Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H23FN5O6P |
| Molecular Weight | 431.3559 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC1=C2N=CN([C@@H]3O[C@@H]4CO[P@@](=O)(OC(C)C)O[C@H]4[C@@]3(C)F)C2=NC(N)=N1
InChI
InChIKey=PVRFQJIRERYGTQ-DSQUMVBZSA-N
InChI=1S/C16H23FN5O6P/c1-5-24-13-10-12(20-15(18)21-13)22(7-19-10)14-16(4,17)11-9(26-14)6-25-29(23,28-11)27-8(2)3/h7-9,11,14H,5-6H2,1-4H3,(H2,18,20,21)/t9-,11-,14-,16-,29+/m1/s1
| Molecular Formula | C16H23FN5O6P |
| Molecular Weight | 431.3559 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
PSI-352938 is a nucleoside derivative patented by Pharmasset, Inc. as an antiviral agent. PSI-352938 acts as a novel cyclic phosphate prodrug of β-D-2'-deoxy-2'-α-fluoro-2'-β-C-methylguanosine-5'-monophosphate with potent anti-HCV activity. PSI-352938 inhibits HCV genotype (GT) 1b replicon replication with 50% effective concentrations (EC50s) of 0.13 ± 0.076 μM, and active against GT 1a and 2a replicons and infectious viruses PSI-352938 retained full activity against replicons containing the S282T substitution, which confers resistance to certain 2'-substituted nucleoside/nucleotide analogs. In April 2013, because of hepatic toxicity, Gilead Sciences discontinued the development of PSI-352938.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hepatitis C virus nucleotide inhibitors PSI-352938 and PSI-353661 exhibit a novel mechanism of resistance requiring multiple mutations within replicon RNA. | 2011-12 |
|
| Inhibition of hepatitis C virus replicon RNA synthesis by PSI-352938, a cyclic phosphate prodrug of β-D-2'-deoxy-2'-α-fluoro-2'-β-C-methylguanosine. | 2011-06 |
Patents
| Substance Class |
Chemical
Created
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3Z30JH9QX1
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