EPERVUDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H18N2O5
Molecular Weight	270.2817
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O

InChI

InChIKey=PHUUXVYXSRZACJ-IVZWLZJFSA-N

InChI=1S/C12H18N2O5/c1-6(2)7-4-14(12(18)13-11(7)17)10-3-8(16)9(5-15)19-10/h4,6,8-10,15-16H,3,5H2,1-2H3,(H,13,17,18)/t8-,9+,10+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C12H18N2O5
Molecular Weight	270.2817
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/8397468 | https://www.ncbi.nlm.nih.gov/pubmed/7885687

Epervudine (5-isopropyl-2'-deoxyuridine) is an antiviral compound. The antiviral effect of epervudine on herpes viruses (HSV-1 and HSV-2) is based on the sensitivity of virus DNA to nucleases due to epervudine incorporation into the virus DNA and the resulting change in DNA conformation. Virus selectivity is based on virus induced thymidine kinase activity and on HSV induction of polymerase enzymes catalyzing the incorporation. Epervudine (HEVIZOS) ointment is used to treat herpetic skin infections.

Originator

Approval Year

PubMed

Title	Date	PubMed
[Antiviral activity of anomeric 5-substituted 2'-deoxyuridines].	1979 Nov-Dec	524857
Differential substrate specificity of DNA polymerase beta and of a DNA polymerase induced by herpes simplex virus type 2 towards thymidine triphosphate analogues.	1984 Mar	6321635
Synthesis and antitumor and antiviral properties of 5-alkyl-2'-deoxyuridines, 3',5'-cyclic monophosphates, and neutral cyclic triesters.	1986 Apr	3959027

Patents

Sample Use Guides

In Vivo Use Guide

Epervudine (HEVIZOS) 8 mg/g ointment

Route of Administration: Topical

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:22:09 GMT 2023` Edited by `admin` on `Fri Dec 15 16:22:09 GMT 2023`
Record UNII	3G05PH9FAS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPERVUDINE

Official Name

English

.BETA.-5-ISOPROPYL-2'-DEOXYURIDINE

Common Name

English

epervudine [INN]

Common Name

English

2'-DEOXY-5-ISOPROPYLURIDINE

Systematic Name

English

HEVIZOS

Brand Name

English

Epervudine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281