GW842166

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H17Cl2F3N4O2
Molecular Weight	449.254
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC(F)(F)C1=NC(NC2=CC=C(Cl)C=C2Cl)=NC=C1C(=O)NCC3CCOCC3

InChI

InChIKey=TWQYWUXBZHPIIV-UHFFFAOYSA-N

InChI=1S/C18H17Cl2F3N4O2/c19-11-1-2-14(13(20)7-11)26-17-25-9-12(15(27-17)18(21,22)23)16(28)24-8-10-3-5-29-6-4-10/h1-2,7,9-10H,3-6,8H2,(H,24,28)(H,25,26,27)

HIDE SMILES / InChI

Molecular Formula	C18H17Cl2F3N4O2
Molecular Weight	449.254
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://adisinsight.springer.com/drugs/800021826
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17477516 http://www.selleckchem.com/products/gw-842166x.html

GW842166 is a pyrimidine cannabinoid 2 (CB2) receptor agonist that was being developed by GlaxoSmithKline for the treatment of inflammatory pain. It has potent analgesic, anti-inflammatory and anti-hyperalgesic actions in animal models, but without cannabis-like behavioural effects due to its extremely low affinity for the CB1 receptor. GW842166 shows similar potency and efficacy for rat and human recombinant CB2 receptors with EC50 of 91 nM and 63nM, respectively. GW842166 is in Phase 2 trial.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18255291	Agonist 2678		63.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoarthritis 157 Sources: https://clinicaltrials.gov/ct2/show/NCT00447486	Palliative		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.285 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21540741	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		GW842166 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.714 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21540741	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:		GW842166 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
3.57 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21540741	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		GW842166 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.01 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21540741	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:		GW842166 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/21540741 Page: p.672, 673	unhealthy, ADULT n = 27 Health Status: unhealthy Condition: pain disorder Age Group: ADULT Sex: M+F Food Status: FED Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/21540741 Page: p.672, 673	Sources: https://pubmed.ncbi.nlm.nih.gov/21540741 Page: p.672, 673

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1478 CYP1A2 1524 P-gp 1461

Drug as perpetrator

Target	Modality	Activity
P-gp 1650	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363677524	inconclusive [IC50 4.6109 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17477516/	no [IC50 >100 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17477516/	no [IC50 >100 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17477516/	no [IC50 >100 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17477516/	no [IC50 >100 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17477516/	no [IC50 >100 uM]

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	2455AH	https://aksci.com/item_detail.php?cat=2455AH
ApexBio Technology	B1428	https://www.apexbt.com/catalogsearch/result/?q=B1428
Axon MedChem	1925	https://www.axonmedchem.com/product/1925
BOC Sciences	666260-75-9	http://www.bocsci.com/description.asp?cas=666260-75-9
Cayman Chemical	10010372	http://www.caymanchem.com/app/template/Product.vm/catalog/10010372
Chem Scene	CS-7768	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7768
ChemShuttle	151769	https://www.chemshuttle.com/catalogsearch/result/?q=151769
MedChem Express	HY-14167	https://www.medchemexpress.com/search.html?q=HY-14167&ft=&fa=&fp=
MolPort	MolPort-009-019-316	https://www.molport.com/shop/molecule-link/MolPort-009-019-316
Molnova	M18967	https://www.molnova.com/en/serch-list.html?keywords=M18967
MuseChem	R039808	https://www.musechem.com/product/R039808.html
ShangHai Biochempartner	BCP000608	http://www.biochempartner.com/search_BCP000608
ShangHai Biochempartner	BCP05306	http://www.biochempartner.com/search_BCP05306
TargetMol	T6527	https://www.targetmol.com/search?keyword=T6527
Toronto Research Chemicals	D293280	https://www.trc-canada.com/product-detail/?CatNum=D293280
Toronto Research Chemicals	G931520	https://www.trc-canada.com/product-detail/?CatNum=G931520
eMolecules	25041239	https://orderbb.emolecules.com/search/#?query=25041239
eNovation Chemicals	D371903	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D371903&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-4676972687	https://mcule.com/MCULE-4676972687/

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

single doses of GW842166 (100 and 800 mg) failed to demonstrate clinically meaningful analgesia in the setting of acute dental pain.

Route of Administration: Oral

In Vitro Use Guide

CB2 receptor binding was blocked by preincubating mouse T cells with the CB2 agonist GW 842166X at 100 uM

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:02:09 UTC 2023` Edited by `admin` on `Fri Dec 15 16:02:09 UTC 2023`
Record UNII	VL1I6P2DZ8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GW842166

Common Name

English

GW 842166

Code

English

GW-842,166X

Common Name

English

GW842166X

Code

English

5-PYRIMIDINECARBOXAMIDE, 2-((2,4-DICHLOROPHENYL)AMINO)-N-((TETRAHYDRO-2H-PYRAN-4-YL)METHYL)-4-(TRIFLUOROMETHYL)-

Systematic Name

English

GW-842166

Code

English

2-(2,4-DICHLOROPHENYLAMINO)-4-TRIFLUOROMETHYLPYRIMIDINE-5-CARBOXYLIC ACID ((TETRAHYDROPYRAN-4-YL)METHYL)AMIDE

Systematic Name

English

GW 842166X

Code

English

Code System Code Type Description

FDA UNII

VL1I6P2DZ8