RD162

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H16F4N4O2S
Molecular Weight	476.447
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=O)C1=C(F)C=C(C=C1)N2C(=S)N(C(=O)C23CCC3)C4=CC(=C(C=C4)C#N)C(F)(F)F

InChI

InChIKey=JPQFGMYHKSKKGW-UHFFFAOYSA-N

InChI=1S/C22H16F4N4O2S/c1-28-18(31)15-6-5-14(10-17(15)23)30-20(33)29(19(32)21(30)7-2-8-21)13-4-3-12(11-27)16(9-13)22(24,25)26/h3-6,9-10H,2,7-8H2,1H3,(H,28,31)

HIDE SMILES / InChI

Molecular Formula	C22H16F4N4O2S
Molecular Weight	476.447
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/19359544
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21397833

RD 162 was optimized from a screen for non-steroidal antiandrogens that retain activity in the setting of increased androgen receptor expression. RD 162 binds to the androgen receptor with greater relative affinity than the clinically used antiandrogen bicalutamide, reduce the efficiency of its nuclear translocation and impair both DNA binding to androgen response elements and recruitment of coactivators. RD 162 is orally available and induce tumor regression in mouse models of castration-resistant human prostate cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19359544	Antagonist 2778		50.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21397833	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Development of a second-generation antiandrogen for treatment of advanced prostate cancer.	2009 May 8	19359544
Androgen receptor amplification is reflected in the transcriptional responses of Vertebral-Cancer of the Prostate cells.	2011 Jan 1	20728506
[Strategies in castration-resistant prostate cancer].	2011 Mar	21397833

Patents

Sample Use Guides

In Vivo Use Guide

Mice: mice were treated for 5 days with 10 mg/kg RD 162 daily by oral gavage

Route of Administration: Oral

In Vitro Use Guide

In the human prostate cancer cell line VCaP which has endogenous AR gene amplification, RD 162 (1 and 10 uM) suppressed growth and induced apoptosis

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:43:29 UTC 2023` Edited by `admin` on `Sat Dec 16 18:43:29 UTC 2023`
Record UNII	5ZE6THH5VF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RD162

Code

English

N-Methyl-4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl]-2-fluorobenzamide

Systematic Name

English

4-[7-[4-Cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-2-fluoro-N-methylbenzamide

Systematic Name

English

RD-162

Code

English

Benzamide, 4-[7-[4-cyano-3-(trifluoromethyl)phenyl]-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-2-fluoro-N-methyl-

Systematic Name

English

Code System Code Type Description

PUBCHEM

11957756