BAY41-4109 racemic
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MedKoo CAT#: 530573

CAS#: 298708-79-9 (racemic)

Description: BAY41-4109 racemic is a mixture of R-isomer of BAY41-4109 and S-isomer of BAY41-4109. BAY-41-4109 is a heteroaryldihydropyrimidine (HAP) antiviral compound effective on Hepatitis B virus (HBV) capsid assembly and on preformed HBV capsids.


Chemical Structure

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BAY41-4109 racemic
CAS# 298708-79-9 (racemic)

Theoretical Analysis

MedKoo Cat#: 530573
Name: BAY41-4109 racemic
CAS#: 298708-79-9 (racemic)
Chemical Formula: C18H13ClF3N3O2
Exact Mass: 395.06
Molecular Weight: 395.766
Elemental Analysis: C, 54.63; H, 3.31; Cl, 8.96; F, 14.40; N, 10.62; O, 8.09

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 550 2 Weeks
25mg USD 950 2 Weeks
50mg USD 1650 2 Weeks
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Related CAS #: 298708-79-9 (racemic)   298708-81-3 (R-isomer)    

Synonym: BAY-41-4109; BAY41-4109; BAY 41-4109; BAY-414109; BAY414109; BAY 414109.

IUPAC/Chemical Name: Methyl 4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoropyridin-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate

InChi Key: FVNJBPMQWSIGJK-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(C1=C(C)NC(C2=NC=C(F)C=C2F)=NC1C3=CC=C(F)C=C3Cl)OC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: BAY 41-4109 is an inhibitor of human hepatitis B virus (HBV) with an IC50 of 53 nM.
In vitro activity: 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 C terminally truncated core protein was expressed and purified. Changes in hepatitis B capsid formation were assayed by dynamic light scattering and transmission electronic microscopy. Bay 41-4109 was found to be a highly selective and potent inhibitor of hepatitis B virus replication in HepG2.2.15 cells. This compound was equally effective at inhibiting HBV DNA release and the cytoplasmic HBcAg level, with 50% inhibitory concentrations of 32.6 and 132 nM, respectively. HBV DNA and HBcAg were inhibited in a dose-dependent manner, indicating that the anti-HBV mechanisms are associated with and dependent on the rate of HBcAg inhibition. Bay 41-4109 treatment disassembled the core capsids and separated them into monomers or dimers, the form in which they could be further degraded into peptides. The core protein assembled in a misdirected manner cannot function effectively. These results suggest that, based on its particular activities, Bay 41-4109 is a promising anti-HBV candidate. Reference: J Chemother. 2008 Aug;20(4):458-67. https://www.tandfonline.com/doi/abs/10.1179/joc.2008.20.4.458
In vivo activity: The antiviral effect of Bay 41-4109 was evaluated in a mouse model with humanized liver. Alb-uPA/SCID mice were transplanted with human hepatocytes and infected with HBV (hepatitis B virus). Ten days post-infection, the mice were treated with Bay 41-4109 for five days. During the 30 days of follow-up, the HBV load was evaluated by quantitative PCR. At the end of treatment, decreased HBV viremia of about 1 log(10) copies/ml was observed. By contrast, increased HBV viremia of about 0.5 log(10) copies/ml was measured in the control group. Five days after the end of treatment, a rebound of HBV viremia occurred in the treated group. Furthermore, 15 days after treatment discontinuation, a similar expression of the viral capsid was evidenced in liver biopsies. These findings demonstrate that Bay 41-4109 displayed antiviral properties against HBV in humanized Alb-uPA/SCID mice. Reference: PLoS One. 2011;6(12):e25096. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3230577/#pone.0025096-Weber1

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 89.5 226.14
Ethanol 11.0 27.79

Preparing Stock Solutions

The following data is based on the product molecular weight 395.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Billioud G, Pichoud C, Puerstinger G, Neyts J, Zoulim F. The main hepatitis B virus (HBV) mutants resistant to nucleoside analogs are susceptible in vitro to non-nucleoside inhibitors of HBV replication. Antiviral Res. 2011 Nov;92(2):271-6. doi: 10.1016/j.antiviral.2011.08.012. Epub 2011 Aug 18. PMID: 21871497. 2. Wu GY, Zheng XJ, Yin CC, Jiang D, Zhu L, Liu Y, Wei L, Wang Y, Chen HS. Inhibition of hepatitis B virus replication by Bay 41-4109 and its association with nucleocapsid disassembly. J Chemother. 2008 Aug;20(4):458-67. doi: 10.1179/joc.2008.20.4.458. PMID: 18676226. 3. Brezillon N, Brunelle MN, Massinet H, Giang E, Lamant C, DaSilva L, Berissi S, Belghiti J, Hannoun L, Puerstinger G, Wimmer E, Neyts J, Hantz O, Soussan P, Morosan S, Kremsdorf D. Antiviral activity of Bay 41-4109 on hepatitis B virus in humanized Alb-uPA/SCID mice. PLoS One. 2011;6(12):e25096. doi: 10.1371/journal.pone.0025096. Epub 2011 Dec 5. PMID: 22162746; PMCID: PMC3230577. 4. Weber O, Schlemmer KH, Hartmann E, Hagelschuer I, Paessens A, Graef E, Deres K, Goldmann S, Niewoehner U, Stoltefuss J, Haebich D, Ruebsamen-Waigmann H, Wohlfeil S. Inhibition of human hepatitis B virus (HBV) by a novel non-nucleosidic compound in a transgenic mouse model. Antiviral Res. 2002 May;54(2):69-78. doi: 10.1016/s0166-3542(01)00216-9. PMID: 12062392.
In vitro protocol: 1. Billioud G, Pichoud C, Puerstinger G, Neyts J, Zoulim F. The main hepatitis B virus (HBV) mutants resistant to nucleoside analogs are susceptible in vitro to non-nucleoside inhibitors of HBV replication. Antiviral Res. 2011 Nov;92(2):271-6. doi: 10.1016/j.antiviral.2011.08.012. Epub 2011 Aug 18. PMID: 21871497. 2. Wu GY, Zheng XJ, Yin CC, Jiang D, Zhu L, Liu Y, Wei L, Wang Y, Chen HS. Inhibition of hepatitis B virus replication by Bay 41-4109 and its association with nucleocapsid disassembly. J Chemother. 2008 Aug;20(4):458-67. doi: 10.1179/joc.2008.20.4.458. PMID: 18676226.
In vivo protocol: 1. Brezillon N, Brunelle MN, Massinet H, Giang E, Lamant C, DaSilva L, Berissi S, Belghiti J, Hannoun L, Puerstinger G, Wimmer E, Neyts J, Hantz O, Soussan P, Morosan S, Kremsdorf D. Antiviral activity of Bay 41-4109 on hepatitis B virus in humanized Alb-uPA/SCID mice. PLoS One. 2011;6(12):e25096. doi: 10.1371/journal.pone.0025096. Epub 2011 Dec 5. PMID: 22162746; PMCID: PMC3230577. 2. Weber O, Schlemmer KH, Hartmann E, Hagelschuer I, Paessens A, Graef E, Deres K, Goldmann S, Niewoehner U, Stoltefuss J, Haebich D, Ruebsamen-Waigmann H, Wohlfeil S. Inhibition of human hepatitis B virus (HBV) by a novel non-nucleosidic compound in a transgenic mouse model. Antiviral Res. 2002 May;54(2):69-78. doi: 10.1016/s0166-3542(01)00216-9. PMID: 12062392.

