Paritaprevir

Chemical compound

EU EMA: by INN

Routes of
administrationOralATC code

J05AP52 (WHO) J05AP53 (WHO)

US: ℞-only

Pharmacokinetic dataBioavailabilitywas not evaluatedProtein binding97–98.6%MetabolismHepatic, CYP3A4 and CYP3A5Onset of action4 to 5 hoursElimination half-life5.5 hoursExcretionfeces (88%), urine (8,8%)Identifiers

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

CAS Number

1216941-48-8

PubChem CID

45110509

DrugBank

DB09297

ChemSpider

32700634

UNII

OU2YM37K86

KEGG

D10580

ChEBI

CHEBI:85188^Y

ChEMBL

ChEMBL3391662

Chemical and physical dataFormulaC₄₀H₄₃N₇O₇SMolar mass765.89 g·mol⁻¹3D model (JSmol)

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

InChI

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

^ 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.
^ Jensen D, Reau N, eds. (2013). Hepatitis C. New York: Oxford University Press. p. 144. ISBN 9780199844296. Retrieved 28 April 2014.
^ "Abbott Announces Phase 3 Hepatitis C Program Details". Abbott company website. Abbott Laboratories. Retrieved 28 April 2014.
^ 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.
^ 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.
^ "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.
^ "Current and Resolved Drug Shortages and Discontinuations Reported to FDA".

RNA virus antivirals (primarily J05, also S01AD and D06BB)

Hepatitis C

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir^‡ Ciluprevir^§ Danoprevir^† Faldaprevir^‡ Glecaprevir Grazoprevir Narlaprevir Paritaprevir Simeprevir Sovaprevir^† Telaprevir^‡ Vaniprevir Vedroprevir^§ Voxilaprevir
NS5A inhibitors (–asvir)	Coblopasvir Daclatasvir^# Elbasvir Ledipasvir Odalasvir^† Ombitasvir Pibrentasvir Ravidasvir^† Ruzasvir^† Samatasvir^† Velpatasvir
NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Bemnifosbuvir^† Dasabuvir^# Deleobuvir^§ Filibuvir^§ GS-6620^§ IDX-184^§ Setrobuvir^§ Sofosbuvir^# Tegobuvir^§ TMC-647055^§ Radalbuvir^† Uprifosbuvir^†
Combination drugs	Elbasvir/grazoprevir Glecaprevir/pibrentasvir Ledipasvir/sofosbuvir^# Ombitasvir/paritaprevir/ritonavir^# Sofosbuvir/daclatasvir Sofosbuvir/velpatasvir^# Sofosbuvir/velpatasvir/voxilaprevir

Hepatitis D

Bulevirtide

Picornavirus

viral entry: Pleconaril^†

Anti-influenza agents

neuraminidase inhibitors/release phase (Oseltamivir^#
Zanamivir
Peramivir, Laninamivir^†)

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^# Peginterferon alfa-2b^#
3CL protease inhibitors (–trelvir)	Ensitrelvir^† Lufotrelvir Nirmatrelvir^† (+ritonavir)^† Rupintrivir Simnotrelvir (+ritonavir^†)
RNA pol inhibitors	CMX521^§ Deuremidevir^† Favipiravir Galidesivir^† GS-441524^§ Remdesivir MK-608^§ Mericitabine^† Molnupiravir NITD008^§ Ribavirin^# Taribavirin^† Triazavirin Valopicitabine^†
Multiple/Unknown/Other	EICAR^§ Merimepodib^§ Moroxydine Presatovir^†