240644
Angene	AGN-PC-0OC1UC	http://www.angenechemical.com/productshow/AGN-PC-0OC1UC.html
Anward	ANW-32073	http://www.anward.com/pro_result/19475
ApexBio Technology	B1773	http://www.apexbt.com/idoxuridine.html
AstaTech, Inc.	34454	http://www.astatechinc.com/CPSResult.php?CRNO=35733
Aurum Pharmatech LLC	C-1149	http://www.Aurumpharmatech.com/Product/ProductDetails/C_1149
Avantor Inc	101095-192	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101095-192
Avantor Inc	101188-680	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101188-680
Avantor Inc	TCI0258-25G	https://us.vwr.com/store/product/9986271/5-iodo-2-deoxyuridine-idoxuridine-99-0-by-titrimetric-analysis
BLD Pharm	BD21350	http://www.bldpharm.com/products/54-42-2.html
BioChemPartner	BCP29428	http://www.biochempartner.com/54-42-2-BCP29428
BioSynth	J-009907	https://www.biosynth.com/en/products/all-products/products/J-009907.html
BioSynth	J-700180	https://www.biosynth.com/products/biochemistry/other-biochemicals/products/J-700180.html
CSNpharm	CSN12762	https://www.csnpharm.com/products/idoxuridine.html
Capot Chemical	14202	http://www.capotchem.com/en/14202.htm
Capot Chemical	PubChem14202	http://www.capotchem.com/en/14202.htm
Chem Scene	CS-2346	http://www.chemscene.com/54-42-2.html
ChemMol	30107503	http://www.chemmol.com/chemmol/30107503.html
ChemMol	97804673	http://www.chemmol.com/chemmol/97804673.html
Chemenu	CM104566	http://www.chemenu.com/products/CM104566
Chemspace	CSSB00016987667	https://chem-space.com/CSSB00016987667
DC Chemicals	DC31184	http://www.dcchemicals.com//product_show-Idoxuridine.html
Debye Scientific	DB-009133	http://www.debyesci.com/DB-009133.html
FondChemical	FDB-3203	http://www.fondchemical.com/cpshow_cid_8_pid_2479.html
Glentham Life Sciences	GP1769	http://www.glentham.com/products/product/GP1769/
LGC Standards	DRE-A14278800AL-100	https://www.lgcstandards.com/US/en/p/DRE-A14278800AL-100
LGC Standards	DRE-C14278800	https://www.lgcstandards.com/US/en/p/DRE-C14278800
LGC Standards	LGCFOR0791.00	https://www.lgcstandards.com/US/en/p/LGCFOR0791.00
LGC Standards	MM0791.00	https://www.lgcstandards.com/US/en/p/MM0791.00
Lab Network	LN00188566	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00188566
Matrix Scientific	90262	https://www.matrixscientific.com/090262.html
MedChem Express	HY-B0307	https://www.medchemexpress.com/Idoxuridine.html
MuseChem	I003999	https://www.musechem.com/product/I003999.html
OChem	5970	http://www.ocheminc.com/index.php?act=psearch&pid=134I656
Oakwood	92965	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=78139&ExtHyperLink=1
Parchem	29126	http://www.parchem.com/chemical-supplier-distributor/Idoxuridine-019126.aspx
Selleck Chemicals	S1883	http://www.selleckchem.com/products/idoxuridine.html
Sigma-Aldrich	I0050000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/i0050000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	I7125_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/i7125?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1336001_USP	https://www.sigmaaldrich.com/catalog/product/usp/1336001?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S048481	http://www.sinfoobiotech.com/product/1051879
Smolecule	S530413	http://www.smolecule.com/products/s530413
TCI (Tokyo Chemical Industry)	I0258	http://www.tcichemicals.com/eshop/en/us/commodity/I0258/index.html
THE BioTek	bt-270024	https://www.thebiotek.com/product/inhibitors/bt-270024
VladaChem	VL262525-1G	https://www.vladachem.com/product.php?products=54-42-2
abcr GmbH	AB117388	http://www.abcr.com/shop/en/AB117388
eNovation Chemicals	D481174	http://www.enovationchem.com/productDetails.asp?productID=D481174
eNovation Chemicals	D641040	https://enovationchem.com/ProductDetails.asp?ProductID=D641040
eNovation Chemicals	D911222	https://www.enovationchem.com/ProductDetails.asp?ProductID=D911222
eNovation Chemicals	Y1001627	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1001627
eNovation Chemicals	Y1044145	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1044145
iChemical	EBD3058765	http://www.ichemical.com/products/54-42-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-5585466189	https://mcule.com/MCULE-5585466189/

