Sofosbuvir | PSI-7977 | GS7977 | Sovaldi | Virunon | CAS#1190307-88-0 | nucleotide analog inhibitor

MedKoo Cat#: 314202 | Name: Sofosbuvir

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sofosbuvir, also known as PSI-7977 and GS7977 (brand names Sovaldi and Virunon), is a drug used for hepatitis C virus (HCV) infection, with a high cure rate. It inhibits the RNA polymerase that the hepatitis C virus uses to replicate its RNA. It was discovered at Pharmasset and developed by Gilead Sciences. Sofosbuvir is a component of the first all-oral, interferon-free regimen approved for treating chronic Hepatitis C. In 2013, the FDA approved sofosbuvir in combination with ribavirin (RBV) for oral dual therapy of HCV genotypes 2 and 3, and for triple therapy with injected pegylated interferon (pegIFN) and RBV for treatment-naive patients with HCV genotypes 1 and 4.

Chemical Structure

Sofosbuvir

CAS#1190307-88-0

Theoretical Analysis

MedKoo Cat#: 314202

Name: Sofosbuvir

CAS#: 1190307-88-0

Chemical Formula: C22H29FN3O9P

Exact Mass: 529.1625

Molecular Weight: 529.45

Elemental Analysis: C, 49.91; H, 5.52; F, 3.59; N, 7.94; O, 27.20; P, 5.85

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to ship
200mg	USD 150.00	Ready to ship
500mg	USD 250.00	Ready to ship
1g	USD 450.00	Ready to ship
2g	USD 750.00	Ready to ship
5g	USD 1,450.00	Ready to ship
10g	USD 2,250.00	Ready to ship

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Related CAS #

No Data

Synonym

PSI-7977; PSI 7977; PSI7977; GS7977; GS-7977; GS 7977; Sofosbuvir; Sovaldi; Virunon; Vosevi; Hepcinat; Hepcvir; Resof;

IUPAC/Chemical Name

(2S)-isopropyl 2-(((((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

InChi Key

TTZHDVOVKQGIBA-IAAJYNJHSA-N

InChi Code

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

SMILES Code

C[C@H](NP(OC1=CC=CC=C1)(OC[C@H]2O[C@@H](N(C(N3)=O)C=CC3=O)[C@](C)(F)[C@@H]2O)=O)C(OC(C)C)=O

Appearance

white solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Sofosbuvir treatment regimens last 12 weeks for genotypes 1, 2 and 4, compared to 24 weeks for treatment of genotype 3. The label further states that sofosbuvir in combination with ribavirin may be considered for patients infected with genotype 1 who are interferon-ineligible. Sofosbuvir will cost $84,000 for 12 weeks of treatment and $168,000 for the 24 weeks, which some patient advocates have criticized as unaffordable. Interferon-free therapy for treatment of hepatitis C eliminates the substantial side-effects associated with use of interferon. Up to half of hepatitis C patients cannot tolerate the use of interferon. (http://en.wikipedia.org/wiki/Sofosbuvir).

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#BBC50908

QC Data

View QC data: current batch, Lot#BBC50908

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Sofosbuvir is an HCV RNA replication inhibitor with an EC50 of 92 nM.

In vitro activity:

This study suggests that sofosbuvir may have an impact on pathological processes in the liver via the induction of EGFR signaling. Sofosbuvir treatment enhanced translocation of EGFR into the nucleus and transactivation of factors associated with cell cycle progression, B-MYB and Cyclin D1. There were other pathways, especially the MAPK pathway, also activated during sofosbuvir treatment. Reference: Cells. 2020 Apr; 9(4): 1003. https://pubmed.ncbi.nlm.nih.gov/32316635/

In vivo activity:

Sofosbuvir may represent a novel therapeutic option for yellow fever treatment. Sofosbuvir protected yellow fever virus-infected neonatal Swiss mice and adult type I interferon receptor knockout mice (A129-/-) from mortality and weight loss. Reference: PLoS Negl Trop Dis. 2019 Jan; 13(1): e0007072. https://pubmed.ncbi.nlm.nih.gov/30699122/

	Solvent	mg/mL	mM
Solubility
	DMSO	73.3	138.50
	Ethanol	62.5	118.05
	Water	25.0	47.22
	PBS (pH 7.2)	0.2	0.38
	DMF	20.0	37.78

