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Details

Stereochemistry ABSOLUTE
Molecular Formula C40H43N7O7S.2H2O
Molecular Weight 801.908
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PARITAPREVIR DIHYDRATE

SMILES

O.O.[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=AWGQIDLXYMGEEH-RHSIAEQTSA-N
InChI=1S/C40H43N7O7S.2H2O/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);2*1H2/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
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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 17:34:17 GMT 2023
Edited
by admin
on Fri Dec 15 17:34:17 GMT 2023
Record UNII
HRQ5901O78
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PARITAPREVIR DIHYDRATE
Common Name English
ABT-450 DIHYDRATE
Code English
PARITAPREVIR HYDRATE [JAN]
Common Name English
PARITAPREVIR DIHYDRATE [MI]
Common Name English
Code System Code Type Description
PUBCHEM
90479564
Created by admin on Fri Dec 15 17:34:17 GMT 2023 , Edited by admin on Fri Dec 15 17:34:17 GMT 2023
PRIMARY
CAS
1456607-71-8
Created by admin on Fri Dec 15 17:34:17 GMT 2023 , Edited by admin on Fri Dec 15 17:34:17 GMT 2023
PRIMARY
FDA UNII
HRQ5901O78
Created by admin on Fri Dec 15 17:34:17 GMT 2023 , Edited by admin on Fri Dec 15 17:34:17 GMT 2023
PRIMARY
CAS
1535165-38-8
Created by admin on Fri Dec 15 17:34:17 GMT 2023 , Edited by admin on Fri Dec 15 17:34:17 GMT 2023
NON-SPECIFIC STOICHIOMETRY
DRUG BANK
DBSALT002725
Created by admin on Fri Dec 15 17:34:17 GMT 2023 , Edited by admin on Fri Dec 15 17:34:17 GMT 2023
PRIMARY
MERCK INDEX
m11830
Created by admin on Fri Dec 15 17:34:17 GMT 2023 , Edited by admin on Fri Dec 15 17:34:17 GMT 2023
PRIMARY
CAS
1535165-41-3
Created by admin on Fri Dec 15 17:34:17 GMT 2023 , Edited by admin on Fri Dec 15 17:34:17 GMT 2023
ALTERNATIVE
RXCUI
1600436
Created by admin on Fri Dec 15 17:34:17 GMT 2023 , Edited by admin on Fri Dec 15 17:34:17 GMT 2023
PRIMARY RxNorm
Related Record Type Details
Structure of PARITAPREVIR
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of PARITAPREVIR
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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