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

Synonym: PSI-7977; PSI 7977; PSI7977; GS7977; GS-7977; GS 7977; Sofosbuvir; Sovaldi and Virunon.

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

Technical Data

Appearance: white solid powder

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

Certificate of Analysis: View CoA: current batch, Lot#BBC50908

QC Data: View QC data: current batch, Lot#BBC50908

Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS)

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).

Harmonized System Code: 293490

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).        

References

1: Degasperi E, Aghemo A. Sofosbuvir for the treatment of chronic hepatitis C: between current evidence and future perspectives. Hepat Med. 2014 Apr 29;6:25-33. doi: 10.2147/HMER.S44375. eCollection 2014. Review. PubMed PMID: 24822024; PubMed Central PMCID: PMC4010630.

2: Rose L, Bias TE, Mathias CB, Trooskin SB, Fong JJ. Sofosbuvir: A Nucleotide NS5B Inhibitor for the Treatment of Chronic Hepatitis C Infection. Ann Pharmacother. 2014 May 8;48(8):1019-1029. [Epub ahead of print] Review. PubMed PMID: 24811396.

3: Stedman C. Sofosbuvir, a NS5B polymerase inhibitor in the treatment of hepatitis C: a review of its clinical potential. Therap Adv Gastroenterol. 2014 May;7(3):131-40. doi: 10.1177/1756283X13515825. Review. PubMed PMID: 24790644; PubMed Central PMCID: PMC3968818.

4: Gaetano JN. Benefit-risk assessment of new and emerging treatments for hepatitis C: focus on simeprevir and sofosbuvir. Drug Healthc Patient Saf. 2014 Mar 31;6:37-45. doi: 10.2147/DHPS.S43304. eCollection 2014. Review. PubMed PMID: 24729731; PubMed Central PMCID: PMC3976205.

5: Sofosbuvir (Sovaldi) for chronic hepatitis C. Med Lett Drugs Ther. 2014 Jan 20;56(1434):5-6. Review. PubMed PMID: 24457562.

6: Asselah T, Marcellin P. Second-wave IFN-based triple therapy for HCV genotype 1 infection: simeprevir, faldaprevir and sofosbuvir. Liver Int. 2014 Feb;34 Suppl 1:60-8. doi: 10.1111/liv.12424. Review. PubMed PMID: 24373080.

7: Asselah T. Sofosbuvir for the treatment of hepatitis C virus. Expert Opin Pharmacother. 2014 Jan;15(1):121-30. doi: 10.1517/14656566.2014.857656. Epub 2013 Nov 30. Review. PubMed PMID: 24289735.

8: Mariño Z, van Bömmel F, Forns X, Berg T. New concepts of sofosbuvir-based treatment regimens in patients with hepatitis C. Gut. 2014 Feb;63(2):207-15. doi: 10.1136/gutjnl-2013-305771. Epub 2013 Nov 19. Review. PubMed PMID: 24253934.

9: Rodríguez-Torres M. Sofosbuvir (GS-7977), a pan-genotype, direct-acting antiviral for hepatitis C virus infection. Expert Rev Anti Infect Ther. 2013 Dec;11(12):1269-79. doi: 10.1586/14787210.2013.855126. Review. PubMed PMID: 24215243.

10: Gentile I, Borgia F, Buonomo AR, Castaldo G, Borgia G. A novel promising therapeutic option against hepatitis C virus: an oral nucleotide NS5B polymerase inhibitor sofosbuvir. Curr Med Chem. 2013;20(30):3733-42. Review. PubMed PMID: 23848533.