Flutamide

Structural formula
General
Non-proprietary name	Flutamide
other names	2-methyl- N - [4-nitro-3- (trifluoromethyl) phenyl] propionic acid amide; 4-nitro-3- (trifluoromethyl) isobutyranilide; N - (4-nitro-3-trifluoromethylphenyl) isobutyramide ( IUPAC ) ; Flutamidum ( Latin ) ;
Molecular formula	C 11 H 11 F 3 N 2 O 3
Brief description	pale yellow crystalline powder
External identifiers / databases
EC number	236-341-9
ECHA InfoCard	100.033.024
PubChem	3397
DrugBank	DB00499
Wikidata	Q418669
Drug information
ATC code	L02 BB01
Drug class	Cytostatic, nonsteroidal antiandrogens
properties
Molar mass	276.21 g mol −1
Physical state	firmly
Melting point	111.5-112.5 ° C
solubility	practically insoluble in water, easily soluble in acetone and ethanol
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-312-332-361
	P: 280
Toxicological data	787 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Flutamide is a drug from the group of cytostatics that is used in the treatment of advanced prostate cancer . Flutamide belongs to the class of anti- androgens .

Clinical information

Indications / possible uses

Palliative treatment of advanced prostate cancer in untreated or hormone refractory patients. Adjuvant therapy of localized prostate cancer (stage B2-C) in combination with an LHRH - agonist and appropriate radiotherapy.

Contraindications (contraindications)

Hypersensitivity to the active ingredient flutamide. Flutamide is not intended for use in fertile men without reliable contraception and in women and children.

Pharmacological properties

Absorption and distribution in the body (pharmacokinetics)

Absorption : After oral administration, flutamide is rapidly and completely absorbed. Mean flutamidepeakplasma concentrationsof 92-113 ng / ml are measured 1.3-1.5 hours after administration of 250 mg flutamide. Mean peak plasma concentrations of the main active metabolite 2-hydroxyflutamide of 894 ng / ml are measured 2.7 hours after ingestion of 250 mg of the drug. Steady-state - plasma concentrations are achieved for both substances after 5 days. Ingestion of food has no influence on bioavailability . Distribution : No data are available on the volume of distribution. The plasma protein binding of flutamide is 94–96%, that of the active metabolite 92–94%. Metabolism : Flutamide is rapidly and extensively metabolized . 10 metabolites are identified. The main metabolite is the active 2-hydroxyflutamide, which is mainly formed via CYP 1A2 . Elimination : The plasma half-lives are 7.8 hours for flutamide and 8.1 hours for 2-hydroxyflutamide. Flutamide is mainly excreted renally in the form of metabolites. Only small amounts of the substance are excretedwith the faeces . ${\ displaystyle C _ {\ mathrm {max}}}$

Other Information

Flutamide was patented by Schering in 1973 and is commercially available as a generic .

literature

W. Forth, D. Henschler, W. Rummel: General and special pharmacology and toxicology . 9th edition. URBAN & FISCHER, Munich 2005, ISBN 3-437-42521-8 .

Individual evidence

↑ ^a ^b ^c data sheet FLUTAMIDE CRS (PDF) at EDQM , accessed April 2008.

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 720, ISBN 978-0-911910-00-1 .

↑ ^a ^b Flutamide data sheet from Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).

Trade names

Monopreparations

Flucinorm (CH), Flumid (D), Fugerel (D, A), Prostakonyl (A), Prostica (D), various generics (D, A)

Web links

Eulexin (flutamide) capsule (Schering Corporation) from Dailymed as of May 2006

[Ph._Eur.-1] ta sheet FLUTAMIDE CRS (PDF) at EDQM , accessed April 2008.

[MerckIndex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 720, ISBN 978-0-911910-00-1 .