Flutamide

Flutamide
Clinical data


Trade names	Eulexin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a697045
Pregnancy category	D
Routes of administration	By mouth
ATC code	L02BB01 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	>90%
Protein binding	94 to 96%
Biological half-life	8 hours (for 2-hydroxyflutamide)
Excretion	>90% via urine
Identifiers
IUPAC name 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Synonyms	Niftolide; SCH-13521; 4'-nitro-3'-trifluoromethylisobutyranilide
CAS Number	13311-84-7^Y
PubChem (CID)	3397
IUPHAR/BPS	6943
DrugBank	DB00499^Y
ChemSpider	3280^Y
UNII	76W6J0943E^Y
KEGG	D00586^Y
ChEBI	CHEBI:5132^Y
ChEMBL	CHEMBL806^Y
ECHA InfoCard	100.033.024
Chemical and physical data
Formula	C₁₁H₁₁F₃N₂O₃
Molar mass	276.212 g/mol
3D model (Jmol)	Interactive image
Melting point	111.5 to 112.5 °C (232.7 to 234.5 °F)
SMILES O=C(Nc1cc(c(cc1)[N+]([O-])=O)C(F)(F)F)C(C)C
InChI InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)^Y Key:MKXKFYHWDHIYRV-UHFFFAOYSA-N^Y

Flutamide, sold under the brand name Eulexin among others, is a synthetic, non-steroidal antiandrogen (NSAA) used primarily to treat prostate cancer. It acts as a selective antagonist of the androgen receptor (AR), competing with androgens such as testosterone and its powerful active metabolite dihydrotestosterone (DHT) for binding to ARs in the prostate gland. By doing so, it prevents them from stimulating the prostate cancer cells to grow. In addition to its use in prostate cancer, flutamide has been used to treat hyperandrogenism (excess androgen levels) in women, such as in those with polycystic ovary syndrome (PCOS), and hirsutism. Flutamide has been largely replaced by newer NSAAs, namely bicalutamide and enzalutamide, due particularly to better safety, tolerability, and pharmacokinetic profiles.

GnRH is released by the hypothalamus in a pulsatile fashion; this causes the anterior pituitary gland to release luteinizing hormone (LH) and follicle-stimulating hormone (FSH). LH stimulates the testes to produce testosterone, which is metabolized to DHT by the enzyme 5α-reductase.