TEGOBUVIR

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H14F7N5
Molecular Weight	517.401
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=CC=C1C2=NC3=CN(CC4=NN=C(C=C4)C5=CC=C(C=C5C(F)(F)F)C(F)(F)F)C=CC3=N2

InChI

InChIKey=XBEQSQDCBSKCHJ-UHFFFAOYSA-N

InChI=1S/C25H14F7N5/c26-19-4-2-1-3-17(19)23-33-21-9-10-37(13-22(21)34-23)12-15-6-8-20(36-35-15)16-7-5-14(24(27,28)29)11-18(16)25(30,31)32/h1-11,13H,12H2

HIDE SMILES / InChI

Molecular Formula	C25H14F7N5
Molecular Weight	517.401
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/24501005
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22720059

GS-9190 (Tegobuvir) a novel nonnucleoside inhibitor of hepatitis C virus NS5B polymerase was investigated for treatment Hepatitis C, Chronic, but on the clinical trial II was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nonstructural protein 5B 1 Target ID: Nonstructural protein 5B Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=21746939	Binding Agent 1064		71.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis C 42 Sources: https://clinicaltrials.gov/ct2/show/NCT01353248	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34011	https://www.001chemical.com/chem/search?q=DY34011
1PlusChem LLC	1P008U0J	https://www.1pchem.com/search?query=1P008U0J
AChemBlock	M23584	http://www.achemblock.com/catalogsearch/result/?q=M23584
AK Scientific	4092AH	https://aksci.com/item_detail.php?cat=4092AH
Alfa Chemistry	ACM1000787756	http://www.alfa-chemistry.com/search.aspx?q=ACM1000787756
ApexBio Technology	A3864	https://www.apexbt.com/catalogsearch/result/?q=A3864
AstaTech	42290	http://astatechinc.com/CPSResult.php?CRNO=42290
BLD Pharm	BD332244	http://www.bldpharm.com/search/Search.html?keyword=BD332244
BOC Sciences	1000787-75-6	http://www.bocsci.com/description.asp?cas=1000787-75-6
BioSynth	W-204340	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-204340
Chem Scene	CS-0672	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0672
Hairui	HR151313	http://www.hairuichem.com/en/product/search.do?q=HR151313
KeyOrganics	AS-74871	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-74871
MedChem Express	HY-10544	https://www.medchemexpress.com/search.html?q=HY-10544&ft=&fa=&fp=
MolPort	MolPort-020-393-276	https://www.molport.com/shop/molecule-link/MolPort-020-393-276
Molcore	MC34011	http://www.molcore.com/CatMC34011.html
Molnova	M10009	https://www.molnova.com/en/serch-list.html?keywords=M10009
eMolecules	36096047	https://orderbb.emolecules.com/search/#?query=36096047
mcule	MCULE-9796621883	https://mcule.com/MCULE-9796621883/

PubMed

Title	Date	PubMed
The HCV non-nucleoside inhibitor Tegobuvir utilizes a novel mechanism of action to inhibit NS5B polymerase function.	2012	22720059
In vitro efficacy of approved and experimental antivirals against novel genotype 3 hepatitis C virus subgenomic replicons.	2013 Nov	24013001
Inhibition of hepatitis C virus replication by GS-6620, a potent C-nucleoside monophosphate prodrug.	2014	24419349
Imidazopyridazine hepatitis C virus polymerase inhibitors. Structure-activity relationship studies and the discovery of a novel, traceless prodrug mechanism.	2014 Mar 13	24224729

Patents

Sample Use Guides

In Vivo Use Guide

30 mg twice daily

Route of Administration: Oral

In Vitro Use Guide

Treatment of Hepatitis C Virus (HCV) subgenomic replicon cells with 50 nM (∼50 fold over EC50) Tegobuvir (TGV) results in a modified form of NS5B with a distinctly altered mobility on a SDS-PAGE gel. Furthermore analysis of NS5B protein purified from a heterologous expression system treated with TGV by mass spectrometry suggests that TGV undergoes a CYP- mediated intracellular activation step and the resulting metabolite, after forming a glutathione conjugate, directly and specifically interacts with NS5B. Taken together, these data demonstrate that upon metabolic activation TGV is a specific, covalent inhibitor of the HCV NS5B polymerase and is mechanistically distinct from other classes of the non-nucleoside inhibitors (NNI) of the viral polymerase.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:48:20 GMT 2023` Edited by `admin` on `Fri Dec 15 18:48:20 GMT 2023`
Record UNII	5NOK5X389M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEGOBUVIR

Official Name

English

tegobuvir [INN]

Common Name

English

5-({6-[2,4-Bis(trifluoromethyl)phenyl]pyridazin-3-yl}methyl)-2-(2-fluorophenyl)-5H-imidazo[4,5-c]pyridine

Systematic Name

English

GS-9190

Code

English

5H-IMIDAZO(4,5-C)PYRIDINE, 5-((6-(2,4-BIS(TRIFLUOROMETHYL)PHENYL)-3-PYRIDAZINYL)METHYL)- 2-(2-FLUOROPHENYL)-

Systematic Name

English

TEGOBUVIR [USAN]

Common Name

English

Tegobuvir [WHO-DD]

Common Name

English

GS-333126

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C783