Paritaprevir

Paritaprevir

Systematic (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
Clinical data
Trade names	Viekira Pak (in combination with ombitasvir, ritonavir and dasabuvir), Technivie/Viekirax (in combination with ombitasvir and ritonavir)
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	Oral
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
Biological half-life	5.5 hours
Excretion	feces (88%), urine (8,8%)
Identifiers
CAS Number	1216941-48-8
ATC code	J05AX66 (WHO)
PubChem	CID 45110509
ChemSpider	32700634
KEGG	D10580
ChEBI	CHEBI:85188
ChEMBL	CHEMBL3391662
Synonyms	Veruprevir; ABT-450
Chemical data
Formula	C40H43N7O7S
Molar mass	765.88 g/mol
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]p. 248

Paritaprevir is a component of Viekira Pak and Technivie.^[6]

References

1. Seng-Lai Tan and Yupeng He, ed. (2011). Hepatitis C: antiviral drug discovery and development. Norfolk: Caister academic press. p. 210. ISBN 9781904455783. Retrieved 28 April 2014.
2. Donald Jensen, Nancy Reau, ed. (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. Retrieved 28 April 2014.
4. Kowdley, Kris V.; Lawitz, Eric; Poordad, Fred; Cohen, Daniel E.; Nelson, David R.; Zeuzem, Stefan; Everson, Gregory T.; Kwo, Paul; Foster, Graham R.; Sulkowski, Mark S.; Xie, Wangang; Pilot-Matias, Tami; Liossis, George; Larsen, Lois; Khatri, Amit; Podsadecki, Thomas; Bernstein, Barry (2014). "Phase 2b Trial of Interferon-free Therapy for Hepatitis C Virus Genotype 1". New England Journal of Medicine 370 (3): 222–232. doi:10.1056/NEJMoa1306227. ISSN 0028-4793.
5. Stefan Mauss; et al., eds. (2013). Hepatology 2013 a clinical textbook (PDF) (4th ed.). Düsseldorf: Flying Publisher. ISBN 978-3-924774-90-5. Retrieved 28 April 2014.
6. "TECHNIVIE™ (ombitasvir, paritaprevir and ritonavir) Tablets, for Oral Use. Full Prescribing Information" (PDF). AbbVie Inc., North Chicago, IL 60064. Retrieved 28 July 2015.