Apalutamide

Apalutamide
Clinical data
Trade names	Erleada, others
Other names	ARN-509; JNJ-56021927; JNJ-927; A52
AHFS/Drugs.com	Monograph
MedlinePlus	a618018
License data	US DailyMed: Erleada;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
Drug class	Nonsteroidal antiandrogen
ATC code	L02BB05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100%
Protein binding	Apalutamide: 96%; NDMA: 95%
Metabolism	Liver (CYP2C8, CYP3A4)
Metabolites	• NDMATooltip N-Desmethylapalutamide
Elimination half-life	Apalutamide: 3–4 days (at steady-state)
Excretion	Urine: 65%; Feces: 24%
Identifiers
	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;
CAS Number	956104-40-8; 1361232-32-7;
PubChem CID	24872560;
DrugBank	DB11901;
ChemSpider	28424131;
UNII	4T36H88UA7;
KEGG	D11040;
ChEMBL	ChEMBL3183409;
CompTox Dashboard (EPA)	DTXSID40241899 ;
ECHA InfoCard	100.235.115
Chemical and physical data
Formula	C21H15F4N5O2S
Molar mass	477.44 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	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); Key:HJBWBFZLDZWPHF-UHFFFAOYSA-N;

Apalutamide, sold under the brand name Erleada among others, is a nonsteroidal antiandrogen (NSAA) medication used for the treatment of prostate cancer. It is an androgen receptor inhibitor. It is taken by mouth.

Side effects of apalutamide when added to castration include fatigue, nausea, abdominal pain, diarrhea, high blood pressure, rash, falls, bone fractures, and an underactive thyroid. Rarely, it can cause seizures. The medication has a high potential for drug interactions. Apalutamide is an antiandrogen, and acts as an antagonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone. In doing so, it prevents the effects of these hormones in the prostate gland and elsewhere in the body.

Apalutamide was first described in 2007, and was approved for the treatment of prostate cancer in February 2018. It is the first medication to be approved specifically for the treatment of non-metastatic castration-resistant prostate cancer.