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Details

Stereochemistry ACHIRAL
Molecular Formula C18H17Cl2F3N4O2
Molecular Weight 449.2549
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GW842166

SMILES

c1cc(c(cc1Cl)Cl)Nc2ncc(c(C(F)(F)F)n2)C(=NCC3CCOCC3)O

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 449.2549
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
63.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.285 μg/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
3.57 μg × h/mL
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
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

Doses

DosePopulationAdverse events​
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources: 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: Page: p.672, 673
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Discovery of 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain.
2007 May 31
Discovery and optimization of 1-(4-(pyridin-2-yl)benzyl)imidazolidine-2,4-dione derivatives as a novel class of selective cannabinoid CB2 receptor agonists.
2011 Oct 27
Patents

Sample Use Guides

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
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 Sat Jun 26 02:48:21 UTC 2021
Edited
by admin
on Sat Jun 26 02:48:21 UTC 2021
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
Created by admin on Sat Jun 26 02:48:21 UTC 2021 , Edited by admin on Sat Jun 26 02:48:21 UTC 2021
PRIMARY
PUBCHEM
10253143
Created by admin on Sat Jun 26 02:48:21 UTC 2021 , Edited by admin on Sat Jun 26 02:48:21 UTC 2021
PRIMARY
EPA CompTox
666260-75-9
Created by admin on Sat Jun 26 02:48:21 UTC 2021 , Edited by admin on Sat Jun 26 02:48:21 UTC 2021
PRIMARY
DRUG BANK
DB11903
Created by admin on Sat Jun 26 02:48:21 UTC 2021 , Edited by admin on Sat Jun 26 02:48:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL225411
Created by admin on Sat Jun 26 02:48:21 UTC 2021 , Edited by admin on Sat Jun 26 02:48:21 UTC 2021
PRIMARY
CAS
666260-75-9
Created by admin on Sat Jun 26 02:48:21 UTC 2021 , Edited by admin on Sat Jun 26 02:48:21 UTC 2021
PRIMARY
CAS
956013-38-0
Created by admin on Sat Jun 26 02:48:21 UTC 2021 , Edited by admin on Sat Jun 26 02:48:21 UTC 2021
SUPERSEDED
WIKIPEDIA
GW-842,166X
Created by admin on Sat Jun 26 02:48:21 UTC 2021 , Edited by admin on Sat Jun 26 02:48:21 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
potent and selective cannabinoid CB2 receptor agonist
Related Record Type Details
ACTIVE MOIETY