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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 of RD162

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

Description

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 TargetPharmacologyConditionPotency
50.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

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
Record UNII
5ZE6THH5VF
Record Status Validated (UNII)
Record Version