Sofosbuvir

Sofosbuvir
Clinical data
Trade namesSovaldi, others[1]
Other namesPSI-7977; GS-7977
AHFS/Drugs.comMonograph
MedlinePlusa614014
License data
Pregnancy
category
Routes of
administration		By mouth[3]
Drug classHCV polymerase inhibitor
ATC code
Legal status
Legal status
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
IUPAC name
  • 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
CompTox Dashboard (EPA)
ECHA InfoCard100.224.393
Chemical and physical data
FormulaC22H29FN3O9P
Molar mass529.458 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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

Sofosbuvir, sold under the brand name Sovaldi among others, is a medication used to treat hepatitis C.[3] It is taken by mouth.[3][5]

Common side effects include fatigue, headache, nausea, and trouble sleeping.[3] Side effects are generally more common in interferon-containing regimens.[6]: 7  Sofosbuvir may reactivate hepatitis B in those who have been previously infected.[8] In combination with ledipasvir, daclatasvir or simeprevir, it is not recommended with amiodarone due to the risk of an abnormally slow heartbeat.[6] Sofosbuvir is in the nucleotide analog family of medications and works by blocking the hepatitis C NS5B protein.[5]

Sofosbuvir was discovered in 2007 and approved for medical use in the United States in 2013.[6][9][10] It is on the World Health Organization's List of Essential Medicines.[11][12]

  1. ^ Cite error: The named reference EcTimes2015 was invoked but never defined (see the help page).
  2. ^ "Sofosbuvir (Sovaldi) Use During Pregnancy". Drugs.com. 16 December 2019. Retrieved 5 February 2020.
  3. ^ a b c d "Sofosbuvir". The American Society of Health-System Pharmacists. Archived from the original on 1 December 2016. Retrieved 30 November 2016.
  4. ^ "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
  5. ^ a b c "Sovaldi 400 mg film coated tablets - Summary of Product Characteristics". UK Electronic Medicines Compendium. September 2016. Archived from the original on 10 November 2016. Retrieved 10 November 2016.
  6. ^ a b c d "Sovaldi- sofosbuvir tablet, film coated Sovaldi- sofosbuvir pellet". DailyMed. 27 September 2019. Retrieved 4 February 2020.
  7. ^ "Sovaldi Access- sofosbuvir tablet, film coated". DailyMed. Retrieved 26 January 2022.
  8. ^ "Direct-Acting Antivirals for Hepatitis C: Drug Safety Communication - Risk of Hepatitis B Reactivating". FDA. 4 October 2016. Archived from the original on 6 October 2016. Retrieved 6 October 2016.
  9. ^ "Sofosbuvir (Sovaldi) - Treatment - Hepatitis C Online". www.hepatitisc.uw.edu. Archived from the original on 23 December 2016. Retrieved 8 January 2017.
  10. ^ Gounder C (9 December 2013). "A Better Treatment for Hepatitis C". The New Yorker. Archived from the original on 20 September 2016.
  11. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  12. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
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