U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
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] PARITAPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2220 ng × h/mL
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] PARITAPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.5 h
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] PARITAPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2.2%
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] 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:
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:
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
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.
2015 Sep
Ombitasvir/paritaprevir/ritonavir + dasabuvir ± ribavirin for treatment of chronic hepatitis C 1 genotype in the Republic of Belarus.
2017 Sep
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
Twelve weeks of ombitasvir/paritaprevir/r and dasabuvir without ribavirin is effective and safe in the treatment of patients with HCV genotype 1b infection and compensated cirrhosis: results from a real-world cohort study.
2018 Mar
Patents

Sample Use Guides

50, 100 and 200 mg daily for 3 days (each dose in combination with 100 mg ribavirin).
Route of Administration: Oral
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
EXCRETED UNCHANGED
FECAL
TARGET ORGANISM->INHIBITOR
TARGET -> INHIBITOR
SOLVATE->ANHYDROUS
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
URINE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
blood-to-plasma ratio PHARMACOKINETIC
Tmax PHARMACOKINETIC