Paritaprevir

Paritaprevir
Clinical data
Trade names	Viekira Pak (in combination with ombitasvir, ritonavir and dasabuvir), Technivie/Viekirax (in combination with ombitasvir and ritonavir)
Other names	Veruprevir; ABT-450
License data	EU EMA: by INN;
Routes of; administration	Oral
ATC code	J05AP52 (WHO) J05AP53 (WHO);
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	was not evaluated
Protein binding	97–98.6%
Metabolism	Hepatic, CYP3A4 and CYP3A5
Onset of action	4 to 5 hours
Elimination half-life	5.5 hours
Excretion	feces (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 ;
ChEMBL	ChEMBL3391662;
Chemical and physical data
Formula	C40H43N7O7S
Molar mass	765.89 g·mol−1
3D 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. Archived from the original on 29 April 2014. 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".

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[Drugdisc-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.

[OUP-2] Jensen D, Reau N, eds. (2013). Hepatitis C. New York: Oxford University Press. p. 144. ISBN 9780199844296. Retrieved 28 April 2014.

[AbbottPR-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.

[KowdleyLawitz2014-4] 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.

[Hep2013-5] 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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