Sofosbuvir

Sofosbuvir, sold under the brand name Sovaldi among others, is a medication used to treat hepatitis C. It is taken by mouth.

Sofosbuvir
Clinical data
Trade namesSovaldi, others
Other namesPSI-7977; GS-7977
AHFS/Drugs.comMonograph
MedlinePlusa614014
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
Drug classHCV polymerase inhibitor
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability92%
Protein binding61–65%
MetabolismQuickly activated to triphosphate (CatA/CES1, HIST1, phosphorylation)
Elimination half-life0.4 hrs (sofosbuvir)
27 hrs (inactive metabolite GS-331007)
Excretion80% urine, 14% feces (mostly as GS-331007)
Identifiers
  • Isopropyl (2S)-2-[[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-yl]methoxy-phenoxy-phosphoryl]amino]propanoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard100.224.393
Chemical and physical data
FormulaC22H29FN3O9P
Molar mass529.458 g·mol−1
3D model (JSmol)
  • C[C@@H](C(=O)OC(C)C)N[P@](=O)(OC[C@@H]1[C@H]([C@@]([C@@H](O1)N2C=CC(=O)NC2=O)(C)F)O)OC3=CC=CC=C3
  • InChI=1S/C22H29FN3O9P/c1-13(2)33-19(29)14(3)25-36(31,35-15-8-6-5-7-9-15)32-12-16-18(28)22(4,23)20(34-16)26-11-10-17(27)24-21(26)30/h5-11,13-14,16,18,20,28H,12H2,1-4H3,(H,25,31)(H,24,27,30)/t14-,16+,18+,20+,22+,36-/m0/s1
  • Key:TTZHDVOVKQGIBA-IQWMDFIBSA-N

Common side effects include fatigue, headache, nausea, and trouble sleeping. Side effects are generally more common in interferon-containing regimens.: 7  Sofosbuvir may reactivate hepatitis B in those who have been previously infected. In combination with ledipasvir, daclatasvir or simeprevir, it is not recommended with amiodarone due to the risk of an abnormally slow heartbeat. Sofosbuvir is in the nucleotide analog family of medications and works by blocking the hepatitis C NS5B protein.

Sofosbuvir was discovered in 2007 and approved for medical use in the United States in 2013. It is on the World Health Organization's List of Essential Medicines.

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