VESATOLIMOD

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H30N6O2
Molecular Weight	410.5126
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCOC1=NC2=C(NC(=O)CN2CC3=CC(CN4CCCC4)=CC=C3)C(N)=N1

InChI

InChIKey=VFOKSTCIRGDTBR-UHFFFAOYSA-N

InChI=1S/C22H30N6O2/c1-2-3-11-30-22-25-20(23)19-21(26-22)28(15-18(29)24-19)14-17-8-6-7-16(12-17)13-27-9-4-5-10-27/h6-8,12H,2-5,9-11,13-15H2,1H3,(H,24,29)(H2,23,25,26)

HIDE SMILES / InChI

Molecular Formula	C22H30N6O2
Molecular Weight	410.5126
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/?term=27799218

Vesatolimod, also known as GS-9620, is being developed in clinical studies for the treatment of chronic hepatitis B viral (HBV) infection, with the goal of inducing a liver-targeted antiviral effect without inducing the adverse effects associated with current systemic interferon-α (IFN-α) therapies. It is demonstrate interferon-stimulated gene induction without detectable serum interferon at low oral doses. GS-9620 is a potent and oral agonist of Toll-like receptor-7, a pattern-recognition receptor whose activation results in innate and adaptive immune stimulation

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Toll-like receptor 7 12 Target ID: CHEMBL5936 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23961878	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis B 16 Sources: https://clinicaltrials.gov/ct2/show/NCT02166047	Primary		Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	HLM 31 P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=440681462	inconclusive [IC50 15.0916 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=440681462	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=440681462	yes [IC50 3.3786 uM]

Drug as victim

Target	Modality	Activity
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363680873	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25733157/	yes
HLM 31	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30129284/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY425426	https://www.001chemical.com/chem/search?q=DY425426
1PlusChem LLC	1P003BAN	https://www.1pchem.com/search?query=1P003BAN
A2B Chem	AB53807	http://a2bchem.com/prod/AB53807
AChemBlock	I-9835	http://www.achemblock.com/catalogsearch/result/?q=I-9835
AOBIOUS INC	AOB87720	http://aobious.com/aobious/search?search_query=AOB87720
Angene	AGN-PC-0WCRIS	http://www.angenechemical.com/productshow/AGN-PC-0WCRIS.html
ApexBio Technology	A3444	https://www.apexbt.com/catalogsearch/result/?q=A3444
AstaTech	42241	http://astatechinc.com/CPSResult.php?CRNO=42241
BLD Pharm	BD254187	http://www.bldpharm.com/search/Search.html?keyword=BD254187
Cayman Chemical	19628	http://www.caymanchem.com/app/template/Product.vm/catalog/19628
Chem Scene	CS-1352	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1352
ChemShuttle	113838	https://www.chemshuttle.com/catalogsearch/result/?q=113838
Combi-Blocks	QJ-6609	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-6609
Debye Scientific	DA-33595	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-33595
Excenen	EX-A2065	http://www.excenen.com/searchresultlist.php?id=EX-A2065
KeyOrganics	AS-74316	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-74316
Matrix Scientific	147898	http://www.matrixscientific.com/147898.html
MedChem Express	HY-15601	https://www.medchemexpress.com/search.html?q=HY-15601&ft=&fa=&fp=
MolPort	MolPort-038-387-808	https://www.molport.com/shop/molecule-link/MolPort-038-387-808
Molcore	MC425426	http://www.molcore.com/CatMC425426.html
Molnova	M17205	https://www.molnova.com/en/serch-list.html?keywords=M17205
MuseChem	I000892	https://www.musechem.com/product/I000892.html
Selleck Chemicals	S7221	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7221
ShangHai Biochempartner	BCP08305	http://www.biochempartner.com/search_BCP08305
Synthonix	11127	https://synthonix.com/catalogsearch/result/?q=11127
TargetMol	T6846	https://www.targetmol.com/search?keyword=T6846
eMolecules	260885599	https://orderbb.emolecules.com/search/#?query=260885599
eMolecules	49383435	https://orderbb.emolecules.com/search/#?query=49383435
eNovation Chemicals	D372355	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372355&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1046276887	https://mcule.com/MCULE-1046276887/

PubMed

Title	Date	PubMed
GS-9620, an oral agonist of Toll-like receptor-7, induces prolonged suppression of hepatitis B virus in chronically infected chimpanzees.	2013 Jun	23415804
TLR7 Agonist GS-9620 Is a Potent Inhibitor of Acute HIV-1 Infection in Human Peripheral Blood Mononuclear Cells.	2017 Jan	27799218

Patents

Sample Use Guides

In Vivo Use Guide

1, 2, or 4 mg tablets administered orally every 7 days

Route of Administration: Oral

In Vitro Use Guide

The antiviral activity of GS-9620 was assessed in isolated macrophages, CD4+T cells and in total peripheral blood mononuclear cells (PBMCs) following infections with a replication component HIV-1BaL. In uninfected cultures, the viability of each cell type remained unchanged up to 10 μM GS-9620, the maximum concentration tested. GS-9620 was inactive against HIV in isolated CD4+ T cells and macrophages up to the highest concentration tested (10 µM), but did show dose-dependent inhibition of HIV-1 replication in complete PBMCs following infection with either HIV-1BaL (EC50 = 536 nM) or HIV-1VSVg (EC50 = 953 nM). Although GS-9620-mediated antiretroviral activity varied significantly between individual donors, its antiretroviral potency in PBMCs was enhanced by approximately 35-fold when GS-9620 was added 48 hours prior to infection with HIV-1VSVg (EC50 = 27 nM).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:49:05 UTC 2023` Edited by `admin` on `Sat Dec 16 02:49:05 UTC 2023`
Record UNII	O8M467C50G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VESATOLIMOD

Official Name

English

4-Amino-2-butoxy-8-({3-[(pyrrolidin-1-yl)methyl]phenyl}methyl)-7,8-dihydropteridin-6(5H)-one

Systematic Name

English

vesatolimod [INN]

Common Name

English

GS-9620

Code

English

VESATOLIMOD [USAN]

Common Name

English

Vesatolimod [WHO-DD]

Common Name

English

6(5H)-PTERIDINONE, 4-AMINO-2-BUTOXY-7,8-DIHYDRO-8-((3-(1-PYRROLIDINYLMETHYL)PHENYL)METHYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281