T3D4818

4873 T3D4818

Bicalutamide

Bicalutamide is an oral non-steroidal anti-androgen for prostate cancer. It binds to the androgen receptor. 90357-06-5

2375

C18H14F4N2O4S

White powder.

191-193°C

5 mg/L

Bicalutamide is well-absorbed following oral administration, although the absolute bioavailability is unknown.

Bicalutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin which stimulate the growth of normal and malignant prostatic tissue. Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Bicalutamide undergoes stereo specific metabolism. The S (inactive) isomer is metabolized primarily by glucuronidation. The R (active) isomer also undergoes glucuronidation but is predominantly oxidized to an inactive metabolite followed by glucuronidation. Half Life: 5.9 days No indication of carcinogenicity to humans (not listed by IARC).

For treatment (together with surgery or LHRH analogue) of advanced prostatic cancer.

2014-09-11T05:17:56Z

2014-12-24T20:26:57Z

Bicalutamide

C08160

100717

C053541

DB01128

true

CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(O)=NC1=CC(=C(C=C1)C#N)C(F)(F)F

C18H14F4N2O4S

InChI=1/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)

InChIKey=LKJPYSCBVHEWIU-UHFFFAOYNA-N

430.373

430.061040456

Exogenous Solid 2.5

HMDB15260

CHEMBL409

50614

Nnochiri Ekwuribe, “METHODS OF SYNTHESIZING ACYLANILIDES INCLUDING BICALUTAMIDE AND DERIVATIVES THEREOF.” U.S. Patent US20020165406, issued November 07, 2002.