OMBITASVIR HEMINONAHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C50H67N7O8.9H2O
Molecular Weight	1950.3557
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.O.O.O.O.O.O.O.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.COC(=O)N[C@@H](C(C)C)C(=O)N7CCC[C@H]7C(=O)NC8=CC=C(C=C8)[C@@H]9CC[C@H](N9C%10=CC=C(C=C%10)C(C)(C)C)C%11=CC=C(NC(=O)[C@@H]%12CCCN%12C(=O)[C@@H](NC(=O)OC)C(C)C)C=C%11

InChI

InChIKey=AWMWWEBJJCSJHI-MVJJBPFMSA-N

InChI=1S/2C50H67N7O8.9H2O/c2*1-30(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;;;;;;;;;/h2*14-25,30-31,38-43H,10-13,26-29H2,1-9H3,(H,51,58)(H,52,59)(H,53,62)(H,54,63);9*1H2/t2*38-,39-,40-,41-,42-,43-;;;;;;;;;/m00........./s1

HIDE SMILES / InChI

Molecular Formula	C50H67N7O8
Molecular Weight	894.1091
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25347030 | https://www.ncbi.nlm.nih.gov/pubmed/25074011 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206619lbl.pdf

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 Target ID: CHEMBL3307224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25347030 \| https://www.ncbi.nlm.nih.gov/pubmed/25074011 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206619s003lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/25451055	Inhibitor 8297		0.68 pM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Genotype 1 chronic hepatitis C virus (HCV) infection 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25347030 https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206619s003lbl.pdf	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 1.4189472E12
Genotype 4 chronic hepatitis C virus (HCV) infection without cirrhosis 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/207931s001lbl.pdf https://clinicaltrials.gov/ct2/show/NCT02487199	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 1.437696E12

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

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

PubMed

Title	Date	PubMed
Discovery of ABT-267, a pan-genotypic inhibitor of HCV NS5A.	2014 Mar 13	24400777
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).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:51:58 UTC 2023` Edited by `admin` on `Sat Dec 16 06:51:58 UTC 2023`
Record UNII	EQE3I70J3W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OMBITASVIR HEMINONAHYDRATE

Common Name

English

ABT-267 HEMINONAHYDRATE

Code

English

L-PROLINAMIDE, 2,2'-(((2S,5S)-1-(4-(1,1-DIMETHYLETHYL)PHENYL)-2,5-PYRROLIDINEDIYL)DI-4,1-PHENYLENE)BIS(N-(METHOXYCARBONYL)-L-VALYL-, HYDRATE (2:9)

Systematic Name

English

OMBITASVIR HYDRATE [JAN]

Common Name

English

Code System Code Type Description

FDA UNII

EQE3I70J3W