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 529.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Boccuto A, Dragoni F, Picarazzi F, Lai A, Della Ventura C, Veo C, Giammarino F, Saladini F, Zehender G, Zazzi M, Mori M, Vicenti I. Sofosbuvir Selects for Drug-Resistant Amino Acid Variants in the Zika Virus RNA-Dependent RNA-Polymerase Complex In Vitro. Int J Mol Sci. 2021 Mar 6;22(5):2670. doi: 10.3390/ijms22052670. PMID: 33800884; PMCID: PMC7962015. 2. Bojkova D, Westhaus S, Costa R, Timmer L, Funkenberg N, Korencak M, Streeck H, Vondran F, Broering R, Heinrichs S, Lang KS, Ciesek S. Sofosbuvir Activates EGFR-Dependent Pathways in Hepatoma Cells with Implications for Liver-Related Pathological Processes. Cells. 2020 Apr 17;9(4):1003. doi: 10.3390/cells9041003. PMID: 32316635; PMCID: PMC7225999. 3. de Freitas CS, Higa LM, Sacramento CQ, Ferreira AC, Reis PA, Delvecchio R, Monteiro FL, Barbosa-Lima G, James Westgarth H, Vieira YR, Mattos M, Rocha N, Hoelz LVB, Leme RPP, Bastos MM, Rodrigues GOL, Lopes CEM, Queiroz-Junior CM, Lima CX, Costa VV, Teixeira MM, Bozza FA, Bozza PT, Boechat N, Tanuri A, Souza TML. Yellow fever virus is susceptible to sofosbuvir both in vitro and in vivo. PLoS Negl Trop Dis. 2019 Jan 30;13(1):e0007072. doi: 10.1371/journal.pntd.0007072. PMID: 30699122; PMCID: PMC6375661. 4. Ferreira AC, Zaverucha-do-Valle C, Reis PA, Barbosa-Lima G, Vieira YR, Mattos M, Silva PP, Sacramento C, de Castro Faria Neto HC, Campanati L, Tanuri A, Brüning K, Bozza FA, Bozza PT, Souza TML. Sofosbuvir protects Zika virus-infected mice from mortality, preventing short- and long-term sequelae. Sci Rep. 2017 Aug 25;7(1):9409. doi: 10.1038/s41598-017-09797-8. PMID: 28842610; PMCID: PMC5573375.

In vitro protocol:

In vivo protocol:

1. de Freitas CS, Higa LM, Sacramento CQ, Ferreira AC, Reis PA, Delvecchio R, Monteiro FL, Barbosa-Lima G, James Westgarth H, Vieira YR, Mattos M, Rocha N, Hoelz LVB, Leme RPP, Bastos MM, Rodrigues GOL, Lopes CEM, Queiroz-Junior CM, Lima CX, Costa VV, Teixeira MM, Bozza FA, Bozza PT, Boechat N, Tanuri A, Souza TML. Yellow fever virus is susceptible to sofosbuvir both in vitro and in vivo. PLoS Negl Trop Dis. 2019 Jan 30;13(1):e0007072. doi: 10.1371/journal.pntd.0007072. PMID: 30699122; PMCID: PMC6375661. 2. Ferreira AC, Zaverucha-do-Valle C, Reis PA, Barbosa-Lima G, Vieira YR, Mattos M, Silva PP, Sacramento C, de Castro Faria Neto HC, Campanati L, Tanuri A, Brüning K, Bozza FA, Bozza PT, Souza TML. Sofosbuvir protects Zika virus-infected mice from mortality, preventing short- and long-term sequelae. Sci Rep. 2017 Aug 25;7(1):9409. doi: 10.1038/s41598-017-09797-8. PMID: 28842610; PMCID: PMC5573375.