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	1257248
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	11761254
Fluorodeoxyuridine improves imaging of human glioblastoma xenografts with radiolabeled iododeoxyuridine.	2001 Nov 1	11691821
Ratio of complex double strand break damage induced by 125IUdR and 123IUdR correlates with experimental in vitro cell killing effectiveness.	2002	12194366
[Chromosomal abnormalities in lymphocytes from a patient with Werner's syndrome in intact culture and after treatment with halogenated analogs of thymidine].	2002	11868466
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	12173545
Induction of chromosome aberrations in unirradiated chromatin after partial irradiation of a cell nucleus.	2002 Apr	12020435
Temporal changes in the distribution of thoracic duct lymphoblasts to synovium and other tissues of rats with adjuvant-induced arthritis.	2002 Apr	11940115
Unlabelled iododeoxyuridine increases the rate of uptake of [125I]iododeoxyuridine in human xenografted glioblastomas.	2002 Apr	11914888
Enhanced inhibition of orthopoxvirus replication in vitro by alkoxyalkyl esters of cidofovir and cyclic cidofovir.	2002 Apr	11897580
HIF-1A, pimonidazole, and iododeoxyuridine to estimate hypoxia and perfusion in human head-and-neck tumors.	2002 Dec 1	12459383
Genomic variations among wildtype and mutant strains of pseudorabies virus.	2002 Jan-Mar	11942085
Metallocene-DNA: synthesis, molecular and electronic structure and DNA incorporation of C5-ferrocenylthymidine derivatives.	2002 Jul 2	12489217
Clustered sites of DNA repair synthesis during early nucleotide excision repair in ultraviolet light-irradiated quiescent human fibroblasts.	2002 Jun 10	12027458
A new bacilliform fathead minnow rhabdovirus that produces syncytia in tissue culture.	2002 May	12021863
Cell kinetic changes in human squamous cell carcinomas during radiotherapy studied using the in vivo administration of two halogenated pyrimidines.	2002 May	12008198
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	12052246
Modelling the effect of incorporated halogenated pyrimidine on radiation-induced DNA strand breaks.	2002 Nov	12456283
PET imaging drug distribution after intratumoral injection: the case for (124)I-iododeoxyuridine in malignant gliomas.	2002 Nov	12411546
Quantitative detection of (125)IdU-induced DNA double-strand breaks with gamma-H2AX antibody.	2002 Oct	12236816
Effect of 5-iodo-2'-deoxyuridine on vaccinia virus (orthopoxvirus) infections in mice.	2002 Sep	12183236
Interventions for herpes simplex virus epithelial keratitis.	2003	12917935
Study on the possibility of insulin as a carrier of IUdR for hepatocellular carcinoma-targeted therapy.	2003 Aug	12918099
Exploration of the influence of 5-iodo-2'-deoxyuridine incorporation on the structure of d[CACG(IDU)G].	2003 Aug	12876373
Efficient one-step Suzuki arylation of unprotected halonucleosides, using water-soluble palladium catalysts.	2003 Aug 22	12919046
Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans.	2003 Aug 4	12898625
Postherpetic neuralgia.	2003 Dec	15555130
[Anti-herpetic chemotherapeutic drugs].	2003 Feb	12722318
Novel agents and strategies to treat herpes simplex virus infections.	2003 Feb	12556212
Preclinical Auger and gamma radiation dosimetry for fluorodeoxyuridine-enhanced tumour proliferation scintigraphy with [123I]iododeoxyuridine.	2003 Feb	12552342
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	12525621
Protease-activated receptor (PAR)-1 and PAR-2 participate in the cell growth of alveolar capillary endothelium in primary lung adenocarcinomas.	2003 Feb 1	12548614
Inhibition of base excision repair potentiates iododeoxyuridine-induced cytotoxicity and radiosensitization.	2003 Feb 15	12591735
In vitro activity of potential anti-poxvirus agents.	2003 Jan	12615301
Biochemical and pharmacokinetic evaluation of a novel pyrimidine nucleoside nitric oxide donor as a potential anticancer/antiviral agent.	2003 Jul	12885396
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	12605988
Functional expression of a sodium dependent nucleoside transporter on rabbit cornea: Role in corneal permeation of acyclovir and idoxuridine.	2003 Mar-Apr	12815545
A simple and efficient method for synthesis of 5-substituted 2'-deoxyuridine nucleosides using metal-halogen exchange reaction of 5-iodo-2'-deoxyuridine sodium salt.	2003 May 7	12772919
Use of radiolabelled iododeoxyuridine as adjuvant treatment for experimental tumours of the liver.	2003 Oct	14515291
In vitro efficacy of ganciclovir, cidofovir, penciclovir, foscarnet, idoxuridine, and acyclovir against feline herpesvirus type-1.	2004 Apr	15077679
Topical liposomal gel of idoxuridine for the treatment of herpes simplex: pharmaceutical and clinical implications.	2004 Aug	15458233
Tracers to monitor the response to chemotherapy: in vitro screening of four radiopharmaceuticals.	2004 Aug	15453960
New tertiary constraints between the RNA components of active yeast spliceosomes: a photo-crosslinking study.	2004 Aug	15272121
Effects of single-pulse (< or = 1 ps) X-rays from laser-produced plasmas on mammalian cells.	2004 Dec	15635259
Positive interactive radiosensitisation in vitro with the combination of two nucleoside analogues, (E)-2'-deoxy-2'-(fluoromethylene) cytidine and iododeoxyuridine.	2004 Jul	15196542
Antiviral drugs in current clinical use.	2004 Jun	15125867
[The latest in herpes simplex keratitis therapy].	2004 May	15179314
Synthesis and antiviral activities of 1'-carbon-substituted 4'-thiothymidines.	2004 Oct 15	15388158
[Therapeutic effect of 125IUdR on the glioma cell line C6 in vitro and in vivo].	2004 Sep	15460416
Overexpression of p27 Kip 1, probability of cell cycle exit, and laminar destination of neocortical neurons.	2005 Sep	15647527

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:08:13 GMT 2023` Edited by `admin` on `Fri Dec 15 15:08:13 GMT 2023`
Record UNII	LGP81V5245
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IDOXURIDINE

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