AMENAMEVIR

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H26N4O5S
Molecular Weight	482.552
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC(C)=C1N(CC(=O)NC2=CC=C(C=C2)C3=NOC=N3)C(=O)C4CCS(=O)(=O)CC4

InChI

InChIKey=MNHNIVNAFBSLLX-UHFFFAOYSA-N

InChI=1S/C24H26N4O5S/c1-16-4-3-5-17(2)22(16)28(24(30)19-10-12-34(31,32)13-11-19)14-21(29)26-20-8-6-18(7-9-20)23-25-15-33-27-23/h3-9,15,19H,10-14H2,1-2H3,(H,26,29)

HIDE SMILES / InChI

Description
Sources: http://www.pmda.go.jp/files/000227731.pdf | https://www.ncbi.nlm.nih.gov/pubmed/23274658 | https://www.ncbi.nlm.nih.gov/pubmed/28681394

Amenamevir is an antiviral agent discovered by Astellas Pharma Inc. and is considered to exert anantiviral effect by inhibiting the activity of the helicase-primase complex, which is involved in DNA replication of herpes virus. It is a helicase-primase inhibitor against herpes simplex virus 1 (HSV-1), HSV-2, and varicella zoster virus. Amenamevir inhibited the in vitro replication of HSV-1 with a mean 50% effective concentration (EC(50)) of 14 ng/ml. Amenamevir was approved in Japan for the treatment of Herpes zoster.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA helicase/primase complex protein 4 Target ID: CHEMBL4380 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23274658 \| https://www.ncbi.nlm.nih.gov/pubmed/27129009	Inhibitor 8504

PubMed

Title	Date	PubMed
Efficacy of herpes virus helicase-primase inhibitor, ASP2151, for treating herpes simplex keratitis in mouse model.	2013-04	23361434
Efficacy of ASP2151, a helicase-primase inhibitor, against thymidine kinase-deficient herpes simplex virus type 2 infection in vitro and in vivo.	2012-02	22155691
ASP2151, a novel helicase-primase inhibitor, possesses antiviral activity against varicella-zoster virus and herpes simplex virus types 1 and 2.	2010-08	20534624

Sample Use Guides

In Vivo Use Guide

Herpes zoster: The usual adult dosage is 400 mg of amenamevir administered orally once daily after a meal

Route of Administration: Oral

In Vitro Use Guide

Amenamevir inhibited the DNA-dependent ATPase activity of the HSV-1 helicase-primase complex within the concentration range from 0.0001 to 3 umol/L in a concentration-dependent manner, and the 50% inhibitory concentration (IC50) was 0.078 umol/L.

Name

Type

Language

amenamevir [INN]

Preferred Name

English

AMENAMEVIR

Official Name

English

ASP2151

Code

English

Amenamevir [WHO-DD]

Common Name

English

N-(2,6-DIMETHYLPHENYL)-N-(2-((4-(1,2,4-OXADIAZOL-3-YL)PHENYL)AMINO)-2-OXOETHYL)-1,1-DIOXOTHIANE-4-CARBOXAMIDE

Systematic Name

English

ASP-2151

Code

English

AMENAMEVIR [JAN]

Common Name

English

AMENAMEVIR [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281