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1: Wu G, Liu B, Zhang Y, Li J, Arzumanyan A, Clayton MM, Schinazi RF, Wang Z, Goldmann S, Ren Q, Zhang F, Feitelson MA. Preclinical characterization of GLS4, an inhibitor of hepatitis B virus core particle assembly. Antimicrob Agents Chemother. 2013 Nov;57(11):5344-54. doi: 10.1128/AAC.01091-13. Epub 2013 Aug 19. PubMed PMID: 23959305; PubMed Central PMCID: PMC3811253.

2: Brezillon N, Brunelle MN, Massinet H, Giang E, Lamant C, DaSilva L, Berissi S, Belghiti J, Hannoun L, Puerstinger G, Wimmer E, Neyts J, Hantz O, Soussan P, Morosan S, Kremsdorf D. Antiviral activity of Bay 41-4109 on hepatitis B virus in humanized Alb-uPA/SCID mice. PLoS One. 2011;6(12):e25096. doi: 10.1371/journal.pone.0025096. Epub 2011 Dec 5. PubMed PMID: 22162746; PubMed Central PMCID: PMC3230577.

3: Billioud G, Pichoud C, Puerstinger G, Neyts J, Zoulim F. The main hepatitis B virus (HBV) mutants resistant to nucleoside analogs are susceptible in vitro to non-nucleoside inhibitors of HBV replication. Antiviral Res. 2011 Nov;92(2):271-6. doi: 10.1016/j.antiviral.2011.08.012. Epub 2011 Aug 18. PubMed PMID: 21871497.

4: Wu GY, Zheng XJ, Yin CC, Jiang D, Zhu L, Liu Y, Wei L, Wang Y, Chen HS. Inhibition of hepatitis B virus replication by Bay 41-4109 and its association with nucleocapsid disassembly. J Chemother. 2008 Aug;20(4):458-67. PubMed PMID: 18676226.

5: Pan XB, Han JC, Wei L, Peng DD, Gao Y. [Subcellular distribution and translocation of hepatitis B virus core protein in HepG2.2.15 cells]. Zhonghua Gan Zang Bing Za Zhi. 2008 Jan;16(1):29-32. Chinese. PubMed PMID: 18226340.

6: Shi C, Wu CQ, Cao AM, Sheng HZ, Yan XZ, Liao MY. NMR-spectroscopy-based metabonomic approach to the analysis of Bay41-4109, a novel anti-HBV compound, induced hepatotoxicity in rats. Toxicol Lett. 2007 Sep 28;173(3):161-7. Epub 2007 Aug 2. PubMed PMID: 17826925.

7: Stray SJ, Zlotnick A. BAY 41-4109 has multiple effects on Hepatitis B virus capsid assembly. J Mol Recognit. 2006 Nov-Dec;19(6):542-8. PubMed PMID: 17006877.

8: Hallenberger S. Antiviral therapies. J Clin Virol. 2004 Apr;30 Suppl 1:S23-5. PubMed PMID: 15062765.

9: Deres K, Schröder CH, Paessens A, Goldmann S, Hacker HJ, Weber O, Krämer T, Niewöhner U, Pleiss U, Stoltefuss J, Graef E, Koletzki D, Masantschek RN, Reimann A, Jaeger R, Gross R, Beckermann B, Schlemmer KH, Haebich D, Rübsamen-Waigmann H. Inhibition of hepatitis B virus replication by drug-induced depletion of nucleocapsids. Science. 2003 Feb 7;299(5608):893-6. PubMed PMID: 12574631.

10: Weber O, Schlemmer KH, Hartmann E, Hagelschuer I, Paessens A, Graef E, Deres K, Goldmann S, Niewoehner U, Stoltefuss J, Haebich D, Ruebsamen-Waigmann H, Wohlfeil S. Inhibition of human hepatitis B virus (HBV) by a novel non-nucleosidic compound in a transgenic mouse model. Antiviral Res. 2002 May;54(2):69-78. PubMed PMID: 12062392.