EDOXUDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H16N2O5
Molecular Weight	256.2551
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O

InChI

InChIKey=XACKNLSZYYIACO-DJLDLDEBSA-N

InChI=1S/C11H16N2O5/c1-2-6-4-13(11(17)12-10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,2-3,5H2,1H3,(H,12,16,17)/t7-,8+,9+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C11H16N2O5
Molecular Weight	256.2551
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1894930 | https://www.ncbi.nlm.nih.gov/pubmed/14743269

Edoxudine (5-ethyl-2'-deoxyuridine), an antiviral drug, has been clinically studied against the recurrent genital herpes.

Approval Year

PubMed

Title	Date	PubMed
13-Alkylpyrimidine nucleosides. Preparation and properties of 5-ethyl-2'-deoxycytidine and related nucleosides.	1974 Mar	4359544
Antiviral action and cellular toxicity of four thymidine analogues: 5-ethyl-,5-vinyl-, 5-propyl-, and 5-allyl-2'- deoxyuridine.	1976 Jul	185944
Effect of cytosine, arabinoside, iododeoxyuridine, ethyldeoxyuridine, thiocyanatodeoxyuridine, and ribavirin on tail lesion formation in mice infected with vaccinia virus.	1976 Mar	1257248
Effect of treatment with 5-ethyl-2'-deoxyuridine on herpes simplex virus encephalitis in normal and immunosuppressed mice.	1978 Nov	215081
In vitro antiherpesviral activity of 5-alkyl derivatives of 1-beta-D-arabinofuranosyluracil.	1979 Aug	485126
Relative potencies of different anti-herpes agents in the topical treatment of cutaneous herpes simplex virus infection of athymic nude mice.	1979 Nov	526011
Combination chemotherapy: interaction of 5-methoxymethyldeoxyuridine with adenine arabinoside, 5-ethyldeoxyuridine, 5-iododeoxyuridine, and phosphonoacetic acid against herpes simplex virus types 1 and 2.	1980 Apr	6249191
The 5'-monophosphates of 5-propyl- and 5-ethyl-2'-deoxyuridine do not inhibit the replication of deoxythymidine kinase deficient (TK-) mutants of herpes simplex virus.	1980 Oct 15	6254540
In vitro susceptibility of varicella-zoster virus to E-5-(2-bromovinyl)-2'-deoxyuridine and related compounds.	1982 Jan	6282207
Susceptibility of recent clinical isolates of herpes simplex virus to 5-ethyl-2'-deoxyuridine: preferential inhibition of herpes simplex virus type 2.	1983 May	6307130
Antiherpes activity of (E)-5-(2-bromovinyl)- and 5-vinyl-1-beta-D-arabinofuranosyluracil and some other 5-substituted uracil arabinosyl nucleosides in two different cell lines.	1983 Sep	6316849
5-substituted deoxyuridines--structural requirements for antiviral activity against herpes simplex virus types 1 and 2 and possible biochemical basis for relative potency.	1984 Jun	6089658
Selective in vitro and in vivo activities of 5-(2-haloalkyl)pyrimidine nucleoside analogs, particularly 5-(2-chloroethyl)-2'-deoxyuridine, against herpes simplex virus.	1985 Aug	3010841
Synthesis and antitumor and antiviral properties of 5-alkyl-2'-deoxyuridines, 3',5'-cyclic monophosphates, and neutral cyclic triesters.	1986 Apr	3959027
Activities of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine and its metabolites against herpes simplex virus types 1 and 2 in cell culture and in mice infected intracerebrally with herpes simplex virus type 2.	1986 Jan	3015003
Synthesis and antiviral activity of the carbocyclic analogues of 5-ethyl-2'-deoxyuridine and of 5-ethynyl-2'-deoxyuridine.	1986 Jan	3001308
Comparison of susceptibilities of varicella-zoster virus and herpes simplex viruses to nucleoside analogs.	1986 Mar	3013088
Incorporation and metabolism of 2'-fluoro-5-substituted arabinosyl pyrimidines and their selective inhibition of viral DNA synthesis in herpes simplex virus type 1 (HSV-1)-infected and mock-infected Vero cells.	1988 Dec 1	2852483
Synthesis and antiviral activity of phosphonoacetic and phosphonoformic acid esters of 5-bromo-2'-deoxyuridine and related pyrimidine nucleosides and acyclonucleosides.	1989 Feb	2521518
Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.	1993 Aug 20	8394933
Synthesis of new acyclic pyrimidine nucleoside analogs as potential antiviral drugs.	1994 Sep 16	7932528
Structure-activity relationship of the affinity of 5-substituted uracil nucleoside analogues for varicella-zoster virus thymidine kinase and their activity against varicella-zoster virus.	1997 Aug	9298756
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.	2001 Apr	11292644
Synthesis and antiviral activity of novel 5-(1-cyanamido-2-haloethyl) and 5-(1-hydroxy(or methoxy)-2-azidoethyl) analogues of uracil nucleosides.	2001 Oct 11	11585457
Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans.	2003 Aug 4	12898625
Design of Mycobacterium tuberculosis thymidine monophosphate kinase inhibitors.	2003 May-Aug	14565282
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.	2003 Sep 15	12941330
Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides.	2005 Dec 15	16140016
3D-QSAR studies on antitubercular thymidine monophosphate kinase inhibitors based on different alignment methods.	2006 Feb 15	16290929
Antiviral activity of 2,3'-anhydro and related pyrimidine nucleosides against hepatitis B virus.	2010 Nov 15	20863701

Patents

Sample Use Guides

In Vivo Use Guide

topical edoxudine 3.0% cream

Route of Administration: Topical

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:23:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:23:19 GMT 2023`
Record UNII	15ZQM81Y3R
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EDOXUDINE

Official Name

English

EDU

Common Name

English

URIDINE, 2'-DEOXY-5-ETHYL-

Systematic Name

English

2'-DEOXY-5-ETHYLURIDINE

Systematic Name

English

ORF-15817

Code

English

EDOXUDINE [USAN]

Common Name

English

EUDR

Common Name

English

Edoxudine [WHO-DD]

Common Name

English

5-ETHYL-3-(2'-DEOXYRIBOSYL)URACIL

Common Name

English

EDOXUDINE [MI]

Common Name

English

ORF 15817

Code

English

RWJ-15817

Code

English

RWJ 15817

Code

English

5-ETHYL-2'-DEOXYURIDINE

Systematic Name

English

NSC-758405

Code

English

edoxudine [INN]

Common Name

English

EDOXUDINE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QD06BB09