apalutamide   Click here for help

GtoPdb Ligand ID: 9043

Synonyms: ARN-509 | ARN509 | Erleada® | JNJ-56021927
Approved drug
apalutamide is an approved drug (FDA (2018), EMA (2019))
Compound class: Synthetic organic
Comment: Apalutamide is a novel androgen receptor (AR) antagonist (antiandrogen) that is approved as a treatment for castration-resistant prostate cancer (CRPC) [3]. This compound (91) was discovered in a structure/activity relationship-guided medicinal chemistry program designed to identify antiandrogens devoid of agonistic activity in the setting of androgen receptor overexpression [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 121.42
Molecular weight 477.09
XLogP 2.86
No. Lipinski's rules broken 0
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Canonical SMILES CNC(=O)c1ccc(cc1F)N1C(=S)N(C(=O)C21CCC2)c1cnc(c(c1)C(F)(F)F)C#N
Isomeric SMILES CNC(=O)c1ccc(cc1F)N1C(=S)N(C(=O)C21CCC2)c1cnc(c(c1)C(F)(F)F)C#N
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)
1. Jung ME, Ouk S, Yoo D, Sawyers CL, Chen C, Tran C, Wongvipat J. (2010)
Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC).
J Med Chem, 53 (7): 2779-96. [PMID:20218717]
2. Moilanen AM, Riikonen R, Oksala R, Ravanti L, Aho E, Wohlfahrt G, Nykänen PS, Törmäkangas OP, Palvimo JJ, Kallio PJ. (2015)
Discovery of ODM-201, a new-generation androgen receptor inhibitor targeting resistance mechanisms to androgen signaling-directed prostate cancer therapies.
Sci Rep, 5: 12007. [PMID:26137992]
3. Rathkopf DE, Morris MJ, Fox JJ, Danila DC, Slovin SF, Hager JH, Rix PJ, Chow Maneval E, Chen I, Gönen M et al.. (2013)
Phase I study of ARN-509, a novel antiandrogen, in the treatment of castration-resistant prostate cancer.
J Clin Oncol, 31 (28): 3525-30. [PMID:24002508]
4. Smith MR, Saad F, Chowdhury S, Oudard S, Hadaschik BA, Graff JN, Olmos D, Mainwaring PN, Lee JY, Uemura H et al.. (2018)
Apalutamide Treatment and Metastasis-free Survival in Prostate Cancer.
N Engl J Med, 378 (15): 1408-1418. [PMID:29420164]