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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 of GW842166

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
63.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
0.285 μg/mL
100 mg single, oral
GW842166 plasma
Homo sapiens
0.714 μg/mL
800 mg single, oral
GW842166 plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3.57 μg × h/mL
100 mg single, oral
GW842166 plasma
Homo sapiens
9.01 μg × h/mL
800 mg single, oral
GW842166 plasma
Homo sapiens

Doses

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

PubMed

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
Record UNII
VL1I6P2DZ8
Record Status Validated (UNII)
Record Version