Biology:Paritaprevir

Short description: Chemical compound

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
Pregnancy category	US: B (No risk in non-human studies)
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 Y
ChEMBL	ChEMBL3391662
Chemical and physical data
Formula	C40H43N7O7S
Molar mass	765.89 g·mol−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
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 inhibitor of the NS3-4A serine protease manufactured by Abbott Laboratories 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. 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.

Paritaprevir was a component of Viekira Pak and Technivie. 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.