Idoxuridine

Idoxuridine
Clinical data
Other names	Iododeoxyuridine; IUdR
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601062
Pregnancy; category	B1 (topical), B3 (ophthalmologic) [AU];
Routes of; administration	topically
ATC code	D06BB01 (WHO) J05AB02 (WHO), S01AD01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); In general: ℞ (Prescription only);
Identifiers
	IUPAC name 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione;
CAS Number	54-42-2 ;
PubChem CID	5905;
DrugBank	DB00249 ;
ChemSpider	10481938 ;
UNII	LGP81V5245;
KEGG	D00342 ;
ChEMBL	ChEMBL788 ;
NIAID ChemDB	001857;
CompTox Dashboard (EPA)	DTXSID2045238 ;
ECHA InfoCard	100.000.189
Chemical and physical data
Formula	C9H11IN2O5
Molar mass	354.100 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES I\C1=C\N(C(=O)NC1=O)C2C[C@H](O)[C@@H](CO)O2;
	InChI 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 ; Key:XQFRJNBWHJMXHO-GFCOJPQKSA-N ;
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Idoxuridine is an anti-herpesvirus antiviral drug.

It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into viral DNA replication, but the iodine atom added to the uracil component blocks base pairing. It is used only topically due to cardiotoxicity. It was synthesized by William Prusoff in the late 1950s.^[1] Initially developed as an anticancer drug, idoxuridine became the first antiviral agent in 1962.^[2]

^ Cite error: The named reference Prusoff was invoked but never defined (see the help page).
^ Wilhelmus KR (January 2015). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". The Cochrane Database of Systematic Reviews. 1 (1): CD002898. doi:10.1002/14651858.CD002898.pub5. PMC 4443501. PMID 25879115.

[Prusoff-1] Cite error: The named reference Prusoff was invoked but never defined (see the help page).

[Wilhelmus-2] Wilhelmus KR (January 2015). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". The Cochrane Database of Systematic Reviews. 1 (1): CD002898. doi:10.1002/14651858.CD002898.pub5. PMC 4443501. PMID 25879115.

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