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SML2444

Sigma-Aldrich

BAY 41-4109

≥98% (HPLC)

Synonym(s):

(-)-Methyl (4R)-4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoro-2-pyridinyl)-6-methyl-1,4-dihydro-5-pyrimidinecarboxylate, (-)-Methyl 4-(2-Chloro-4-fluorophenyl)-2-(3,5-difluoro-2-pyridinyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate, BAY41-4109, Bayer 41-4109, Methyl (4R)-4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoro-2-pyridinyl)-1,4-dihydro-6-methyl-5-pyrimidinecarboxylate

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About This Item

Empirical Formula (Hill Notation):
C18H13ClF3N3O2
CAS Number:
Molecular Weight:
395.76
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

CC1=C(C(OC)=O)[C@H](C2=C(Cl)C=C(F)C=C2)N=C(C3=NC=C(F)C=C3F)N1

InChI

1S/C18H13ClF3N3O2/c1-8-14(18(26)27-2)15(11-4-3-9(20)5-12(11)19)25-17(24-8)16-13(22)6-10(21)7-23-16/h3-7,15H,1-2H3,(H,24,25)/t15-/m0/s1

InChI key

FVNJBPMQWSIGJK-HNNXBMFYSA-N

Biochem/physiol Actions

BAY41-4109 is a heteroaryldihydropyrimidine (HAP)-based capsid assembly modulator (CAM) that destabilizes hepatitis B virus (HBV) capsid assembly. BAY41-4109 inhibits HBV replication in HepG2.2.15 cultures with little host cytotoxicity (IC50 = 53 nM vs. CC50 = 7 μM in 8 days). Despite its relatively short half-life in vivo (plasma t1/2 = 5 h/dog, 2 h/rat, ≤1 h/mouse), BAY41-4109 shows greater antiviral efficacy than 3TC in Tg [HBV1.3 fsX-3′5′] mice (HBV DNA reduction = 52%/BAY vs. 36%/3TC in liver via 30 mg/kg b.i.d. p.o.; 70% vs. 30% in plasma with 15 mg BAY/kg or 30 mg/kg 3TC b.i.d. p.o., respectively) with good oral availability (F/tmax =31%/mouse, 58%/rat & dog).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Karl Deres et al.
Science (New York, N.Y.), 299(5608), 893-896 (2003-02-08)
Chronic hepatitis B virus (HBV) infection is a major cause of liver disease. Only interferon-alpha and the nucleosidic inhibitors of the viral polymerase, 3TC and adefovir, are approved for therapy. However, these therapies are limited by the side effects of
Fang Guo et al.
PLoS pathogens, 13(9), e1006658-e1006658 (2017-09-26)
Hepatitis B virus (HBV) core protein assembles viral pre-genomic (pg) RNA and DNA polymerase into nucleocapsids for reverse transcriptional DNA replication to take place. Several chemotypes of small molecules, including heteroaryldihydropyrimidines (HAPs) and sulfamoylbenzamides (SBAs), have been discovered to allosterically
O Weber et al.
Antiviral research, 54(2), 69-78 (2002-06-14)
BAY 41-4109 is a member of a class of heteroaryl-pyrimidines that was recently identified as potent inhibitors of human hepatitis B virus (HBV) replication. We have investigated the antiviral activity of BAY 41-4109 (methyl (R)-4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoro-2-pyridinyl)-6-methyl-1,4-dihydro-pyrimidine-5-carboxylate) in HBV-transgenic mice (Tg [HBV1.3
Jan Martin Berke et al.
Antiviral research, 144, 205-215 (2017-06-26)
The HBV core protein represents an attractive target for new antiviral therapies due to its multiple functions within the viral life-cycle. Here, we report the antiviral activity of the capsid assembly modulator (CAM) BAY41-4109 and two nucleos(t)ide analogues (NAs) on
Guo-Yi Wu et al.
Journal of chemotherapy (Florence, Italy), 20(4), 458-467 (2008-08-05)
The authors investigate the effects and mechanisms of the anti-hepatitis B virus (HBV) agent Bay 41-4109. HepG2.2.15 cells were used to investigate the antiviral effects of Bay 41-4109 by using real-time polymerase chain reaction (PCR), western blotting, and immunofluorescence. The

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