GLPBio

ARN-509

Catalog No.: GC16840Purity:>99.50%Synonyms: ARN 509; ARN509; Apalutamide
COASDSData Sheet
ARN-509 is a synthetic biaryl thiohydantoin compound that inhibits androgen receptor (AR), with an IC50 value of 16nM.

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ARN-509
Cas No.: 956104-40-8
10mM (in 1mL DMSO)In Stock
$73.00
1
5mgIn Stock
$57.00
1
10mgIn Stock
$98.00
1
50mgIn Stock
$259.00
1
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Description

ARN-509 is a synthetic biaryl thiohydantoin compound that inhibits androgen receptor (AR), with an IC50 value of 16nM[1]. ARN-509 irreversibly binds to the ligand binding domain of the AR with high affinity, induces conformational changes in AR, hinders the translocation of the receptor complex to the nucleus, and thereby prevents its binding to androgen response elements[2]. ARN-509 has been widely used in the related research on prostate cancer treatment[3].

In vitro, ARN-509 treatment (100μM; 24h) significantly inhibited the proliferation of 22Rv1 cells, and suppressed nuclear entry of AR, AR-V7, and phosphorylated AR[4]. Treatment with 10μM ARN-509 significantly inhibited AR signal transduction in LNCaP prostate cancer cell lines, resulting in reduced cell proliferation[1].

In vivo, ARN-509 treatment through oral gavage at a dose of 30mg/kg/day for 60 weeks, which significantly reduced the incidence of prostate cancer induced by N-methyl-N-nitrosourea in male Wistar rats[5]. In the LNCaP/AR castration-resistant prostate cancer (CRPC) mouse model, an oral administration dose of 10mg/kg/day of ARN-509 can significantly inhibit tumor regression[6]. In genetically engineered mouse prostate cancer (GEM-PCa) models, four weeks of oral treatment with ARN-509 (30mg/kg/day) significantly reduced tumor burden by 33.5% and increased PI3K-AKT signaling[7].

References:
[1]Clegg N J, Wongvipat J, Joseph J D, et al. ARN-509: a novel antiandrogen for prostate cancer treatment[J]. Cancer research, 2012, 72(6): 1494-1503.
[2]Smith M R, Antonarakis E S, Ryan C J, et al. Phase 2 study of the safety and antitumor activity of apalutamide (ARN-509), a potent androgen receptor antagonist, in the high-risk nonmetastatic castration-resistant prostate cancer cohort[J]. European urology, 2016, 70(6): 963-970.
[3]Smith M R, Antonarakis E S, Ryan C J, et al. ARN-509 in men with high risk non-metastatic castration-resistant prostate cancer[J]. Annals of Oncology, 2012, 23: ix303.
[4]Koukourakis M I, Kakouratos C, Kalamida D, et al. Comparison of the effect of the antiandrogen apalutamide (ARN-509) versus bicalutamide on the androgen receptor pathway in prostate cancer cell lines[J]. Anti-cancer drugs, 2018, 29(4): 323-333.
[5]Murillo G, Peng X, Muzzio M, et al. Exceptional activity of ARN-509 (apalutamide) in prostate cancer prevention in rats[J]. Cancer Research, 2019, 79(13_Supplement): 2730-2730.
[6]Hager J H, Smith N D, Bischoff E, et al. Effect of the novel anti-androgen ARN-509 on response and seizure in castration-resistant prostate cancer models[J]. Journal of Clinical Oncology, 2011, 29(7_suppl): 28-28.
[7]Velasco M A D, Nozawa M, Kura Y, et al. Apalutamide (ARN-509) demonstrates therapeutic efficacy in genetically engineered mouse models of Pten-deficient prostate cancer[J]. Cancer Research, 2018, 78(13_Supplement): 3737-3737.

Protocol

Cell experiment [1]:

Cell lines

22Rv1 cells

Preparation Method

2.5×10322Rv1 cells were inoculated in each well on a 96-well plate and incubated for 24 hours to allow the cells to attach to the well surface. Then, the cells were exposed to ARN-509 (10, 50, and 100μM; 24h) and Testosterone (10μmol/L; 24h). The effects on cell viability were tested when the ARN-509 and Testosterone were continuously present in the culture medium. To assess cell viability, 10%v/v AlamarBlue was added to each well. As a negative control (background measurement), ARN-509 was not contained in the culture medium. Vitamin C (5μl/well) was used as the positive control to completely reduce rizulin. Seven hours later, the relative fluorescence (in RFU: fluorescence per well minus background fluorescence) was measured using the microplate reader. Measure every other day from day 0 (24 hours after sowing) to day 6. The experiments were conducted under normal hypoxia and 1% hypoxia conditions.

Reaction Conditions

10, 50, and 100μM; 24h

Applications

ARN-509 significantly inhibited the viability of 22Rv1 cells in a dose-dependent manner.
Animal experiment [2]:

Animal models

SHO male mice

Preparation Method

The in vivo xenotransplantation experiment was conducted in male SHO mice. Mice had their testicles removed under isoflurane anesthesia and were given a recovery time of 7 to 10 days. LNCaP/AR (cs) cells were suspended in 50% RPMI and 50% Matrigel. 3×106 cells were injected into each xenograft, with a volume of 100μL. Observe the animals every week until the tumor grows significantly. Forty to 60 days after injection, the animals were randomly divided into cohorts with equal average tumor burden and range (150-250mm3). In all LNCaP/AR (cs) xenotransplantation studies, ARN-509 (30mg/kg) and enzalutamide active pharmaceutical ingredients were prepared in 18% PEG-400, 1% Tween-80 and 1% povidone, and in 15% vitamin E-TPGS and 65% 0.5% w/v CMC solution, all compounds were administered by oral gavage daily. After daily administration of ARN-509 for 60 days, the tumor growth in mice was analyzed.

Dosage form

30mg/kg/day for 60 days; p.o.

Applications

ARN-509 treatment significantly suppressed tumor growth, and increased the survival rate of mice.

References:
[1]Koukourakis M I, Kakouratos C, Kalamida D, et al. Comparison of the effect of the antiandrogen apalutamide (ARN-509) versus bicalutamide on the androgen receptor pathway in prostate cancer cell lines[J]. Anti-cancer drugs, 2018, 29(4): 323-333.
[2]Joseph J D, Lu N, Qian J, et al. A clinically relevant androgen receptor mutation confers resistance to second-generation antiandrogens enzalutamide and ARN-509[J]. Cancer discovery, 2013, 3(9): 1020-1029.

Product Documents

Purity:>99.50%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
956104-40-8
Synonyms
ARN 509; ARN509; Apalutamide
Chemical Name
4-[7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide
SMILES
CNC(=O)C1=C(C=C(C=C1)N2C(=S)N(C(=O)C23CCC3)C4=CN=C(C(=C4)C(F)(F)F)C#N)F
Molecular Formula
C21H15F4N5O2S
Molecular Weight
477.43
Solubility
≥ 23.85mg/mL in DMSO
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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