EPROCICLOVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H15N5O3
Molecular Weight	265.2685
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(N=CN2C[C@]3(CO)C[C@H]3CO)C(=O)N1

InChI

InChIKey=JLYSZBQNRJVPEP-KGFZYKRKSA-N

InChI=1S/C11H15N5O3/c12-10-14-8-7(9(19)15-10)13-5-16(8)3-11(4-18)1-6(11)2-17/h5-6,17-18H,1-4H2,(H3,12,14,15,19)/t6-,11-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9548818 | https://adisinsight.springer.com/drugs/800009510 | https://www.ncbi.nlm.nih.gov/pubmed/11248363 | https://www.ncbi.nlm.nih.gov/pubmed/10389656 | https://www.ncbi.nlm.nih.gov/pubmed/9687413 | https://www.ncbi.nlm.nih.gov/pubmed/9661001

Eprociclovir (A5021, 9-[[cis-1', 2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]guanine) is a nucleoside analog with antiviral activity. Antiviral activity of eprociclovir appears to depend rapid and stable accumulation of its triphosphate in infected cells and on inhibition of viral DNA polymerase by its triphosphate. Eprociclovir was shown to be a potent inhibitor of the replication of herpes simplex virus type 1, 2, 6, Epstein-Barr virus and varicella zoster virus, both in vitro and in vivo. Eprociclovir development has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
In vitro and in vivo assessment of eprociclovir as antiviral treatment against testudinid herpesvirus 3 in Hermann's tortoise (Testudo hermanni).	2019-06	30782569
Anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl] x guanine (A-5021) in vitro and in vivo.	2001-02	11248363
Evaluation of anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]- guanine (A-5021) in mice.	1999-06	10389656
Mode of action of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl) cycloprop-1'-yl]methyl]guanine (A-5021) against herpes simplex virus type 1 and type 2 and varicella-zoster virus.	1998-08	9687413
Antiherpesvirus activities of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]guanine (A-5021) in cell culture.	1998-07	9661001
Synthesis and antiviral activity of novel acyclic nucleosides: discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses.	1998-04-09	9548818

Name

Type

Language

eprociclovir [INN]

Preferred Name

English

EPROCICLOVIR

Official Name

English

A-5021

Code

English

AV-10

Code

English

9-((1,2-BIS(HYDROXYMETHYL)CYCLOPROPYL)METHYL)-1,9-DIHYDRO-, (1S-CIS)-

Systematic Name

English

6H-PURIN-6-ONE, 2-AMINO-9-(((1S,2R)-1,2-BIS(HYDROXYMETHYL)CYCLOPROPYL)METHYL)-1,9-DIHYDRO- 6H-PURIN-6-ONE, 2-AMINO-

Systematic Name

English

Code System Code Type Description

INN

10001