Sofosbuvir information

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: WARNINGRx-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;
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.^[3] It is taken by mouth.^[3]^[6]

Common side effects include fatigue, headache, nausea, and trouble sleeping.^[3] Side effects are generally more common in interferon-containing regimens.^[7]^: 7 Sofosbuvir may reactivate hepatitis B in those who have been previously infected.^[9] In combination with ledipasvir, daclatasvir or simeprevir, it is not recommended with amiodarone due to the risk of an abnormally slow heartbeat.^[7] Sofosbuvir is in the nucleotide analog family of medications and works by blocking the hepatitis C NS5B protein.^[6]

Sofosbuvir was discovered in 2007 and approved for medical use in the United States in 2013.^[7]^[10]^[11] It is on the World Health Organization's List of Essential Medicines.^[12]^[13]

^ Cite error: The named reference EcTimes2015 was invoked but never defined (see the help page).
^ "Sofosbuvir (Sovaldi) Use During Pregnancy". Drugs.com. 16 December 2019. Retrieved 5 February 2020.
^ ^a ^b ^c ^d "Sofosbuvir". The American Society of Health-System Pharmacists. Archived from the original on 1 December 2016. Retrieved 30 November 2016.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
^ ^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.
^ ^a ^b ^c ^d "Sovaldi- sofosbuvir tablet, film coated Sovaldi- sofosbuvir pellet". DailyMed. 27 September 2019. Retrieved 4 February 2020.
^ "Sovaldi Access- sofosbuvir tablet, film coated". DailyMed. Retrieved 26 January 2022.
^ "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.
^ "Sofosbuvir (Sovaldi) - Treatment - Hepatitis C Online". www.hepatitisc.uw.edu. Archived from the original on 23 December 2016. Retrieved 8 January 2017.
^ Gounder C (9 December 2013). "A Better Treatment for Hepatitis C". The New Yorker. Archived from the original on 20 September 2016.
^ 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.
^ 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.

[EcTimes2015-1] Cite error: The named reference EcTimes2015 was invoked but never defined (see the help page).

[Drugs.com_pregnancy-2] "Sofosbuvir (Sovaldi) Use During Pregnancy". Drugs.com. 16 December 2019. Retrieved 5 February 2020.

[AHFS2016-3] "Sofosbuvir". The American Society of Health-System Pharmacists. Archived from the original on 1 December 2016. Retrieved 30 November 2016.

[FDA-AllBoxedWarnings-4] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[5] "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.

[UKlabel-6] "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.

[Sovaldi_FDA_label-7] "Sovaldi- sofosbuvir tablet, film coated Sovaldi- sofosbuvir pellet". DailyMed. 27 September 2019. Retrieved 4 February 2020.

[8] "Sovaldi Access- sofosbuvir tablet, film coated". DailyMed. Retrieved 26 January 2022.

[FDAwarning2016-9] "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.

[UW2017-10] "Sofosbuvir (Sovaldi) - Treatment - Hepatitis C Online". www.hepatitisc.uw.edu. Archived from the original on 23 December 2016. Retrieved 8 January 2017.

[NewYorker-11] Gounder C (9 December 2013). "A Better Treatment for Hepatitis C". The New Yorker. Archived from the original on 20 September 2016.

[WHO21st-12] 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.

[WHO22nd-13] 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.

Sofosbuvir information

and 22 Related for: Sofosbuvir information

Sofosbuvir

Hepatitis C

WHO Model List of Essential Medicines

Beacon Pharmaceuticals

Ledipasvir

Annie Luetkemeyer

Velpatasvir

Coblopasvir

Hetero Drugs

Zydus Lifesciences

Gilead Sciences

Incepta Pharmaceuticals

Protide

Daclatasvir

Nucleotide

Prodrug

Amiodarone

ATC code J05

Interferon

Natco Pharma

Ribavirin

Simeprevir

Clinical data

Trade names	Sovaldi, others^[1]
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^[2]
Routes of administration	By mouth^[3]
Drug class	HCV polymerase inhibitor
ATC code	J05AP08 (WHO) J05AP51 (WHO) J05AP55 (WHO) J05AP56 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)^[5] UK: POM (Prescription only)^[6] US: WARNING^[4]Rx-only^[7]^[8] 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^Y
ChEMBL	ChEMBL1259059
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