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Details

Stereochemistry ABSOLUTE
Molecular Formula C40H43N7O7S
Molecular Weight 765.877
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PARITAPREVIR

SMILES

[H][C@@]12C[C@]1(NC(=O)[C@]3([H])C[C@H](CN3C(=O)[C@H](CCCCCC=C2)NC(=O)C4=CN=C(C)C=N4)OC5=NC6=C(C=CC=C6)C7=C5C=CC=C7)C(=O)NS(=O)(=O)C8CC8

InChI

InChIKey=UAUIUKWPKRJZJV-QPLHLKROSA-N
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

HIDE SMILES / InChI
Molecular Formula C40H43N7O7S
Molecular Weight 765.877
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Paritaprevir is a potent inhibitor of the NS3/4A protease that rapidly and consistently suppresses HCV. Paritaprevir is metabolized by the Cytochrome P450 isoform 3A (CYP3A); therefore, ritonavir was used concurrently to increase plasma concentrations and to prolong the half-life of this agent allowing for once-daily dosing. Several antiviral regimens combining paritaprevir with other agents have shown impressive results, tolerable side effects, and importantly, provided support of ‘all-oral’ interferon-free regimens against HCV. Paritaprevir monotherapy is discontinued now but paritaprevir is used as a component of Viekira Pak and Technivie for the treatment of patients with genotype 1 chronic hepatitis C virus (HCV) infection.

Originator

Approval Year

2014
494
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
Inhibitor
8297
 0.18 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
TECHNIVIE

Approved Use

TECHNIVIE is a fixed-dose combination of ombitasvir, a hepatitis C virus NS5A inhibitor, paritaprevir, a hepatitis C virus NS3/4A protease inhibitor, and ritonavir, a CYP3A inhibitor and is indicated in combination with ribavirin for the treatment of patients with genotype 4 chronic hepatitis C virus (HCV) infection without cirrhosis or with compensated cirrhosis.

Launch Date

2015
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
262 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: [NO STEREO] OMBITASVIR
[NO STEREO] OMBITASVIR
 [NO STEREO] PARITAPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2220 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: [NO STEREO] OMBITASVIR
[NO STEREO] OMBITASVIR
 [NO STEREO] PARITAPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: [NO STEREO] OMBITASVIR
[NO STEREO] OMBITASVIR
 [NO STEREO] PARITAPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2.2%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: [NO STEREO] OMBITASVIR
[NO STEREO] OMBITASVIR
 [NO STEREO] PARITAPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
900 mg single, oral
Highest studied dose
Dose: 900 mg
Route: oral
Route: single
Dose: 900 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26710243
healthy, 32.9 years (range: 18–55 years)
n = 6
Health Status: healthy
Age Group: 32.9 years (range: 18–55 years)
Sex: M+F
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/26710243
Sources:
https://pubmed.ncbi.nlm.nih.gov/26710243
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:85188
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85188
ZINC
ZINC000203757351
http://zinc15.docking.org/substances/ZINC000203757351
PubMed

PubMed

TitleDatePubMed
ABT-450 combined with ritonavir, in addition to ABT-333 and ribavirin: a race for an interferon-free regimen to cure HCV infection.
2013 Oct
ABT-450: a novel protease inhibitor for the treatment of hepatitis C virus infection.
2014
Efficacy and safety of paritaprevir/ritonavir, ombitasvir, and dasabuvir with ribavirin for the treatment of HCV genotype 1b compensated cirrhosis in patients aged 70 years or older.
2017 Dec
Safety and Efficacy of Ombitasvir, Paritaprevir With Ritonavir ± Dasabuvir With or Without Ribavirin in Patients With Human Immunodeficiency Virus-1 and Hepatitis C Virus Genotype 1 or Genotype 4 Coinfection: TURQUOISE-I Part 2.
2017 Summer
Patents

