Enzalutamide

Enzalutamide
Clinical data
Trade names	Xtandi
Other names	MDV-3100; ASP-9785
AHFS/Drugs.com	Monograph
MedlinePlus	a612033
License data	EU EMA: by INN; US DailyMed: Enzalutamide; US FDA: Enzalutamide;
Pregnancy; category	AU: X (High risk);
Routes of; administration	By mouth (capsules)
Drug class	Nonsteroidal antiandrogen
ATC code	L02BB04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	Rats: 89.7%; Humans: unknown (but at least 84.6% based on recovery from excretion)
Protein binding	Enzalutamide: 97–98% (primarily to albumin); NDME: 95%
Metabolism	Liver (primarily CYP2C8 and CYP3A4)
Metabolites	• NDMETooltip N-Desmethylenzalutamide (active); • Carboxylic acid derivative metabolite (inactive)
Elimination half-life	Enzalutamide: 5.8 days (range 2.8–10.2 days); NDME: 7.8–8.6 days
Excretion	Urine: 71.0%; Bile: 13.6%; Feces: 0.39%
Identifiers
	IUPAC name 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide;
CAS Number	915087-33-1;
PubChem CID	15951529;
IUPHAR/BPS	6812;
DrugBank	DB08899;
ChemSpider	13093347;
UNII	93T0T9GKNU;
KEGG	D10218;
ChEBI	CHEBI:68534 ;
ChEMBL	ChEMBL1082407;
CompTox Dashboard (EPA)	DTXSID10912307 ;
ECHA InfoCard	100.231.722
Chemical and physical data
Formula	C21H16F4N4O2S
Molar mass	464.44 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNC(=O)c1ccc(N2C(=S)N(c3ccc(C#N)c(C(F)(F)F)c3)C(=O)C2(C)C)cc1F;
	InChI InChI=1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-4-11(10-26)15(8-12)21(23,24)25)19(32)29(20)13-6-7-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30); Key:WXCXUHSOUPDCQV-UHFFFAOYSA-N;

Enzalutamide, sold under the brand name Xtandi, is a nonsteroidal antiandrogen (NSAA) medication which is used in the treatment of prostate cancer. It is indicated for use in conjunction with castration in the treatment of metastatic castration-resistant prostate cancer (mCRPC), nonmetastatic castration-resistant prostate cancer, and metastatic castration-sensitive prostate cancer (mCSPC). It is taken by mouth.

Side effects of enzalutamide when added to castration include asthenia, back pain, diarrhea, arthralgia, and hot flashes. Rarely, it can cause seizures. It has a high potential for drug interactions. Enzalutamide 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.

Enzalutamide was first described in 2006, and was introduced for the treatment of prostate cancer in 2012. It was the first second-generation NSAA to be introduced. It is on the World Health Organization's List of Essential Medicines.

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