Paritaprevir Explained

Iupac Name:(2R,6S,12Z,13aS,14aR,16aS)-N-(Cyclopropylsulfonyl)-6--5,16-dioxo-2-(6-phenanthridinyloxy)-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[''e'']pyrrolo [1,2-''a''] [1,4]diazacyclopentadecine-14a(5H)-carboxamide
Width:285
Tradename:Viekira Pak (in combination with ombitasvir, ritonavir and dasabuvir), Technivie/Viekirax (in combination with ombitasvir and ritonavir)
Pregnancy Us:B
Licence Eu:yes
Legal Us:Rx-only
Routes Of Administration:Oral
Bioavailability:was not evaluated
Protein Bound:97–98.6%
Metabolism:Hepatic, CYP3A4 and CYP3A5
Onset:4 to 5 hours
Elimination Half-Life:5.5 hours
Excretion:feces (88%), urine (8,8%)
Cas Number:1216941-48-8
Unii:OU2YM37K86
Atc Prefix:J05
Atc Suffix:AP52
Pubchem:45110509
Chebi:85188
Chembl:3391662
Drugbank:DB09297
Chemspiderid:32700634
Kegg:D10580
Synonyms:Veruprevir; ABT-450
C:40
H:43
N:7
O:7
S:1
Smiles:Cc1cnc(cn1)C(=O)N[C@H]2CCCCC/C=C\[C@@H]3C[C@]3(NC(=O)[C@@H]4C[C@H](CN4C2=O)Oc5c6ccccc6c7ccccc7n5)C(=O)NS(=O)(=O)C8CC8
Stdinchi:1S/C40H43N7O7S/c1-24-21-42-33(22-41-24)35(48)43-32-16-6-4-2-3-5-11-25-20-40(25,39(51)46-55(52,53)27-17-18-27)45-36(49)34-19-26(23-47(34)38(32)50)54-37-30-14-8-7-12-28(30)29-13-9-10-15-31(29)44-37/h5,7-15,21-22,25-27,32,34H,2-4,6,16-20,23H2,1H3,(H,43,48)(H,45,49)(H,46,51)/b11-5-/t25-,26-,32+,34+,40-/m1/s1
Stdinchikey:UAUIUKWPKRJZJV-QPLHLKROSA-N
Jmol:None

Paritaprevir (previously known as ABT-450) is an acylsulfonamide[1] inhibitor of the NS3-4A serine protease[2] manufactured by Abbott Laboratories[3] that shows promising results as a treatment of hepatitis C. When given in combination with ritonavir and ribavirin for 12 weeks, the rate of sustained virologic response at 24 weeks after treatment has been estimated to be 95% for those with hepatitis C virus genotype 1.[4] Resistance to treatment with paritaprevir is uncommon, because it targets the binding site, but has been seen to arise due to mutations at positions 155 and 168 in NS3.[5]

Paritaprevir was a component of Viekira Pak and Technivie.[6] In May 2018, the FDA announced that Technivie and Viekira were to be discontinued. The discontinuation was voluntary and not related to the safety, quality, or efficacy of the medicine. It was estimated that both medications would be available until January 1, 2019.[7]

Notes and References

  1. Book: Hepatitis C: antiviral drug discovery and development. 2011. Caister academic press. Norfolk. 9781904455783. 210. Tan SL, He Y. 28 April 2014.
  2. Book: Hepatitis C. 2013. Oxford University Press. New York. 9780199844296. 144. Jensen D, Reau N . 28 April 2014.
  3. Web site: Abbott Announces Phase 3 Hepatitis C Program Details. Abbott company website. Abbott Laboratories. 28 April 2014.
  4. Kowdley KV, Lawitz E, Poordad F, Cohen DE, Nelson DR, Zeuzem S, Everson GT, Kwo P, Foster GR, Sulkowski MS, Xie W, Pilot-Matias T, Liossis G, Larsen L, Khatri A, Podsadecki T, Bernstein B . 6 . Phase 2b trial of interferon-free therapy for hepatitis C virus genotype 1 . The New England Journal of Medicine . 370 . 3 . 222–32 . January 2014 . 24428468 . 10.1056/NEJMoa1306227 . free .
  5. Book: Lange C, Sarrazin C . Hepatitis C: New Drugs . Mauss S, Berg T, Rockstroh J, Sarrazin C . Hepatology 2013 a clinical textbook. 2013. Flying Publisher. Düsseldorf. 4th . 28 April 2014 . dead . https://web.archive.org/web/20140429045640/http://pdf.flyingpublisher.com/Hepatology2013.pdf . 29 April 2014 . 978-3-924774-90-5 .
  6. Web site: TECHNIVIE™ (ombitasvir, paritaprevir and ritonavir) Tablets, for Oral Use. Full Prescribing Information. AbbVie Inc., North Chicago, IL 60064. 28 July 2015. https://web.archive.org/web/20150807045236/http://rxabbvie.com/pdf/technivie_pi.pdf. 7 August 2015. dead.
  7. Web site: Current and Resolved Drug Shortages and Discontinuations Reported to FDA.