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1190307-88-0
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???(??):
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Sofosbuvir
???(??):
Suofeibuwei;(S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-Methyltetrahydrofuran-2-yl)Methoxy)(phenoxy)phosphoryl)aMino)propanoate;Sophy Bouvet;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;propan-2-yl (2S)-2-[[[(2R,3R,4R,5S)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate;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;GS-7977;PSI 7977;Sofosbubir;sofosbuvir
CBNumber:
CB02604350
???:
C22H29FN3O9P
??? ??:
529.45
MOL ??:
1190307-88-0.mol

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122-124°C
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1.41
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Hygroscopic, -20°C Freezer, Under inert atmosphere
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DMSO(?? ???), ???(?? ???)
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?? ?? (pKa)
9.39±0.10(Predicted)
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InChIKey
TTZHDVOVKQGIBA-YBSJRAAASA-N
SMILES
C(OC(C)C)(=O)[C@@H](N[P@@](OC[C@@H]1[C@@H](O)[C@](F)(C)[C@H](N2C(=O)NC(=O)C=C2)O1)(OC1=CC=CC=C1)=O)C
CAS ??????
1190307-88-0
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  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
HS ?? 29339900
?? ?? ??? 1190307-88-0(Hazardous Substances Data)
????(GHS): GHS hazard pictogramsGHS hazard pictograms
?? ?: Warning
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?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H373 ??? ?? ?? ???? ??(??, ??? ?? ??? ?? ??? ??)? ??? ??? ? ?? ?? ???? ?? - ?? ?? ?? 2 ?? P260, P314, P501
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P260 ??·?·??·???·??·...·????? ???? ???.
P314 ???? ??? ???? ??·??? ????.
P501 ...? ??? / ??? ?? ???.
NFPA 704
0
2 0

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Sofosbuvir is a drug used for the treatment of hepatitis C. It is recommended to be used in combination with other drugs (such as velpatasvir) for the first-line treatment for HCV genotypes 1, 2, 3, 4, 5, and 6. It takes effect through acting as a nucleotide analog inhibitor, being capable of specially inhibiting the HCV NS5B (non-structural protein 5B) RNA-dependent RNA polymerase.

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PSI-7977 is a prodrug that is metabolized to the active antiviral agent 2'-deoxy-2'-α-fluoro-β-C-methyluridine-5'-monophosphate and is currently being investigated in phase 3 clinical trials for the t reatment of hepatitis C. Studies have profiled PSI-7977 as a nucleotide inhibitor of hepatitis C virus, exerting selective inhibitory effects towards HCV NS5B polymerase.

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ChEBI: A nucleotide conjugate that is used in combination with ledipasvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection.

Clinical Use

In December 2013, sofosbuvir (also known as GS-7977 and PSI-7977) was approved in the United States for the treatment of hepatitis C virus (HCV) infection as a component of a combination antiviral treatment regimen. Sofosbuvir was discovered from an effort to enhance the activity of the parent nucleoside by bypassing rate-limiting monophosphorylation with a prodrug that would liberate the intactmonophosphate in the liver, where it would then be converted by cellular kinases to the active triphosphate species. In addition, the prodrug was designed to be amenable to oral delivery. In the initial synthesis of sofosbuvir, the iso-propyl ester of (L)-alanine was coupled with phenyl dichlorophosphate to provide a diastereomeric intermediate that was coupled with the uridine nucleoside. The diastereomeric mixture (GS-9851) was shown to produce high levels of triphosphate in vitro in primary hepatocytes and in the livers of rats, dogs, and monkeys after oral dosing. The individual diastereomers were obtained by chromatography or by crystallization. The diastereomer with the Sp configuration at the phosphorous center (sofosbuvir) was found to be >10-fold more potent in an HCV replicon assay than the corresponding Rp diastereomer (EC90s of 0.42 and 7.5 μM, respectively).

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N-[(S)-(2,3,4,5,6-?????????)???????]-L-???1-???????? N-[(S)-(4-??????)???????]-L-???1-???????? 2'-???-2'-????-2'-C-?????

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