Sofosbuvir

Sofosbuvir
Clinical data
Trade names	Sovaldi, others
Other names	PSI-7977; GS-7977
AHFS/Drugs.com	Monograph
MedlinePlus	a614014
License data	EU EMA: by INN; US DailyMed: Sofosbuvir; US FDA: Sofosbuvir;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
Drug class	HCV polymerase inhibitor
ATC code	J05AP08 (WHO) J05AP51 (WHO) J05AP55 (WHO) J05AP56 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	92%
Protein binding	61–65%
Metabolism	Quickly activated to triphosphate (CatA/CES1, HIST1, phosphorylation)
Elimination half-life	0.4 hrs (sofosbuvir); 27 hrs (inactive metabolite GS-331007)
Excretion	80% 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	1190307-88-0;
PubChem CID	45375808;
IUPHAR/BPS	7368;
DrugBank	DB08934;
ChemSpider	26286922;
UNII	WJ6CA3ZU8B;
KEGG	D10366;
ChEBI	CHEBI:85083 ;
ChEMBL	ChEMBL1259059;
CompTox Dashboard (EPA)	DTXSID701027632 ;
ECHA InfoCard	100.224.393
Chemical and physical data
Formula	C22H29FN3O9P
Molar mass	529.458 g·mol−1
3D model (JSmol)	Interactive image;
	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. It is taken by mouth.

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.