CAS 1190307-88-0|Sofosbuvir
Introduction：Basic information about CAS 1190307-88-0|Sofosbuvir, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Sofosbuvir | ||
|---|---|---|---|
| CAS Number | 1190307-88-0 | Molecular Weight | 529.453 |
| Density | 1.4±0.1 g/cm3 | Boiling Point | / |
| Molecular Formula | C22H29FN3O9P | Melting Point | / |
| MSDS | / | Flash Point | / |
Names
| Name | sofosbuvir |
|---|---|
| Synonym | More Synonyms |
Sofosbuvir BiologicalActivity
| Description | Sofosbuvir (PSI-7977) is an HCV RNA replication inhibitor with an EC50 of 92 nM. |
|---|---|
| Related Catalog | Signaling Pathways >>Anti-infection >>HCVResearch Areas >>Infection |
| Target | EC50: 92±5 nM (HCV)[1] |
| In Vitro | When cathepsin A (CatA) is incubated with PSI-7977 or Sofosbuvir (PSI-7977) for 150 min, ~18-fold more PSI-352707 is formed when Sofosbuvir (PSI-7977) is the substrate compared with PSI-7976. Moreover, the catalytic efficiency for Sofosbuvir (PSI-7977) with CatA is ~30-fold higher than that for PSI-7976[1]. The genotype coverage of Sofosbuvir (PSI-7977) by using GT 1b (Con1)-, 1a (H77)-, and 2a (JFH-1)-derived replicons and GT 1b chimeric replicons containing the NS5B region from the J6 GT 2a isolate and from GT 2b and GT 3a patient isolates is evaluated, Sofosbuvir (PSI-7977) inhibits the replication of these replicons with similar EC50s (between 16 and 48 nM), and is especially active against the chimeric replicon containing the J6 NS5B (EC50=4.7 nM). Sofosbuvir (PSI-7977) inhibits clone A (GT 1b) wild-type and S282T replicons with EC90 values of 0.42 and 7.8 μM, respectively[2]. In the clone A replicon assay, Sofosbuvir (PSI-7977) produces anti-HCV activity with EC90 values 0.42 μM[3]. |
| Cell Assay | Clone A cells are seeded into T75 flasks at about 5×106 cells/flask in Dulbecco's modified Eagle's medium (DMEM) containing 100 IU/mL Penicillin/100 μg/mL streptomycin and 10% fetal bovine serum. Similarly, human primary hepatocytes are seeded in cell plating medium into T75 flasks at about 5×106 cells/flask. After overnight incubation to allow the cells to attach, cells are incubated with 50 μM PSI-7851, PSI-7976, or Sofosbuvir (PSI-7977) in fresh medium for clone A cells or in cell maintenance medium for primary hepatocytes for up to 24 h at 37°C in a 5% CO2 atmosphere. The same procedures are applied when radiolabeled PSI-7851 is used in the study except that 1×106 cells per well are seeded into a 6-well plate, and the cells are incubated with 5 μM [3H]PSI-7851. At selected times, the medium is removed, and the cell layer is washed with cold phosphate-buffered saline (PBS). After trypsinization, cells are counted and centrifuged at 1,200 rpm for 5 min. The cell pellets are suspended in 1 mL of cold 60% methanol and incubated overnight at −20°C. The samples are centrifuged at 14,000 rpm for 5 min, and the supernatants are collected and dried using a SpeedVac concentrator and stored at −20°C until they are analyzed by high performance liquid chromatography (HPLC). Residues are suspended in 100 μL of water, and 50-μL aliquots are injected into HPLC[1]. |
| References | [1]. Murakami E, et al. Mechanism of activation of PSI-7851 and its diastereoisomer PSI-7977.J Biol Chem. 2010 Nov 5;285(45):34337-47. [2]. Lam AM, et al. Genotype and subtype profiling of PSI-7977 as a nucleotide inhibitor of hepatitis C virus. Antimicrob Agents Chemother. 2012 Jun;56(6):3359-68. [3]. Sofia MJ, et al. Discovery of a β-d-2'-deoxy-2'-α-fluoro-2'-β-C-methyluridine nucleotide prodrug (PSI-7977) for the treatment of hepatitis C virus. J Med Chem. 2010 Oct 14;53(19):7202-18. [4]. Zhang X, et al. Discovery and evolution of aloperine derivatives as a new family of HCV inhibitors with novel mechanism. Eur J Med Chem. 2018 Jan 1;143:1053-1065. |
Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Molecular Formula | C22H29FN3O9P |
| Molecular Weight | 529.453 |
| Exact Mass | 529.162537 |
| PSA | 167.99000 |
| LogP | 1.62 |
| Index of Refraction | 1.573 |
| InChIKey | TTZHDVOVKQGIBA-INZZXKBOSA-N |
| SMILES | CC(C)OC(=O)C(C)NP(=O)(OCC1OC(n2ccc(=O)[nH]c2=O)C(C)(F)C1O)Oc1ccccc1 |
| Storage condition | -20°C |
Safety Information
| Hazard Codes | Xi |
|---|---|
| HS Code | 29339900 |
Synonyms
| propan-2-yl (2S)-2-[[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate |
| Sovaldi |
| Uridine, 2'-deoxy-2'-fluoro-2'-methyl-5'-O-[(S)-[[(1S)-1-methyl-2-(1-methylethoxy)-2-oxoethyl]amino]phenoxyphosphinyl]- |
| GS-7977 |
| Isopropyl (2S)-2-{[(S)-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-4-fluoro-3-hydroxy-4-methyltetrahydro-2-furanyl]methoxy}(phenoxy)phosphoryl]amino}propanoate |
| (S)-2-{(S)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}propionic acid isopropyl ester |
| Sofosbuvir |
| PSI-7977 |
