PF-514273

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H17Cl2F2N3O2
Molecular Weight	452.281
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(F)(F)CN1CCOC2=C(N(N=C2C1=O)C3=CC=CC=C3Cl)C4=CC=C(Cl)C=C4

InChI

InChIKey=FJMQJSUOOGOWBD-UHFFFAOYSA-N

InChI=1S/C21H17Cl2F2N3O2/c1-21(24,25)12-27-10-11-30-19-17(20(27)29)26-28(16-5-3-2-4-15(16)23)18(19)13-6-8-14(22)9-7-13/h2-9H,10-12H2,1H3

HIDE SMILES / InChI

Molecular Formula	C21H17Cl2F2N3O2
Molecular Weight	452.281
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/19351113
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800025584

PF-514273 is a drug developed by Pfizer, which acts as an extremely selective antagonist for the CB1 receptor, with approximately 10,000x selectivity over the closely related CB2 receptor. Pfizer was developing PF 514273 in phase I clinical studies for the treatment of obesity in the US. However, these studies were discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid CB1 receptor 85 Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19351113	Antagonist 2778		1.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19351113	Primary		Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Discovery of 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-6,7-dihydro-2H-pyrazolo[3,4-f][1,4]oxazepin-8(5H)-one (PF-514273), a novel, bicyclic lactam-based cannabinoid-1 receptor antagonist for the treatment of obesity.	2009 May 14	19351113
Effects of the novel cannabinoid CB1 receptor antagonist PF 514273 on the acquisition and expression of ethanol conditioned place preference.	2014 Aug	24954022

Patents

Sample Use Guides

In Vivo Use Guide

Mice: PF 514273 was prepared in a vehicle of 50% dH2O and 50% DMSO and injected IP in a 5-mL/kg volume at 1- and 5-mg/kg doses.

Route of Administration: Intraperitoneal

In Vitro Use Guide

PF-514273 binds human CB1 receptor with Ki 1nM

Substance Class	Chemical Created by `admin` on `Sat Dec 16 12:04:45 GMT 2023` Edited by `admin` on `Sat Dec 16 12:04:45 GMT 2023`
Record UNII	45FRJ4YGM2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PF-514273

Common Name

English

2-(2-CHLOROPHENYL)-3-(4-CHLOROPHENYL)-7-(2,2-DIFLUOROPROPYL)-6,7-DIHYDRO-2H-PYRAZOLO(3,4-F)(1,4)OXAZEPIN-8(5H)-ONE

Systematic Name

English

PF 0514273

Code

English

PF 514273

Code

English

2H-PYRAZOLO(3,4-F)(1,4)OXAZEPIN-8(5H)-ONE, 2-(2-CHLOROPHENYL)-3-(4-CHLOROPHENYL)-7-(2,2-DIFLUOROPROPYL)-6,7-DIHYDRO-

Systematic Name

English

Code System Code Type Description

FDA UNII

45FRJ4YGM2