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SML2995

Sigma-Aldrich

Enviroxime

≥98% (HPLC)

Synonym(s):

(E)-(2-Amino-1-(isopropylsulfonyl)-1H-benzo[d]imidazol-6-yl)(phenyl)methanone oxime, (E)-6-[(Hydroxyimino)phenylmethyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine, (E)-LY 122771-72, (E)-LY-122771-72, (E)-LY122771-72, (E)-Viroxime, 6-[(E)-(Hydroxyimino)phenylmethyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine, EvirX, LY 122772, LY-122772, LY122772

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About This Item

Empirical Formula (Hill Notation):
C17H18N4O3S
CAS Number:
72301-79-2
Molecular Weight:
358.41
MDL number:
MFCD00866954
UNSPSC Code:
41121800
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

, White to very dark grey

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

NC1=NC(C=CC(/C(C2=CC=CC=C2)=N/O)=C3)=C3N1S(C(C)C)(=O)=O

Biochem/physiol Actions

Enviroxime (LY 122772) is a selective phosphatidylinositol 4-kinase type IIIβ (PI4KB, PI4KIIIβ) inhibitor (IC50 = 60 nM/PI4KB vs. 1.917 µM/PI4KA) with antiviral potency against enteroviruses, including rhinovirus (RV plaque reduction IC50 ≤40 ng/mL; HeLa), poliovirus (PV), coxsackievirus (CV). PI4KB is a host factor essential for enterovirus replication, mutations in viral 3A protein that recruits PI4KB to the replication sites result in enviroxime resistance. Enviroxime is also reported to impede PI4K-independent hepatitis C (HCV) replication at least partially by an inhibitory effect on PI3Ks.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sequence determinants of 3A-mediated resistance to enviroxime in rhinoviruses and enteroviruses
Journal of Virology, 70, 4854-4857 (1996)
Eradication of persistent coxsackievirus B infection from a pancreatic cell line with clinically used antiviral drugs
Journal of Clinical Virology, 128, 104334-104334 (2020)
PI4KIII inhibitor enviroxime impedes the replication of the hepatitis C virus by inhibiting PI3 kinases
The Journal of Antimicrobial Chemotherapy, 73, 3375-3384 (2018)
Coxsackievirus mutants that can bypass host factor PI4KIII? and the need for high levels of PI4P lipids for replication
Cell Research, 22, 1576-1592 (2012)
Synthesis of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine. Inhibitors of rhinovirus multiplication
Journal of Medicinal Chemistry, 23, 368-372 (1980)
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