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SML4173

Amenamevir

≥98% (HPLC), powder, helicase-primase complex inhibitor

Synonym(s):

2H-Thiopyran-4-carboxamide, N-(2,6-dimethylphenyl)tetrahydro-N-[2-[[4-(1,2,4-oxadiazol-3-yl)phenyl]amino]-2-oxoethyl]-, 1,1-dioxide, N-(2-((4-(1,2,4-oxadiazol-3-yl)phenyl)amino)-2-oxoethyl)-N-(2,6-dimethylphenyl)tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide, ASP 2151, ASP-2151, ASP2151

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About This Item

Empirical Formula (Hill Notation):
C24H26N4O5S
CAS Number:
841301-32-4
Molecular Weight:
482.55
MDL number:
MFCD19443709
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder
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Quality Segment

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(N(CC(NC1=CC=C(C=C1)C2=NOC=N2)=O)C3=C(C=CC=C3C)C)C4CCS(CC4)(=O)=O

Application

Amenamevir may be used in laboratory studies to investigate the mechanisms of viral replication, particularly in the context of herpes simplex virus (HSV) and varicella-zoster virus (VZV) infections. It may also be used as a model compound in the development of other antiviral agents, helping researchers understand the structure-activity relationship of helicase-primase inhibitors.

Biochem/physiol Actions

Amenamevir (ASP2151) is an orally active and potent helicase-primase complex inhibitor with equipotency against viral DNA replication of varicella-zoster virus (VZV Ellen EC50/EC90 = 47/460 nM) and herpes simplex virus (EC50/EC90 = 36/230 nM using HSV-1 (KOS) & 28/460 nM using HSV-2 (G)). This antiherpetic agent prevents the replication of these viruses. Amenamevir is much more potent (EC50 38-100 nM) than aciclovir (EC50 = 1.3-2.7 µM) against all VZV strains tested and is active against aciclovir-resistant VZV. This oxadiazolephenyl derivative is 14-times more potent than valaciclovir in a zosteriform-spread model among mice infected with HSV-1 in vivo (EC50 = 1.9 vs. 27 mg/kg, respectively, via twice daily p.o.).

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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