Flutamide

Title: Flutamide
CAS Registry Number: 13311-84-7
CAS Name: 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Additional Names: a,a,a-trifluoro-2-methyl-4¢-nitro-m-propionotoluidide; 4¢-nitro-3¢-trifluoromethylisobutyranilide; niftolid
Manufacturers' Codes: Sch-13521
Trademarks: Drogenil (Schering); Eulexin (Schering); Euflex (Schering); Flucinom (Schering); Flutamin (Merck KGaA); Fugerel (Schering)
Molecular Formula: C11H11F3N2O3
Molecular Weight: 276.21
Percent Composition: C 47.83%, H 4.01%, F 20.63%, N 10.14%, O 17.38%
Literature References: Prepn: Baker et al., J. Med. Chem. 10, 93 (1967); Neri, Topliss, DE 2130450 (1972 to Sherico), C.A. 78, 58091g (1973); Gold, DE 2261293; idem, US 3847988 (1973, 1974 both to Schering). Activity studies: Neri et al., Endocrinology 91, 427 (1972); Peets et al., ibid. 94, 532 (1974); B. A. Gladue, L. G. Clemens, Endocrinology 106, 1917 (1980). Effect in prostatic cancer: P. C. Sogani, W. F. Whitmore, J. Urol. 122, 640 (1979). Clinical evaluation in pancreatic cancer: B. A. Greenway, Br. Med. J. 316, 1935 (1998).
Properties: Crystals from benzene, mp 111.5-112.5°.
Melting point: mp 111.5-112.5°
Therap-Cat: Antiandrogen; antineoplastic (hormonal).
Therap-Cat-Vet: Antiandrogen.
Keywords: Antiandrogen; Antineoplastic (Hormonal); Antiandrogens.
Fluthiacet-methyl Fluticasone Propionate Flutolanil Flutriafol Flutrimazole

Flutamide
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Systematic (IUPAC) name
2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-propanamide
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a697045
Pregnancy cat. D
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability >90%
Protein binding 94 to 96%
Excretion >90% via urine
Identifiers
CAS number 13311-84-7 YesY
ATC code L02BB01
PubChem CID 3397
DrugBank DB00499
ChemSpider 3280 YesY
UNII 76W6J0943E YesY
KEGG D00586 YesY
ChEBI CHEBI:5132 YesY
ChEMBL CHEMBL806 YesY
Chemical data
Formula C11H11F3N2O3 
Mol. mass 276.212 g/mol
 YesY (what is this?)  (verify)

Flutamide is an oral, non-steroidal antiandrogen drug primarily used to treat prostate cancer. It competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. By doing so, it prevents them from stimulating the prostate cancer cells to grow. Flutamide has been largely replaced by a newer member of this class, bicalutamide, due to a better side-effect profile. Flutamide may also be used to treat excess androgen levels in women - especially those with PolyCystic Ovarian Syndrome (PCOS).[1] It is marketed by Schering-Plough under the brand name Eulexin. It is also known as Flutamin.

It is broadly classified as an androgen receptor blocker.