Ledipasvir (GS5885)

For research use only, not for therapeutic use.

  • CAT Number: A000120
  • CAS Number: 1256388-51-8
  • Molecular Formula: C49H54F2N8O6
  • Molecular Weight: 889
  • Purity: ≥95%
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Ledipasvir, also known as GS-5885; is an inhibitor of the hepatitis C virus NS5A protein and is a drug for the treatment of hepatitis C that was developed by Gilead Sciences. On October 10, 2014 the FDA approved the combination product ledipasvir 90 mg/sofosbuvir 400 mg (trade name Harvoni). The ledipasvir/sofosbuvir combination is a direct-acting antiviral agent that interferes with HCV replication and can be used to treat patients with genotypes 1a or 1b without PEG-interferon or ribavirin. (http://en.wikipedia.org/wiki/Ledipasvir)


Catalog Number A000120
CAS Number 1256388-51-8
Synonyms

NA

Molecular Formula C49H54F2N8O6
Purity ≥95%
Target HCV
Solubility >44.5mg/mL in DMSO
Storage Store at -20°C
InChI InChI=1S/C49H54F2N8O6/c1-24(2)39(56-46(62)64-5)44(60)58-23-48(15-16-48)21-38(58)42-52-22-37(55-42)28-9-13-32-31-12-8-26(18-33(31)49(50,51)34(32)19-28)27-10-14-35-36(20-27)54-43(53-35)41-29-7-11-30(17-29)59(41)45(61)40(25(3)4)57-47(63)65-6/h8-10,12-14,18-2
InChIKey VRTWBAAJJOHBQU-KMWAZVGDSA-N
SMILES FC1(F)C2=C(C=CC(C3=CC(NC([C@H]4N(C([C@H](C(C)C)NC(OC)=O)=O)[C@@H]5CC[C@H]4C5)=N6)=C6C=C3)=C2)C7=CC=C(C8=CN=C([C@@H]9CC%10(CC%10)CN9C([C@H](C(C)C)NC(OC)=O)=O)N8)C=C71
Reference