Patents

20100144608
2
20110312973
2
20120196792
2

Sample Use Guides

In Vivo Use Guide
50, 100 and 200 mg daily for 3 days (each dose in combination with 100 mg ribavirin).
Route of Administration: Oral
In Vitro Use Guide
To determine the breadth of coverage in genotype 1, the activity of Paritaprevir against chimeric replicons containing sequences derived from 11 genotype 1a- and 9 genotype 1b-infected patients was characterized. EC50s ranged from 0.43 to 1.87 nM against the genotype 1a isolates and from 0.033 to 0.087 nM against the genotype 1b isolates, indicating that Paritaprevir can inhibit NS3 proteases across a broad range of genotype 1 isolates.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:05:24 GMT 2023
Edited
by admin
on Fri Dec 15 16:05:24 GMT 2023
Record UNII
OU2YM37K86
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PARITAPREVIR
DASH   INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
(2R,6S,12Z,13aS,14aR,16aS)-N-(Cyclopropylsulfonyl)-6-{[(5-methylpyrazin-2-yl)carbonyl]amino}-5,16-dioxo-2-(phenanthridin-6-yloxy)-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
Systematic Name English
ABT-450
Code English
PARITAPREVIR [MI]
Common Name English
paritaprevir [INN]
Common Name English
VERUPREVIR ANHYDROUS
Common Name English
(2R,6S,12Z,13AS,14AR,16AS)-N-(CYCLOPROPYLSULFONYL)-6-(5-METHYLPYRAZIN-2-CARBOXAMIDO)-5,16-DIOXO-2-(PHENANTHRIDIN-6-YLOXY)-1,2,3,6,7,8,9,10,11,13A,14,15,16,16ATETRADECAHYDROCYCLOPROPA(E)PYRROLO(1,2-A)(1,4)DIAZACYCLOPENTADECINE-14A(5H)-CARBOXAMIDE
Systematic Name English
Paritaprevir [WHO-DD]
Common Name English
PARITAPREVIR [ORANGE BOOK]
Common Name English
PARITAPREVIR [USAN]
Common Name English
VIEKIRAX COMPONENT PARITAPREVIR
Brand Name English
PARITAPREVIR COMPONENT OF VIEKIRAX
Brand Name English
PARITAPREVIR [VANDF]
Common Name English
VERUPREVIR
Common Name English
Classification Tree Code System Code
WHO-ATC J05AX67
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
NCI_THESAURUS C783
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
WHO-ATC J05AP53
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
NDF-RT N0000182639
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
FDA ORPHAN DRUG 509215
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
WHO-ATC J05AP52
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
FDA ORPHAN DRUG 484715
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
WHO-ATC J05AX66
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
EMA ASSESSMENT REPORTS VIEKIRAX (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
Code System Code Type Description
EVMPD
SUB166312
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
FDA UNII
OU2YM37K86
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
CHEBI
85188
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
INN
9739
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
NDF-RT
N0000182638
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY HCV NS3/4A Protease Inhibitors [MoA]
USAN
BC-09
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
NDF-RT
N0000190108
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]
NDF-RT
N0000190107
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]
EVMPD
SUB131077
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
CAS
1216941-48-8
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
NDF-RT
N0000191272
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY UGT1A1 Inhibitors [MoA]
EPA CompTox
DTXSID601027922
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
PUBCHEM
45110509
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
DRUG BANK
DB09297
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
NDF-RT
N0000185503
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY P-Glycoprotein Inhibitors [MoA]
ChEMBL
CHEMBL3391662
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
RXCUI
1597373
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
Paritaprevir
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
NCI_THESAURUS
C123879
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
SMS_ID
100000157782
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
LACTMED
Paritaprevir
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
CAS
1221573-85-8
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
NO STRUCTURE GIVEN
MERCK INDEX
m11830
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
NDF-RT
N0000190113
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
LactMed
1216941-48-8
Created by admin on Fri Dec 15 16:05:24 GMT 2023 , Edited by admin on Fri Dec 15 16:05:24 GMT 2023
PRIMARY
Related Record Type Details
Structure of PARITAPREVIR
EXCRETED UNCHANGED
FECAL
HEPATITIS C VIRUS
TARGET ORGANISM->INHIBITOR
HCV NS3-4A SERINE PROTEASE
TARGET -> INHIBITOR
Structure of PARITAPREVIR DIHYDRATE
SOLVATE->ANHYDROUS
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Structure of PARITAPREVIR
EXCRETED UNCHANGED
URINE
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of (2R,6S,12Z,13AS,14AR,16AS)-6-AMINO-N-(CYCLOPROPYLSULFONYL)-1,2,3,6,7,8,9,10,11,13A,14,15,16,16A-TETRADECAHYDRO-5,16-DIOXO-2-(6-PHENANTHRIDINYLOXY)CYCLOPROPA(E)PYRROLO(1,2-A)(1,4)DIAZACYCLOPENTADECINE-14A(5H)-CARBOXAMIDE
METABOLITE -> PARENT
FECAL; URINE
Structure of S-((2R,6S,12S,13R,13AR,14AR,16AS)-14A-((CYCLOPROPYLSULFONYL)CARBAMOYL)-13-HYDROXY-6-(5-METHYLPYRAZINE-2-CARBOXAMIDO)-5,16-DIOXO-2-(PHENANTHRIDIN-6-YLOXY)OCTADECAHYDROCYCLOPROPA(E)PYRROLO(1,2-A)(1,4)DIAZACYCLOPENTADECIN-12-YL)-L-CYSTEINE
METABOLITE -> PARENT
FECAL
Structure of 5-METHYL-2-PYRAZINECARBOXYLIC ACID
METABOLITE -> PARENT
MAJOR
URINE
Related Record Type Details
Structure of PARITAPREVIR
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
blood-to-plasma ratio PHARMACOKINETIC
Tmax PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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