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

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

Idoxuridine is an antiviral agent use in keratitis caused by herpes simplex virus. As a prescription drug it comes as a 0.1% ophthalmic solution/drops (Herplex and Dendrid). The first studies of the compound for treatment of human herpes simplex started in early 1960s. Being a structural analog of thymidine idoxuridine inhibits viral DNA replication by substituting thymidine. The effect of idoxuridine results in the inability of the virus to reproduce and/or infect tissues. Idoxuridine also blocks viral thymidine kinase as its substrate analog.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282	Binding Agent 1,076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Herpes simplex keratitis 4	Primary		Approved 8,583	DENDRID

AUC

AUC

Value	Dose	Co-administered	Analyte	Population
139.03 μM × h	4538 mg/m² 1 times / day multiple, intraperitoneal		IDOXURIDINE plasma	Homo sapiens

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-060333	http://www.3bsc.com/index/pro_info.php?id=99407
abcr GmbH	AB117388	http://www.abcr.com/shop/en/AB117388
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

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PubMed

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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
Preclinical evaluation of locoregional delivery of radiolabeled iododeoxyuridine and thymidylate synthase inhibitor in a hepatoma model.	2001 Feb	11216535
Is there a future for cell kinetic measurements using IdUrd or BdUrd?	2001 Feb 1	11173147
Increased glomerular Vwf after kidney irradiation is not due to increased biosynthesis or endothelial cell proliferation.	2001 Jul	11418069
A flow cytometry technique for measuring chromosome-mediated gene transfer.	2001 Jun 1	11378859

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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.

Show entries

Name

Type

Language

DENDRID

Preferred Name

English

IDOXURIDINE

Official Name

English

SK&F-14287

Code

English

IDOXURIDINE [WHO-IP]

Common Name

English

IDOXURIDINE [MART.]

Common Name

English

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Classification Tree

Code System

Code

Antimetabolite

NCI_THESAURUS

C1557

Nucleosides and nucleotides excl. reverse transcriptase inhibitors

WHO-VATC

QJ05AB02

Analogs/Derivatives

NDF-RT

N0000175459

Nucleosides

NDF-RT

N0000175459

Antivirals

WHO-ATC

S01AD01

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Code System

Code

Type

Description

NSC

39661

PRIMARY

SMS_ID

100000083677

PRIMARY

INN

1486

PRIMARY

WHO INTERNATIONAL PHARMACOPEIA

IDOXURIDINE

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

PRIMARY

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ACTIVE MOIETY


					LGP81V5245

IDOXURIDINE

PRODRUG (METABOLITE ACTIVE)


					3HX21A3SQF

ROPIDOXURIDINE

SALT/SOLVATE (PARENT)


					7E78KL7PVW

IDOXURIDINE MONOHYDRATE