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Details

Stereochemistry ABSOLUTE
Molecular Formula C50H67N7O8
Molecular Weight 894.1091
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OMBITASVIR

SMILES

COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC2=CC=C(C=C2)[C@@H]3CC[C@H](N3C4=CC=C(C=C4)C(C)(C)C)C5=CC=C(NC(=O)[C@@H]6CCCN6C(=O)[C@@H](NC(=O)OC)C(C)C)C=C5

InChI

InChIKey=PIDFDZJZLOTZTM-KHVQSSSXSA-N
InChI=1S/C50H67N7O8/c1-30(2)42(53-48(62)64-8)46(60)55-28-10-12-40(55)44(58)51-35-20-14-32(15-21-35)38-26-27-39(57(38)37-24-18-34(19-25-37)50(5,6)7)33-16-22-36(23-17-33)52-45(59)41-13-11-29-56(41)47(61)43(31(3)4)54-49(63)65-9/h14-25,30-31,38-43H,10-13,26-29H2,1-9H3,(H,51,58)(H,52,59)(H,53,62)(H,54,63)/t38-,39-,40-,41-,42-,43-/m0/s1

HIDE SMILES / InChI

Description

Ombitasvir (ABT-267) is an antiviral drug for the treatment of hepatitis C virus (HCV) infection. Ombitasvir is a potent inhibitor of the hepatitis C virus protein NS5A, has favorable pharmacokinetic characteristics and is active in the picomolar range against genotype 1 - 6. In 2015, it was approved by FDA for use in combination with paritaprevir, ritonavir and dasabuvir in the product Viekira Pak for the treatment of HCV genotype 1.

CNS Activity

CNS Non-penetrant
1014
Curator's Comment: Tissue distribution in rats was slow and did not permeate across the blood brain barrier or into the lens of the eye.

Originator

Approval Year

2015
471
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.68 pM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
VIEKIRA PAK (COPACKAGED)

Approved Use

VIEKIRA PAK with or without ribavirin is indicated for the treatment of patients with genotype 1 chronic hepatitis C virus (HCV) infection including those with compensated cirrhosis.

Launch Date

2014
Primary
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.

Launch Date

2015
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
68 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: [NO STEREO] PARITAPREVIR
[NO STEREO] PARITAPREVIR
 [NO STEREO] OMBITASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1000 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: [NO STEREO] PARITAPREVIR
[NO STEREO] PARITAPREVIR
 [NO STEREO] OMBITASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
23 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: [NO STEREO] PARITAPREVIR
[NO STEREO] PARITAPREVIR
 [NO STEREO] OMBITASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: [NO STEREO] PARITAPREVIR
[NO STEREO] PARITAPREVIR
 [NO STEREO] OMBITASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
200 mg 1 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://www.journal-of-hepatology.eu/article/S0168-8278(11)61206-3/abstract
https://pubmed.ncbi.nlm.nih.gov/28229375
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://www.journal-of-hepatology.eu/article/S0168-8278(11)61206-3/abstract
https://pubmed.ncbi.nlm.nih.gov/28229375
Sources:
https://www.journal-of-hepatology.eu/article/S0168-8278(11)61206-3/abstract
https://pubmed.ncbi.nlm.nih.gov/28229375
350 mg single, oral
Highest studied dose
Dose: 350 mg
Route: oral
Route: single
Dose: 350 mg
Sources:
https://www.journal-of-hepatology.eu/article/S0168-8278(11)61206-3/abstract
https://pubmed.ncbi.nlm.nih.gov/28229375
healthy
n = 6
Health Status: healthy
Population Size: 6
Sources:
https://www.journal-of-hepatology.eu/article/S0168-8278(11)61206-3/abstract
https://pubmed.ncbi.nlm.nih.gov/28229375
Sources:
https://www.journal-of-hepatology.eu/article/S0168-8278(11)61206-3/abstract
https://pubmed.ncbi.nlm.nih.gov/28229375
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:85183
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85183
MolPort
MolPort-039-137-483
https://www.molport.com/shop/molecule-link/MolPort-039-137-483
ZINC
ZINC000150601177
http://zinc15.docking.org/substances/ZINC000150601177
PubMed

PubMed

TitleDatePubMed
Discovery of ABT-267, a pan-genotypic inhibitor of HCV NS5A.
2014 Mar 13
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.
2015 Sep
Patents

Patents

20100317568
2
20120258909
2
20130102525
7
20130102526
5
20130102557
5
20130102558
5
20140024579
5

Sample Use Guides

In Vivo Use Guide
The direct-acting antiviral regimen of 25 mg ombitasvir-150 mg paritaprevir-100 mg ritonavir once daily (QD) plus 250 mg dasabuvir twice daily (BID) is approved for the treatment of hepatitis C virus genotype 1 infection, including patients coinfected with human immunodeficiency virus.
Route of Administration: Oral
In Vitro Use Guide
In vitro studies revealed that ABT-267 (ombitasvir) is a broad genotype NS5A inhibitor with antiviral activity in the picomolar range (EC50 1.7 -- 19.3 in genotype 1a, 1b, 2a, 3a, 4a and 5a, and 366 pM in genotype 6a).
Name Type Language
OMBITASVIR
DASH   INN   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ombitasvir [INN]
Common Name English
OMBITASVIR [MI]
Common Name English
OMBITASVIR [VANDF]
Common Name English
Ombitasvir [WHO-DD]
Common Name English
OMBITASVIR [ORANGE BOOK]
Common Name English
VIEKIRAX COMPONENT OMBITASVIR
Brand Name English
ABT-267
Code English
CARBAMIC ACID, N,N'-(((2S,5S)-1-(4-(1,1-DIMETHYLETHYL)PHENYL)-2,5-PYRROLIDINEDIYL)BIS(4,1-PHENYLENEIMINOCARBONYL-(2S)-2,1-PYRROLIDINEDIYL((1S)-1-(1-METHYLETHYL)-2-OXO-2,1-ETHANEDIYL)))BIS-, C,C'-DIMETHYL ESTER
Systematic Name English
OMBITASVIR [USAN]
Common Name English
OMBITASVIR COMPONENT OF VIEKIRAX
Brand Name English
Classification Tree Code System Code
WHO-ATC J05AP53
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
WHO-ATC J05AX67
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
FDA ORPHAN DRUG 484715
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
NCI_THESAURUS C281
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
WHO-ATC J05AP52
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
EMA ASSESSMENT REPORTS VIEKIRAX (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
FDA ORPHAN DRUG 509215
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
NDF-RT N0000191256
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
Code System Code Type Description
SMS_ID
100000156930
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
PUBCHEM
54767916
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
DRUG CENTRAL
4912
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
NCI_THESAURUS
C123878
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
RXCUI
1597371
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY RxNorm
FDA UNII
2302768XJ8
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
DRUG BANK
DB09296
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
WIKIPEDIA
Ombitasvir
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
USAN
BC-07
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
LACTMED
Ombitasvir
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
EVMPD
SUB131058
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
NDF-RT
N0000191272
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY UGT1A1 Inhibitors [MoA]
MERCK INDEX
m11829
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
INN
9740
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
ChEMBL
CHEMBL3127326
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID201027920
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
CAS
1258226-87-7
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
CHEBI
85183
Created by admin on Sat Dec 16 08:40:11 GMT 2023 , Edited by admin on Sat Dec 16 08:40:11 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of OMBITASVIR
METABOLITE (PARENT)
Structure of A-1246485
METABOLITE (PARENT)
Structure of A-1242846
METABOLITE (PARENT)
Structure of A-1543706
NIH
NCATS
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DISCLAIMER
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