Paritaprevir

Paritaprevir
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
ATC code	J05AX66 (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
Biological 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
Synonyms	Veruprevir; ABT-450
CAS Number	1216941-48-8
PubChem (CID)	45110509
ChemSpider	32700634
KEGG	D10580
ChEBI	CHEBI:85188^Y
ChEMBL	CHEMBL3391662
Chemical and physical data
Formula	C₄₀H₄₃N₇O₇S
Molar mass	765.88 g/mol
3D model (Jmol)	Interactive image
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

↑ Seng-Lai Tan; Yupeng He, eds. (2011). Hepatitis C: antiviral drug discovery and development. Norfolk: Caister academic press. p. 210. ISBN 9781904455783. Retrieved 28 April 2014.
↑ Donald Jensen; Nancy Reau, 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, 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.
↑ 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.
↑ "TECHNIVIE™ (ombitasvir, paritaprevir and ritonavir) Tablets, for Oral Use. Full Prescribing Information" (PDF). AbbVie Inc., North Chicago, IL 60064. Retrieved 28 July 2015.

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

Hepatitis C

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir Faldaprevir^‡ Grazoprevir Paritaprevir Simeprevir Telaprevir

NS5A inhibitors (–asvir)	Daclatasvir Elbasvir Ledipasvir MK-3682 MK-8408 Odalasvir^† Ombitasvir Ravidasvir^† Samatasvir^† Velpatasvir

NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Dasabuvir Deleobuvir^§ Filibuvir^§ Setrobuvir^§ Sofosbuvir Radalbuvir^†

Combination drugs	Elbasvir/grazoprevir Ledipasvir/sofosbuvir Ombitasvir/paritaprevir/ritonavir Sofosbuvir/daclatasvir Velpatasvir/sofosbuvir

Picornavirus

viral entry: Pleconaril^†

Anti-influenza agents

Umifenovir

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

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^#

Multiple/unknown	BCX4430^† Favipiravir GS-5734^† Mericitabine^† MK-608^§ NITD008^§ Moroxydine Ribavirin^#/Taribavirin^† Triazavirin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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