OMBITASVIR

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

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

Molecular Formula	C50H67N7O8
Molecular Weight	894.1091
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nonstructural protein 5A 11	Inhibitor 8,297		0.68 pM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Genotype 1 chronic hepatitis C virus (HCV) infection 2	Primary		Approved 8,429	VIEKIRA PAK (COPACKAGED)
Genotype 4 chronic hepatitis C virus (HCV) infection without cirrhosis 2	Primary		Approved 8,429	TECHNIVIE

C_max

Value	Dose	Co-administered	Analyte	Population
68 ng/mL	25 mg 1 times / day steady-state, oral	[NO STEREO] PARITAPREVIR	[NO STEREO] OMBITASVIR plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1000 ng × h/mL	25 mg 1 times / day steady-state, oral	[NO STEREO] PARITAPREVIR	[NO STEREO] OMBITASVIR plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
23 h	25 mg 1 times / day steady-state, oral	[NO STEREO] PARITAPREVIR	[NO STEREO] OMBITASVIR plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.1%	25 mg 1 times / day steady-state, oral	[NO STEREO] PARITAPREVIR	[NO STEREO] OMBITASVIR plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
200 mg 1 times / day multiple, oral Highest studied dose	healthy n = 6
350 mg single, oral Highest studied dose	healthy n = 6

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
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

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PubMed

Title	Date	PubMed
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.	2015 Sep	25937625

Patents

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).