ARN-509

For research use only. Not for therapeutic Use.

  • Cancer Drug Resistance
  • CAT Number: I005661
  • CAS Number: 956104-40-8
  • Molecular Formula: C21H15F4N5O2S
  • Molecular Weight: 477.43
  • Purity: 98%
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ARN-509 (Cat No.:I005661) is a next-generation androgen receptor inhibitor used in the treatment of non-metastatic castration-resistant prostate cancer (nmCRPC) and metastatic hormone-sensitive prostate cancer (mHSPC). It works by blocking the androgen receptor signaling pathway, which is essential for the growth and survival of prostate cancer cells. ARN-509 prevents androgen receptor activation by androgens, leading to decreased tumor cell proliferation. Its high specificity and potency reduce the risk of off-target effects. Apalutamide has been shown to significantly improve progression-free survival in patients, offering an effective treatment for advanced prostate cancer.


Catalog Number I005661
CAS Number 956104-40-8
Synonyms

Apalutamide; ARN509;ARN 509;

Molecular Formula C21H15F4N5O2S
Purity 98%
Target AR
Target Protein

P10275

Solubility DMSO 15 mg/mL Ethanol 5 mg/mL
Appearance Solid
Storage Dry, dark and at 2 - 8 °C for six months or -20°C for two years.
Overview of Clinical Research

Originator: University of California System<br />
Developer: Case Comprehensive Cancer Center; Dana-Farber Cancer Institute; Institut Paoli-Calmettes; Janssen Research &amp; Development; Singapore General Hospital<br />
Class: Antiandrogens; Antihormones; Antineoplastics; Aza compounds; Benzamides; Pyridines; Small molecules; Spiro compounds; Sulfhydryl compounds; Thiohydantoins<br />
Mechanism of Action: Androgen receptor antagonists; Hormone inhibitors<br />
Orphan Drug Status: No<br />
New Molecular Entity: Yes<br />

IC50 IC50: 16 nM (Androgen receptor)
IUPAC 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
InChI InChI=1S/C21H15F4N5O2S/c1-27-17(31)13-4-3-11(8-15(13)22)30-19(33)29(18(32)20(30)5-2-6-20)12-7-14(21(23,24)25)16(9-26)28-10-12/h3-4,7-8,10H,2,5-6H2,1H3,(H,27,31)
InChIKey HJBWBFZLDZWPHF-UHFFFAOYSA-N
SMILES CNC(=O)C1=C(C=C(C=C1)N2C(=S)N(C(=O)C23CCC3)C4=CC(=C(N=C4)C#N)C(F)(F)F)F
Reference

1: Rathkopf DE, Smith MR, Ryan CJ, Berry WR, Shore ND, Liu G, Higano CS, Alumkal
JJ, Hauke R, Tutrone RF, Saleh M, Chow Maneval E, Thomas S, Ricci DS, Yu MK, de
Boer CJ, Trinh A, Kheoh T, Bandekar R, Scher HI, Antonarakis ES. Androgen
receptor mutations in patients with castration-resistant prostate cancer treated
with apalutamide. Ann Oncol. 2017 Sep 1;28(9):2264-2271. doi:
10.1093/annonc/mdx283. PubMed PMID: 28633425. <br />
2: Rathkopf DE, Antonarakis ES, Shore ND, Tutrone RF, Alumkal JJ, Ryan CJ, Saleh
M, Hauke RJ, Bandekar R, Maneval EC, de Boer CJ, Yu MK, Scher HI. Safety and
Antitumor Activity of Apalutamide (ARN-509) in Metastatic Castration-Resistant
Prostate Cancer with and without Prior Abiraterone Acetate and Prednisone. Clin
Cancer Res. 2017 Jul 15;23(14):3544-3551. doi: 10.1158/1078-0432.CCR-16-2509.
Epub 2017 Feb 17. PubMed PMID: 28213364; PubMed Central PMCID: PMC5543693. <br />
3: Pang X, Wang Y, Chen Y. Design, synthesis, and biological evaluation of
deuterated apalutamide with improved pharmacokinetic profiles. Bioorg Med Chem
Lett. 2017 Jun 15;27(12):2803-2806. doi: 10.1016/j.bmcl.2017.04.071. Epub 2017
Apr 26. PubMed PMID: 28478926. <br />
4: Rexer H, Graefen M. [Phase III study for local or locally advanced prostate
cancer : Randomized, double-blind, placebo-controlled phase 3 study of
apalutamide in patients with local high-risk prostate cancer or locally advanced
prostate cancer receiving primary radiotherapy (ATLAS) – study AP 90/15 of the
AUO]. Urologe A. 2017 Feb;56(2):243-244. doi: 10.1007/s00120-017-0329-0. German.
PubMed PMID: 28144693. <br />
5: Smith MR, Antonarakis ES, Ryan CJ, Berry WR, Shore ND, Liu G, Alumkal JJ,
Higano CS, Chow Maneval E, Bandekar R, de Boer CJ, Yu MK, Rathkopf DE. 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. Eur Urol. 2016 Dec;70(6):963-970. doi:
10.1016/j.eururo.2016.04.023. Epub 2016 May 6. PubMed PMID: 27160947; PubMed
Central PMCID: PMC5568792.

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