Paritaprevir

Paritaprevir
Clinical data
Trade namesViekira Pak (in combination with ombitasvir, ritonavir and dasabuvir), Technivie/Viekirax (in combination with ombitasvir and ritonavir)
Other namesVeruprevir; ABT-450
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilitywas not evaluated
Protein binding97–98.6%
MetabolismHepatic, CYP3A4 and CYP3A5
Onset of action4 to 5 hours
Elimination half-life5.5 hours
Excretionfeces (88%), urine (8,8%)
Identifiers
  • (2R,6S,12Z,13aS,14aR,16aS)-N-(Cyclopropylsulfonyl)-6-{[(5-methyl-2-pyrazinyl)carbonyl]amino}-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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC40H43N7O7S
Molar mass765.89 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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
  • Key:UAUIUKWPKRJZJV-QPLHLKROSA-N

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]: 248 

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]

References

  1. ^ Tan SL, He Y, eds. (2011). Hepatitis C: antiviral drug discovery and development. Norfolk: Caister academic press. p. 210. ISBN 9781904455783. Retrieved 28 April 2014.
  2. ^ Jensen D, Reau N, eds. (2013). Hepatitis C. New York: Oxford University Press. p. 144. ISBN 9780199844296. Retrieved 28 April 2014.
  3. ^ "Abbott Announces Phase 3 Hepatitis C Program Details". Abbott company website. Abbott Laboratories. Archived from the original on 29 April 2014. Retrieved 28 April 2014.
  4. ^ Kowdley KV, Lawitz E, Poordad F, Cohen DE, Nelson DR, Zeuzem S, et al. (January 2014). "Phase 2b trial of interferon-free therapy for hepatitis C virus genotype 1". The New England Journal of Medicine. 370 (3): 222–32. doi:10.1056/NEJMoa1306227. PMID 24428468.
  5. ^ Lange C, Sarrazin C (2013). "Hepatitis C: New Drugs". In Mauss S, Berg T, Rockstroh J, Sarrazin C (eds.). Hepatology 2013 a clinical textbook (PDF) (4th ed.). Düsseldorf: Flying Publisher. ISBN 978-3-924774-90-5. Archived from the original (PDF) on 29 April 2014. Retrieved 28 April 2014.
  6. ^ "TECHNIVIE™ (ombitasvir, paritaprevir and ritonavir) Tablets, for Oral Use. Full Prescribing Information" (PDF). AbbVie Inc., North Chicago, IL 60064. Archived from the original (PDF) on 7 August 2015. Retrieved 28 July 2015.
  7. ^ "Current and Resolved Drug Shortages and Discontinuations Reported to FDA".
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