Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H17FN5O13P3 |
| Molecular Weight | 539.1981 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]1(F)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N2C=NC3=C2N=C(N)NC3=O
InChI
InChIKey=GFEXCNGIPRYQFE-GITKWUPZSA-N
InChI=1S/C11H17FN5O13P3/c1-11(12)6(18)4(2-27-32(23,24)30-33(25,26)29-31(20,21)22)28-9(11)17-3-14-5-7(17)15-10(13)16-8(5)19/h3-4,6,9,18H,2H2,1H3,(H,23,24)(H,25,26)(H2,20,21,22)(H3,13,15,16,19)/t4-,6-,9-,11-/m1/s1
| Molecular Formula | C11H17FN5O13P3 |
| Molecular Weight | 539.1981 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| 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 Dec |
|
| 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 Jun |
Patents
| Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 14:34:19 GMT 2023
by
admin
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Sat Dec 16 14:34:19 GMT 2023
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| Record UNII |
IR49Q7E87C
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| Record Status |
Validated (UNII)
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| Record Version |
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1261253-79-5
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