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SML2444

Sigma-Aldrich

BAY 41-4109

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C18H13ClF3N3O2
Numéro CAS:
298708-81-3
Poids moléculaire :
395.76
Numéro MDL:
MFCD11040978
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

FVNJBPMQWSIGJK-HNNXBMFYSA-N

Actions biochimiques/physiologiques

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).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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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
Nicolas Brezillon et al.
PloS one, 6(12), e25096-e25096 (2011-12-14)
Current treatments for HBV chronic carriers using interferon alpha or nucleoside analogues are not effective in all patients and may induce the emergence of HBV resistant strains. Bay 41-4109, a member of the heteroaryldihydropyrimidine family, inhibits HBV replication by destabilizing
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
Guoyi Wu et al.
Antimicrobial agents and chemotherapy, 57(11), 5344-5354 (2013-08-21)
Hepatitis B virus (HBV)-associated chronic liver diseases are treated with nucleoside analogs that target the virus polymerase. While these analogs are potent, drugs are needed to target other virus-encoded gene products to better block the virus replication cycle and chronic
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