</br>1: Younossi ZM, Stepanova M, Marcellin P, Afdhal N, Kowdley KV, Zeuzem S, Hunt SL. Treatment with ledipasvir and sofosbuvir improves patient-reported outcomes: Results from the Ion-1, 2 and 3 clinical trials. Hepatology. 2015 Jan 27. doi: 10.1002/hep.27724. [Epub ahead of print] PubMed PMID: 25627448.</br>2: Younossi ZM, Park H, Saab S, Ahmed A, Dieterich D, Gordon SC. Cost-effectiveness of all-oral ledipasvir/sofosbuvir regimens in patients with chronic hepatitis C virus genotype 1 infection. Aliment Pharmacol Ther. 2015 Jan 26. doi: 10.1111/apt.13081. [Epub ahead of print] PubMed PMID: 25619871.</br>3: Smith MA, Chan J, Mohammad RA. Ledipasvir-Sofosbuvir: Interferon-/Ribavirin-Free Regimen for Chronic Hepatitis C Virus Infection. Ann Pharmacother. 2014 Dec 16. pii: 1060028014563952. [Epub ahead of print] Review. PubMed PMID: 25515863.</br>4: A combination of ledipasvir and sofosbuvir (Harvoni) for hepatitis C. Med Lett Drugs Ther. 2014 Nov 10;56(1455):111-2. PubMed PMID: 25372848.</br>5: A SPECIAL MEETING REVIEW EDITION: Advances in the Treatment of Hepatitis C Virus Infection from The Liver Meeting 2013: The 64th Annual Meeting of the American Association for the Study of Liver DiseasesNovember 1-5, 2013 • Washington DCSpecial Reporting on:• Simeprevir plus Sofosbuvir with or without Ribavirin Produces High SVR Rates in Genotype 1 HCV Infection• Novel Interferon- and Ribavirin-Free Regimen Results in SVR12 Rates of Over 90% in HCV Genotype 1b Infection• Studies Confirm Efficacy of Adjunctive Simeprevir in Difficult-to-Treat HCV Genotype 1 Subpopulations• All-Oral Therapy with Sofosbuvir Plus Ribavirin Produces High SVR Rates in Patients Coinfected with HCV and HIV• Faldaprevir Combined with Pegylated Interferon and Ribavirin Demonstrates High Efficacy in DifficuIt-to-Treat HCV Infection• Once Daily Sofosbuvir/Ledipasvir Combination Elicits Rapid Decline in HCV RNAPLUS Meeting Abstract Summaries With Expert Commentary by: Ira M. Jacobson, MDWeill Cornell Medical CollegeNew York, New York. Gastroenterol Hepatol (N Y). 2014 Jan;10(1 Suppl 1):1-19. PubMed PMID: 25337060; PubMed Central PMCID: PMC4201083.</br>6: Gentile I, Borgia G. Ledipasvir/Sofosbuvir administration achieves very high rate of viral clearance in patients with HCV genotype 1 infection without cirrhosis, regardless of ribavirin co-administration or length of treatment. Evid Based Med. 2014 Dec;19(6):223-4. doi: 10.1136/ebmed-2014-110051. Epub 2014 Jul 15. PubMed PMID: 25028605.</br>7: German P, Moorehead L, Pang P, Vimal M, Mathias A. Lack of a clinically important pharmacokinetic interaction between sofosbuvir or ledipasvir and hormonal oral contraceptives norgestimate/ethinyl estradiol in HCV-uninfected female subjects. J Clin Pharmacol. 2014 Nov;54(11):1290-8. doi: 10.1002/jcph.346. Epub 2014 Jun 24. PubMed PMID: 24925712.</br>8: Afdhal N, Zeuzem S, Kwo P, Chojkier M, Gitlin N, Puoti M, Romero-Gomez M, Zarski JP, Agarwal K, Buggisch P, Foster GR, Bräu N, Buti M, Jacobson IM, Subramanian GM, Ding X, Mo H, Yang JC, Pang PS, Symonds WT, McHutchison JG, Muir AJ, Mangia A, Marcellin P; ION-1 Investigators. Ledipasvir and sofosbuvir for untreated HCV genotype 1 infection. N Engl J Med. 2014 May 15;370(20):1889-98. doi: 10.1056/NEJMoa1402454. Epub 2014 Apr 11. PubMed PMID: 24725239.</br>9: Afdhal N, Reddy KR, Nelson DR, Lawitz E, Gordon SC, Schiff E, Nahass R, Ghalib R, Gitlin N, Herring R, Lalezari J, Younes ZH, Pockros PJ, Di Bisceglie AM, Arora S, Subramanian GM, Zhu Y, Dvory-Sobol H, Yang JC, Pang PS, Symonds WT, McHutchison JG, Muir AJ, Sulkowski M, Kwo P; ION-2 Investigators. Ledipasvir and sofosbuvir for previously treated HCV genotype 1 infection. N Engl J Med. 2014 Apr 17;370(16):1483-93. doi: 10.1056/NEJMoa1316366. Epub 2014 Apr 11. PubMed PMID: 24725238.</br>10: Kowdley KV, Gordon SC, Reddy KR, Rossaro L, Bernstein DE, Lawitz E, Shiffman ML, Schiff E, Ghalib R, Ryan M, Rustgi V, Chojkier M, Herring R, Di Bisceglie AM, Pockros PJ, Subramanian GM, An D, Svarovskaia E, Hyland RH, Pang PS, Symonds WT, McHutchison JG, Muir AJ, Pound D, Fried MW; ION-3 Investigators. Ledipasvir and sofosbuvir for 8 or 12 weeks for chronic HCV without cirrhosis. N Engl J Med. 2014 May 15;370(20):1879-88. doi: 10.1056/NEJMoa1402355. Epub 2014 Apr 10. PubMed PMID: 24720702.</br>11: Gentile I, Buonomo AR, Borgia F, Castaldo G, Borgia G. Ledipasvir : a novel synthetic antiviral for the treatment of HCV infection. Expert Opin Investig Drugs. 2014 Apr;23(4):561-71. doi: 10.1517/13543784.2014.892581. Epub 2014 Mar 4. Review. PubMed PMID: 24593285.</br>12: Wyles DL, Rodriguez-Torres M, Lawitz E, Shiffman ML, Pol S, Herring RW, Massetto B, Kanwar B, Trenkle JD, Pang PS, Zhu Y, Mo H, Brainard DM, Subramanian GM, McHutchison JG, Habersetzer F, Sulkowski MS. All-oral combination of ledipasvir, vedroprevir, tegobuvir, and ribavirin in treatment-naïve patients with genotype 1 HCV infection. Hepatology. 2014 Jul;60(1):56-64. doi: 10.1002/hep.27053. Epub 2014 May 28. PubMed PMID: 24501005.</br>13: Link JO, Taylor JG, Xu L, Mitchell M, Guo H, Liu H, Kato D, Kirschberg T, Sun J, Squires N, Parrish J, Keller T, Yang ZY, Yang C, Matles M, Wang Y, Wang K, Cheng G, Tian Y, Mogalian E, Mondou E, Cornpropst M, Perry J, Desai MC. Discovery of ledipasvir (GS-5885): a potent, once-daily oral NS5A inhibitor for the treatment of hepatitis C virus infection. J Med Chem. 2014 Mar 13;57(5):2033-46. doi: 10.1021/jm401499g. Epub 2014 Jan 10. PubMed PMID: 24320933.</br>14: Gane EJ, Stedman CA, Hyland RH, Ding X, Svarovskaia E, Subramanian GM, Symonds WT, McHutchison JG, Pang PS. Efficacy of nucleotide polymerase inhibitor sofosbuvir plus the NS5A inhibitor ledipasvir or the NS5B non-nucleoside inhibitor GS-9669 against HCV genotype 1 infection. Gastroenterology. 2014 Mar;146(3):736-743.e1. doi: 10.1053/j.gastro.2013.11.007. Epub 2013 Nov 18. PubMed PMID: 24262278.</br>15: Lawitz E, Poordad FF, Pang PS, Hyland RH, Ding X, Mo H, Symonds WT, McHutchison JG, Membreno FE. Sofosbuvir and ledipasvir fixed-dose combination with and without ribavirin in treatment-naive and previously treated patients with genotype 1 hepatitis C virus infection (LONESTAR): an open-label, randomised, phase 2 trial. Lancet. 2014 Feb 8;383(9916):515-23. doi: 10.1016/S0140-6736(13)62121-2. Epub 2013 Nov 5. Erratum in: Lancet. 2014 Mar 8;383(9920):870. PubMed PMID: 24209977.</br>

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