1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548823/ PubMed PMID: 31644130. 2: Childs-Kean LM, Brumwell NA, Lodl EF. Profile of sofosbuvir/velpatasvir/voxilaprevir in the treatment of hepatitis C. Infect Drug Resist. 2019 Jul 23;12:2259-2268. doi: 10.2147/IDR.S171338. eCollection 2019. Review. PubMed PMID: 31413603; PubMed Central PMCID: PMC6662169. 3: Sofosbuvir/velpatasvir/voxilaprevir for hepatitis C. Aust Prescr. 2019 Jun;42(3):108-109. doi: 10.18773/austprescr.2019.033. Epub 2019 Apr 24. Review. PubMed PMID: 31363313; PubMed Central PMCID: PMC6594850. 4: Catalli L, Martens SK, Terrault NA, Reeves JD. Novel NS5B Resistance-Associated Substitution Emerges Under Failing Sofosbuvir/Ledipasvir Therapy. Clin Liver Dis (Hoboken). 2019 Mar 29;13(3):74-78. doi: 10.1002/cld.768. eCollection 2019 Mar. Review. PubMed PMID: 30988941; PubMed Central PMCID: PMC6446458. 5: Mucenic M, Brandão ABM, Marroni CA, Fleck Junior AM, Zanotelli ML, Leipnitz I, Meine MH, Kiss G, Martini J, Schlindwein ES, Costabeber AM, Sacco FKR, Rossato G, Cantisani GPC. Sofosbuvir, ribavirin and pegylated interferon for a daclatasvir-resistent genotype 3 hepatitis C virus: case report and review. Rev Inst Med Trop Sao Paulo. 2019 Feb 14;61:e12. doi: 10.1590/S1678-9946201961012. Review. PubMed PMID: 30785566; PubMed Central PMCID: PMC6376924. 6: Bourlière M, Pietri O, Castellani P, Oules V, Adhoute X. Sofosbuvir, velpatasvir and voxilaprevir: a new triple combination for hepatitis C virus treatment. One pill fits all? Is it the end of the road? Therap Adv Gastroenterol. 2018 Dec 2;11:1756284818812358. doi: 10.1177/1756284818812358. eCollection 2018. Review. PubMed PMID: 30574189; PubMed Central PMCID: PMC6295690. 7: Pharmacoeconomic Review Report: Sofosbuvir/Velpatasvir/Voxilaprevir (Vosevi): (Gilead Sciences Canada, Inc.): Indication: Hepatitis C infection genotype 1 to 6 [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Feb. Available from http://www.ncbi.nlm.nih.gov/books/NBK534109/ PubMed PMID: 30480922. 8: Clinical Review Report: Sofosbuvir / Velpatasvir / Voxilaprevir (Vosevi): (Gilead Sciences Canada, Inc.): Indication: Hepatitis C infection genotype 1 to 6 [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Feb. Available from http://www.ncbi.nlm.nih.gov/books/NBK534032/ PubMed PMID: 30475545. 9: CADTH Canadian Drug Expert Committee Recommendation: Sofosbuvir/Velpatasvir/Voxilaprevir (Vosevi — Gilead Sciences Canada, Inc.): Indication: Chronic hepatitis C virus infection [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Jan. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK533004/ PubMed PMID: 30427626. 10: Zignego AL, Monti M, Gragnani L. Sofosbuvir/Velpatasvir for the treatment of Hepatitis C Virus infection. Acta Biomed. 2018 Oct 8;89(3):321-331. doi: 10.23750/abm.v89i3.7718. Review. PubMed PMID: 30333452; PubMed Central PMCID: PMC6502110. 11: Pearlman BL, Hinds AE. Review article: novel antivirals for hepatitis C-sofosbuvir/velpatasvir/voxilaprevir, glecaprevir/pibrentasvir. Aliment Pharmacol Ther. 2018 Nov;48(9):914-923. doi: 10.1111/apt.14977. Epub 2018 Oct 4. Review. PubMed PMID: 30288771. 12: Yang CHT, Goel A, Ahmed A. Clinical utility of ledipasvir/sofosbuvir in the treatment of adolescents and children with hepatitis C. Adolesc Health Med Ther. 2018 Jul 30;9:103-110. doi: 10.2147/AHMT.S147896. eCollection 2018. Review. PubMed PMID: 30104913; PubMed Central PMCID: PMC6071628. 13: Rivero-Juarez A, Brieva T, Frias M, Rivero A. Pharmacodynamic and pharmacokinetic evaluation of the combination of daclatasvir/sofosbuvir/ribavirin in the treatment of chronic hepatitis C. Expert Opin Drug Metab Toxicol. 2018 Sep;14(9):901-910. doi: 10.1080/17425255.2018.1506765. Epub 2018 Aug 2. Review. PubMed PMID: 30058394. 14: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500824/ PubMed PMID: 29999883. 15: Summers BB. Sofosbuvir, velpatasvir and voxilaprevir combination therapy for treating patients with hepatitis C virus infection. Drugs Today (Barc). 2018 Apr;54(4):255-268. doi: 10.1358/dot.2018.54.4.2788017. Review. PubMed PMID: 29869647. 16: German P, Mathias A, Brainard DM, Kearney BP. Drug-Drug Interaction Profile of the Fixed-Dose Combination Tablet Regimen Ledipasvir/Sofosbuvir. Clin Pharmacokinet. 2018 Nov;57(11):1369-1383. doi: 10.1007/s40262-018-0654-5. Review. PubMed PMID: 29644537. 17: Heo YA, Deeks ED. Sofosbuvir/Velpatasvir/Voxilaprevir: A Review in Chronic Hepatitis C. Drugs. 2018 Apr;78(5):577-587. doi: 10.1007/s40265-018-0895-5. Review. PubMed PMID: 29546556. 18: Dashti-Khavidaki S, Khalili H, Nasiri-Toosi M. Potential nephrotoxicity of sofosbuvir-based treatment in patients infected with hepatitis C virus: a review on incidence, type and risk factors. Expert Rev Clin Pharmacol. 2018 May;11(5):525-529. doi: 10.1080/17512433.2018.1451327. Epub 2018 Mar 14. Review. PubMed PMID: 29533117. 19: Scott LJ. Ledipasvir/Sofosbuvir: A Review in Chronic Hepatitis C. Drugs. 2018 Feb;78(2):245-256. doi: 10.1007/s40265-018-0864-z. Review. PubMed PMID: 29380288. 20: Chahine EB, Kelley D, Childs-Kean LM. Sofosbuvir/Velpatasvir/Voxilaprevir: A Pan-Genotypic Direct-Acting Antiviral Combination for Hepatitis C. Ann Pharmacother. 2018 Apr;52(4):352-363. doi: 10.1177/1060028017741508. Epub 2017 Nov 8. Review. PubMed PMID: 29115151.