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PSI-352938

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Category Hepatitis C Virus (HCV)
CAS 1231747-17-3
Description PSI-352938 is an inhibitor of hepatitis C virus (HCV) nucleotide.
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Product Information

Synonyms PSI-938; (4aR,6R,7R,7aR)-6-(2-Amino-6-ethoxy-9H-purin-9-yl)-7-fluoro-2-isopropoxy-7-methyltetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine 2-oxide; 6-Ethoxy-9-[(4aR,6R,7R,7aR)-7-fluoro-2-isopropoxy-7-methyl-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-9H-purin-2-amine; Guanosine, 2'-deoxy-6-O-ethyl-2'-fluoro-2'-methyl-, cyclic 3',5'-(1-methylethyl phosphate), (2'R)-; (2'R)-2'-Deoxy-6-O-ethyl-2'-fluoro-2'-methylguanosine cyclic 3',5'-(1-methylethyl phosphate); GS 0938; PSI 352938; PSI352938; PSI 938; PSI938
IUPAC Name 9-[(4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-propan-2-yloxy-4,4a,6,7a-tetrahydrofuro[3,2-d][1,3,2]dioxaphosphinin-6-yl]-6-ethoxypurin-2-amine
Molecular Weight 431.36
Molecular Formula C16H23FN5O6P
Canonical SMILES CCOC1=NC(=NC2=C1N=CN2C3C(C4C(O3)COP(=O)(O4)OC(C)C)(C)F)N
InChI 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
InChIKey PVRFQJIRERYGTQ-UYISCHNFSA-N
Boiling Point 622.5±65.0°C at 760 mmHg
Purity ≥95%
Density 1.70±0.1 g/cm3
Solubility Soluble in DMSO
Appearance Solid powder
Storage Store at -20°C
Complexity 663
Exact Mass 431.13699863
In Vitro PSI-352938 (PSI-938) and PSI-353661 inhibit HCV genotype (GT) 1b replicon replication with 50% effective concentrations (EC50s) of 0.13±0.076 μM and 3.0±1.4 nM, respectively, and are similarly active against GT 1a and 2a replicons and infectious viruses. Metabolism of PSI-352938 and PSI-353661 generates the same 5'-triphosphate metabolite, PSI-352666, which is similarly active against NS5B polymerases from GT 1 to 4. PSI-352938 (PSI-938) is a novel cyclic phosphate prodrug of β-D-2'-deoxy-2'-α-fluoro-2'-β-C-methylguanosine 5'-monophosphate that has potent activity against HCV. PSI-352938 (PSI-938) has similar activity against genotype 1a, 1b, and 2a replicons, with EC50s ranging from 0.13 to 0.20 μM and EC90 values ranging from 0.35 to 0.74 μM. PSI-352938 (PSI-938) also effectively inhibits HCV replication in the infectious virus assays: the EC50 and EC90 values are 0.28±0.083 μM and 0.63±0.018 μM, respectively, against the H77 infectious virus and 0.39±0.31 μM and 1.16±0.64 μM, respectively, against the JFH-1 infectious virus. In contrast, PSI-352938 is not active against HBV or HIV up to the highest concentration tested (EC50>100 μM).
PSA 143.38000
Target HCV
XLogP3-AA 0.7

Description of First Aid Measures

Eye contact

Remove any contact lenses, locate eye-wash station, and flush eyes immediately with large amounts of water. Separate eyelids with fingers to ensure adequate flushing. Promptly call a physician.

Skin contact

Rinse skin thoroughly with large amounts of water. Remove contaminated clothing and shoes and call a physician.

Inhalation

Immediately relocate self or casualty to fresh air. If breathing is difficult, give cardiopulmonary resuscitation (CPR). Avoid mouth-to-mouth resuscitation.

Ingestion

Wash out mouth with water; Do NOT induce vomiting; call a physician.

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