paritaprevir

{{Short description|Chemical compound}}

{{Infobox drug

| drug_name =

| IUPAC_name = (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

| image = File:Paritaprevir structure 2.svg

| width = 285

| alt =

| caption =

| tradename = Viekira Pak (in combination with ombitasvir, ritonavir and dasabuvir), Technivie/Viekirax (in combination with ombitasvir and ritonavir)

| Drugs.com =

| MedlinePlus =

| pregnancy_AU =

| pregnancy_US = B

| pregnancy_category =

| licence_EU = yes

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Rx-only

| legal_status =

| 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_Ref = {{fdacite|correct|FDA}}

| UNII = OU2YM37K86

| ATCvet =

| ATC_prefix = J05

| ATC_suffix = AP52

| ATC_supplemental ={{ATC|J05|AP53}}

| PubChem = 45110509

| ChEBI_Ref = {{ebicite|correct|EBI}}

| 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{{cite book|title=Hepatitis C: antiviral drug discovery and development|year=2011|publisher=Caister academic press|location=Norfolk|isbn=9781904455783|pages=210|url=https://books.google.com/books?id=pd0O9SXEBhoC&pg=PA210| veditors = Tan SL, He Y|access-date=28 April 2014}} inhibitor of the NS3-4A serine protease{{cite book|title=Hepatitis C|year=2013|publisher=Oxford University Press|location=New York|isbn=9780199844296|page=144|url=https://books.google.com/books?id=yrNeD8d8wB8C&pg=PA144| veditors = Jensen D, Reau N |access-date=28 April 2014}} manufactured by Abbott Laboratories{{cite web|title=Abbott Announces Phase 3 Hepatitis C Program Details|url=http://www.abbott.com/news-media/press-releases/abbott-announces-phase-3-hepatitis-c-program-details.htm|work=Abbott company website|publisher=Abbott Laboratories|access-date=28 April 2014|archive-date=29 April 2014|archive-url=https://web.archive.org/web/20140429061906/http://www.abbott.com/news-media/press-releases/abbott-announces-phase-3-hepatitis-c-program-details.htm|url-status=dead}} 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.{{cite journal | vauthors = 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 | display-authors = 6 | title = Phase 2b trial of interferon-free therapy for hepatitis C virus genotype 1 | journal = The New England Journal of Medicine | volume = 370 | issue = 3 | pages = 222–32 | date = January 2014 | pmid = 24428468 | doi = 10.1056/NEJMoa1306227 | doi-access =free }} 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.{{cite book | vauthors = Lange C, Sarrazin C | chapter = Hepatitis C: New Drugs | veditors = Mauss S, Berg T, Rockstroh J, Sarrazin C |title=Hepatology 2013 a clinical textbook|year=2013|publisher=Flying Publisher|location=Düsseldorf|url=http://pdf.flyingpublisher.com/Hepatology2013.pdf|edition=4th |access-date=28 April 2014 |url-status=dead |archive-url= https://web.archive.org/web/20140429045640/http://pdf.flyingpublisher.com/Hepatology2013.pdf |archive-date=29 April 2014 | isbn = 978-3-924774-90-5 }}{{rp|248}}

Paritaprevir was a component of Viekira Pak and Technivie.{{cite web|title=TECHNIVIE™ (ombitasvir, paritaprevir and ritonavir) Tablets, for Oral Use. Full Prescribing Information|url=http://rxabbvie.com/pdf/technivie_pi.pdf|publisher=AbbVie Inc., North Chicago, IL 60064|access-date=28 July 2015|archive-url=https://web.archive.org/web/20150807045236/http://rxabbvie.com/pdf/technivie_pi.pdf|archive-date=7 August 2015|url-status=dead}} 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.{{cite web|title=Current and Resolved Drug Shortages and Discontinuations Reported to FDA|url=https://www.accessdata.fda.gov/scripts/drugshortages/dsp_ActiveIngredientDetails.cfm?AI=Ombitasvir%3B+Paritaprevir%3B+Ritonavir+%28Technivie%29+Tablets&st=d&tab=tabs-2}}