Sofosbuvir
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MedKoo CAT#: 314202

CAS#: 1190307-88-0

Description: 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

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Sofosbuvir
CAS# 1190307-88-0

Theoretical Analysis

MedKoo Cat#: 314202
Name: Sofosbuvir
CAS#: 1190307-88-0
Chemical Formula: C22H29FN3O9P
Exact Mass: 529.16254
Molecular Weight: 529.45253
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 Quantity
100.0mg USD 150.0 Ready to ship
200.0mg USD 250.0 Ready to ship
500.0mg USD 450.0 Ready to ship
1.0g USD 750.0 Ready to ship
2.0g USD 1250.0 Ready to ship
5.0g USD 2650.0 Ready to ship
10.0g USD 4750.0 Ready to ship
Bulk inquiry

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

Biological target: Sofosbuvir (GS-7977) is an HCV RNA replication inhibitor with an EC50 of 92 nM.
In vitro activity: On this account, this study first confirmed the increase in the phosphorylation of EGFR in response to SOF (sofosbuvir) stimulation, which in turn led to an enhanced expression of EGFR after a four-day exposure to the drug. This is consistent with previous findings showing that prolonged activation of EGFR enhances EGFR transcription through proteins downstream in the EGFR signaling pathway. Next, by introducing an EGFR inhibitor during SOF treatment, this study reversed the pro-survival outcome mediated by EGFR activation and directed cells towards apoptosis. By detecting an increase of phosphorylated EGFR in the nucleus, this study validated our proposed model: As a result of the active TP form of SOF in hepatoma cells, EGFR is activated and translocated into the nucleus, where it enhances the transcription of pro-survival genes. Reference: Cells. 2020 Apr; 9(4): 1003. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7225999/
In vivo activity: Mice with impaired innate immune response, due to the lack of type I interferon receptor (A129-/-), were infected with WT YFV (yellow fever virus) and treated with sofosbuvir at 20 mg/kg/day, again beginning one day before (pre-treatment) or after (post-treatment) infection. Results show that inoculation with 4 x 104 and 4 x 103 PFUs caused 100% mortality within one week along with massive loss in body weight (Fig 8). At these high virus inputs, pre-treatment with sofosbuvir enhanced the mean time of survival by 57%, although mortality was the final outcome for all mice (Fig 8A and 8B). At a virus dose able to cause 50% of mortality, 4 x 102 PFU, pre-treatment with sofosbuvir enhanced survival significantly (Fig 8C).Taking this last condition as reference, infectious viral titers were measured in different organs, along with serum ALT levels, liver histopathology, and white cell counts. WT YFV replicated in different anatomical compartments of the A129-/-, like peripheral blood, liver, spleen and kidney (Fig 9A–9D). In parallel to viscerotropic replication, animals rapidly progress to high virus titers in the brain (Fig 9E). Pre-treatment with sofosbuvir reduced the virus levels in the brain of the infected mice by 2-log (Fig 9E), along with leucocytosis (Fig 9F). Hepatic condition was improved in sofosbuvir-treated mice, regardless of the regimen, indicated by measuring ALT levels (Fig 9G) and liver injury (Fig 9H and 9I). Reference: PLoS Negl Trop Dis. 2019 Jan; 13(1): e0007072. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6375661/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 73.33 138.5
Ethanol 62.5 118.05
Water 25.0 47.22
PBS (pH 7.2) 0.2 0.38
DMF 20.0 37.78

Preparing Stock Solutions

The following data is based on the product molecular weight 529.45253 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.

Recalculate based on batch purity %
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: 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.
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.

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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.

Sofosbuvir

100.0mg / USD 150.0


Additional Information

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).