ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Alanine derivatives N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester

N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester

Product NameN-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester
CAS1234490-83-5
MFC30H39N6O9P
MW658.639221
EINECS
MOL File1234490-83-5.mol

Chemical Properties

Boiling point	848.7±75.0 °C(Predicted)
Density	1.47
storage temp.	Store at -20°C
solubility	Soluble in DMSO
pka	13.01±0.70(Predicted)
form	Solid
color	White to off-white
InChIKey	YFXGICNMLCGLHJ-RSKRLRQZSA-N
SMILES	[P](=O)(N[C@@H](C)C(=O)OCC(C)(C)C)(OC[C@H]3O[C@H]([C@@]([C@@H]3O)(O)C)[n]4c5[nH][c](nc(c5nc4)OC)=N)Oc1c2c(ccc1)cccc2

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Uses

BMS-986094 (INX-08189) is a potent inhibitor of hepatitis C virus (HCV) replication, with an EC50 of 35 nM at 24 h in Huh-7 cells. BMS-986094 is a phosphoramidate proagent of 6-O-methyl-2’-C-methyl guanosine. BMS-986094 can be used for the research of chronic HCV infection[1][2].

Biological Activity

BMS-986094 is an orally available prodrug of nucleotide analogue 2′-C-methylguanosine th at potently inhibits Hepatitis C virus (HCV) replication. It is a guanosine nucleotide inhibitor of HCV RNA-dependent RNA polymerase NS5b.

in vivo

BMS-986094 (3-300 mg/kg; p.o.) converts to 2′-C-Me-GTP after oral administration, and 2’-C-MeG in the plasma is proportional to the production of 2’-C-MeGTP in the liver^[1].
BMS-986094 (25 mg/kg; p.o.) is efficiently extracts from the portal circulation by the liver following oral administration in cynomolgus monkeys^[1].
BMS-986094 (15 or 30 mg/kg/d; p.o. for 3 weeks) administers cynomolgus monkeys, the nucleoside metabolite M2 was the major plasma analyte, and INX-09114 was the highest drug-related species in the heart and kidney^[3].

Animal Model:	Male Sprague-Dawley rats^[1]
Dosage:	3, 5, 10, 25 mg/kg
Administration:	A single p.o. administration
Result:	At doses of ≥5 mg/kg, the concentrations of 2′-C-MeGTP in the liver exceeded the EC₉₀ soon after dosing and remained at or above this level for 72 h.

storage

Store at -20°C

References

[1] Vernachio JH, et, al. INX-08189, a phosphoramidate prodrug of 6-O-methyl-2'-C-methyl guanosine, is a potent inhibitor of hepatitis C virus replication with excellent pharmacokinetic and pharmacodynamic properties. Antimicrob Agents Chemother. 2011 May; 55(5): 1843-51. DOI:10.1128/AAC.01335-10
[2] McGuigan C, et, al. Design, synthesis and evaluation of a novel double pro-drug: INX-08189. A new clinical candidate for hepatitis C virus. Bioorg Med Chem Lett. 2010 Aug 15; 20(16): 4850-4. DOI:10.1016/j.bmcl.2010.06.094
[3] Li W, et, al. In Vitro Metabolite Formation in Human Hepatocytes and Cardiomyocytes and Metabolism and Tissue Distribution in Monkeys of the 2'-C-Methylguanosine Prodrug BMS-986094. Int J Toxicol. 2017 Jan 1; 1091581816683642. DOI:10.1177/1091581816683642

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