PF-4455242

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H28N2O2S.ClH
Molecular Weight	408.985
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)CNCC1=CC=C(C=C1)C2=CC=CC=C2S(=O)(=O)N3CCCC3

InChI

InChIKey=WRNZYMZEVIVCFL-UHFFFAOYSA-N

InChI=1S/C21H28N2O2S.ClH/c1-17(2)15-22-16-18-9-11-19(12-10-18)20-7-3-4-8-21(20)26(24,25)23-13-5-6-14-23;/h3-4,7-12,17,22H,5-6,13-16H2,1-2H3;1H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21744827 | https://www.ncbi.nlm.nih.gov/pubmed/21821697
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800030611

Pfizer was developing PF-4455242, a selective, short-acting (non-"inactivating") antagonist of the κ-opioid receptor. PF-4455242 was pursued in phase I clinical trial for the treatment of the bipolar disorder and was also investigated as a treatment for depression and substance abuse. In September 2010 Pfizer discontinued the development of the compound.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24690494	Antagonist 2849		10.0 nM [Ki]
Kappa opioid receptor 115 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21744827 \| https://www.ncbi.nlm.nih.gov/pubmed/21821697	Antagonist 2849		1.23 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bipolar disorder 34 Sources: http://adisinsight.springer.com/drugs/800030611 https://clinicaltrials.gov/ct2/show/NCT00939887	Primary		Phase I 438	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacological characterization of 2-methyl-N-((2'-(pyrrolidin-1-ylsulfonyl)biphenyl-4-yl)methyl)propan-1-amine (PF-04455242), a high-affinity antagonist selective for κ-opioid receptors.	2011-11	21821697
Design and discovery of a selective small molecule κ opioid antagonist (2-methyl-N-((2'-(pyrrolidin-1-ylsulfonyl)biphenyl-4-yl)methyl)propan-1-amine, PF-4455242).	2011-08-25	21744827

Sample Use Guides

In Vivo Use Guide

Single dose of up to 30 mg PF-4455242, delivered in capsule.

Route of Administration: Oral

In Vitro Use Guide

PF-4455242 bound with high affinity to human KOR stably expressed in CHO cells with an average Ki value of 3.0 nM

Name

Type

Language

PF-4455242

Common Name

English

PF 4455242

Preferred Name

English

(1,1'-BIPHENYL)-4-METHANAMINE, N-(2-METHYLPROPYL)-2'-(1-PYRROLIDINYLSULFONYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

PUBCHEM

53465410