ARD-69

Size	Price	Stock	Quantity
--	$--	In stock

Size

Price

Stock

Quantity

$--

In stock

Purity

≥95%

Solubility

Soluble in DMSO

Appearance

Solid Powder

Storage

Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)

IUPACName

(2S,4R)-N-((S)-3-(4-((4-(((1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl)carbamoyl)phenyl)ethynyl)-[1,4'-bipiperidin]-1'-yl)-1-(4-(4-methylthiazol-5-yl)phenyl)-3-oxopropyl)-1-((S)-2-(1-fluorocyclopropane-1-carboxamido)-3,3-dimethylbutanoyl)-4-hydroxypyrrolidine-2-carboxamide

Synonyms

N-[(1-Fluorocyclopropyl)carbonyl]-3-methyl-L-valyl-(4R)-N-{(1S)-3-{4-[(4-{[trans-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl}phenyl)ethynyl]-1,4'-bipiperidin-1'-yl}-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]-3-oxopropyl}-4-hydroxy-L-prolinamide; L-Prolinamide, N-[(1-fluorocyclopropyl)carbonyl]-3-methyl-L-valyl-N-[(1S)-3-[4-[2-[4-[[[trans-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]amino]carbonyl]phenyl]ethynyl][1,4'-bipiperidin]-1'-yl]-1-[4-(4-methyl-5-thiazolyl)phenyl]-3-oxopropyl]-4-hydroxy-, (4R)-; (2S,4R)-N-[(1S)-3-[4-[4-[2-[4-[[(1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl]phenyl]ethynyl]piperidin-1-yl]piperidin-1-yl]-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]-3-oxopropyl]-1-[(2S)-2-[(1-fluorocyclopropanecarbonyl)amino]-3,3-dimethylbutanoyl]-4-hydroxypyrrolidine-2-carboxamide; ARD69; ARD 69

Density

1.34±0.1 g/cm3

InChI Key

CWGVEMFBQJUWLU-RXFAPWBBSA-N

InChI

InChI=1S/C62H74ClFN8O7S/c1-37-51(80-36-66-37)41-17-15-40(16-18-41)48(67-54(76)49-31-45(73)35-72(49)55(77)52(59(2,3)4)68-58(78)62(64)25-26-62)33-50(74)71-29-23-44(24-30-71)70-27-21-39(22-28-70)10-9-38-11-13-42(14-12-38)53(75)69-56-60(5,6)57(61(56,7)8)79-46-20-19-43(34-65)47(63)32-46/h11-20,32,36,39,44-45,48-49,52,56-57,73H,21-31,33,35H2,1-8H3,(H,67,76)(H,68,78)(H,69,75)/t45-,48+,49+,52-,56-,57-/m1/s1

Canonical SMILES

N#CC1=CC=C(OC2C(C)(C)C(NC(=O)C3=CC=C(C#CC4CCN(CC4)C5CCN(C(=O)CC(NC(=O)C6N(C(=O)C(NC(=O)C7(F)CC7)C(C)(C)C)CC(O)C6)C=8C=CC(=CC8)C=9SC=NC9C)CC5)C=C3)C2(C)C)C=C1Cl

1. Discovery of ARD-69 as a highly potent proteolysis targeting chimera (PROTAC) degrader of androgen receptor (AR) for the treatment of prostate cancer.

Han, X., Wang, C., Qin, C., Xiang, W., Fernandez-Salas, E., Yang, C.Y., Wang, M., Zhao, L., Xu, T., Chinnaswamy, K. and Delproposto, J., 2019. Journal of medicinal chemistry, 62(2), pp.941-964.

We report herein the discovery of highly potent PROTAC degraders of androgen receptor (AR), as exemplified by compound 34 (ARD-69). ARD-69 induces degradation of AR protein in AR-positive prostate cancer cell lines in a dose- and time-dependent manner. ARD-69 achieves DC50 values of 0.86, 0.76, and 10.4 nM in LNCaP, VCaP, and 22Rv1 AR+ prostate cancer cell lines, respectively. ARD-69 is capable of reducing the AR protein level by >95% in these prostate cancer cell lines and effectively suppressing AR-regulated gene expression. ARD-69 potently inhibits cell growth in these AR-positive prostate cancer cell lines and is >100 times more potent than AR antagonists. A single dose of ARD-69 effectively reduces the level of AR protein in xenograft tumor tissue in mice. Further optimization of ARD-69 may ultimately lead to a new therapy for AR+, castration-resistant prostate cancer.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