Bay 41-4109 less active enantiomer

Category	Hepatitis B Virus (HBV)
CAS	476617-51-3
Description	Bay 41-4109 less active enantiomer exhibits less activity than Bay 41-4109 that is a novel class of drugs and inhibits hepatitis B virus (HBV) capsid formation and replication.

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Product Information

Synonyms	methyl (4R)-4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoropyridin-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate; BAY 41-4109; methyl-(R)-4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoro-2-pyridinyl)-6-methyl-1,4-dihydro-pyrimidine-5-carboxylate
IUPAC Name	methyl (4S)-4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoropyridin-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate
Molecular Weight	395.76
Molecular Formula	C18H13ClF3N3O2
Canonical SMILES	CC1=C(C(N=C(N1)C2=C(C=C(C=N2)F)F)C3=C(C=C(C=C3)F)Cl)C(=O)OC
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
InChIKey	FVNJBPMQWSIGJK-HNNXBMFYSA-N
Boiling Point	475.3±45.0 ℃ at 760 Torr
Purity	≥98% (HPLC)
Density	1.46±0.1 g/cm3
Solubility	DMSO: ≥ 37 mg/mL
Appearance	Solid powder
Storage	Store in a cool and dry place (or refer to the Certificate of Analysis).
Animal Admin	The HBV transgenic mice were used in this study. The compound (BAY 41-4109) is formulated into a suspension in 0.5% Tylose and administered orally to mice twice/day for 28 days. Liver is removed and immediately frozen for subsequent analysis. Blood is obtained by a cardiac puncture of an anesthetized animal.
Assay	Cellular metabolism is assessed by MTT colorimetry. HepG2.2.15 cells are seeded in 96-well plates at a density of 2×103 cells per well. After 8 days of treatment with different concentrations of each antiviral compound, add 20 μl LMTT solution (5 g/L) to each well and incubate at 37 °C for 4 h. Record absorbance values at 490 nm by using an ELISA reader. Calculate the MTT value using the curve regression equation.
Complexity	645
Exact Mass	395.0648388
In Vitro	BAY 41-4109 accelerates and misleads capsid assembly in vitro. BAY 41-4109 is equally effective in inhibiting HBV DNA release and cytoplasmic HBcAg levels, with IC50s of HepG2.2.15 cells being 32.6 and 132 nM, respectively.
In Vivo	BAY 41-4109 dose-dependently reduces viral DNA in the liver and plasma, the potency of which is comparable to 3TC. BAY 41-4109 reduces the hepatitis B virus core antigen (HBcAg) in the liver of HBV transgenic mice. Pharmacokinetic studies in mice have shown rapid absorption in rats and dogs, with a bioavailability of 30%, and a dose-proportional plasma concentration of approximately 60%.
Target	IC50: 53 nM (HBV, Bay 41-4109)
XLogP3-AA	3.1