EPROCICLOVIR DIHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H15N5O3.2H2O
Molecular Weight	301.2991
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=HTUHJQCXWWQZLP-BQLITABNSA-N

InChI=1S/C11H15N5O3.2H2O/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);2*1H2/t6-,11-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C11H15N5O3
Molecular Weight	265.2685
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Synthesis and antiviral activity of novel acyclic nucleosides: discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses.	1998 Apr 9	9548818
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 Aug	9687413
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 Feb	11248363
In vitro and in vivo assessment of eprociclovir as antiviral treatment against testudinid herpesvirus 3 in Hermann's tortoise (Testudo hermanni).	2019 Jun	30782569

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:55:39 GMT 2023` Edited by `admin` on `Fri Dec 15 15:55:39 GMT 2023`
Record UNII	N157UG61BS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPROCICLOVIR DIHYDRATE

Common Name

English

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

Systematic Name

English

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

Systematic Name

English

Code System Code Type Description

CAS

635678-85-2

Created by admin on Fri Dec 15 15:55:39 GMT 2023 , Edited by admin on Fri Dec 15 15:55:39 GMT 2023

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PUBCHEM

135565564

Created by admin on Fri Dec 15 15:55:39 GMT 2023 , Edited by admin on Fri Dec 15 15:55:39 GMT 2023

PRIMARY

FDA UNII

N157UG61BS

Created by admin on Fri Dec 15 15:55:39 GMT 2023 , Edited by admin on Fri Dec 15 15:55:39 GMT 2023

PRIMARY

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