ChemicalBook > CAS DataBase List > 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 Name
N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester
CAS No.
1234490-83-5
Chemical Name
N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester
Synonyms
INX-189;INX 08189;BMS-986094;BMS 986094 hydrate;BMS986094,BMS 986094;INX-08189 BMS 986094;N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester;L-Alanine, N-(2'-C-methyl-6-O-methyl-P-1-naphthalenyl-5'-guanylyl)-, 2,2-dimethylpropyl ester;(2S)-Neopentyl 2-(((((2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(naphthalen-1-yl)phosphoryl)amino)propanoate;(2S)-neopentyl 2-(((((2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(naphthalen-1-yloxy)phosphoryl)amino)propanoate
CBNumber
CB62604352
Molecular Formula
C30H39N6O9P
Formula Weight
658.639221
MOL File
1234490-83-5.mol
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N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester Property

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
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Tocris
Product number
6974
Product name
BMS986094
Purity
≥98%(HPLC)
Packaging
5
Price
$149
Updated
2021/12/16
Crysdot
Product number
CD21016980
Product name
INX-08189
Purity
95+%
Packaging
5mg
Price
$480
Updated
2021/12/16
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N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester Chemical Properties,Usage,Production

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

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

Raw materials

Preparation Products

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

China 25 United States 5 Global 30
Dtchem Laboratories,（Gan Su）Co.,Ltd.
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1234490-83-5, N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl esterRelated Search:


  • N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester
  • INX 08189
  • L-Alanine, N-(2'-C-methyl-6-O-methyl-P-1-naphthalenyl-5'-guanylyl)-, 2,2-dimethylpropyl ester
  • BMS-986094
  • INX-189
  • (2S)-Neopentyl 2-(((((2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(naphthalen-1-yl)phosphoryl)amino)propanoate
  • (2S)-neopentyl 2-(((((2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(naphthalen-1-yloxy)phosphoryl)amino)propanoate
  • INX-08189 BMS 986094
  • (2S)-neopentyl 2-(((((2R,3R,4R,5R)-3,4-dihydroxy-5-(2-imino-6-methoxy-2H-purin-9(3H)-yl)-4-methyltetrahydrofuran-2-yl)methoxy)(naphthalen-1-yloxy)phosphoryl)amino)propanoate
  • BMS986094,BMS 986094
  • BMS 986094 hydrate
  • 1234490-83-5
  • C30H39N6O9P