They are very close to bicalutamide structurally, with the key differences being that the linker sulfone of bicalutamide has been replaced with an ether or thioether group to confer agonism of the AR and the 4-fluoro atom of the pertinent phenyl ring has been substituted with an acetamido or cyano group to eliminate reactivity at the position. A few radiolabeled derivatives of bicalutamide have been developed for potential use as radiotracers in medical imaging. They include [18F]bicalutamide, 4-[76Br]bromobicalutamide, and [76Br]bromo-thiobicalutamide. The latter two were found to have substantially increased affinity for the AR relative to that of bicautamide. However, none of these agents have been evaluated in humans.5N-Bicalutamide, or 5-azabicalutamide, is a minor structural modification of bicalutamide which acts as a reversible covalent antagonist of the AR and has approximately 150-fold higher affinity for the AR and about 20-fold greater functional inhibition of the AR relative to bicalutamide. It is among the most potent AR antagonists to have been developed and is being researched for potential use in the treatment of antiandrogen-resistant prostate cancer. Synthesis
A number of chemical syntheses of bicalutamide have been published in the literature. The procedure of the first published synthesis of bicalutamide can be seen below. History
Bicalutamide as well as all of the other currently marketed NSAAs were derived from structural modification of flutamide, which itself was originally synthesized as a bacteriostatic agent in 1967 at Schering Plough Corporation and was subsequently and serendipitously found to possess antiandrogenic activity.
Medical uses
Bicalutamide is approved for and mainly used in the following indications:
Metastatic prostate cancer (mPC) in men in combination with a gonadotropin-releasing hormone (GnRH) analogue or surgical castration at 50 mg/day
Locally advanced prostate cancer (LAPC) in men as a monotherapy at 150 mg/day (not approved for this use in the United States)In Japan, bicalutamide is uniquely used at a dosage of 80 mg/day both in combination with castration and as a monotherapy in the treatment of prostate cancer.Bicalutamide is also employed for the following off-label (non-approved) indications:

To reduce the effects of the testosterone flare at the initiation of GnRH agonist therapy in men
Androgen-dependent skin and hair conditions such as acne, seborrhea, excessive hair growth, and scalp hair loss in women as well as high testosterone levels due to polycystic ovary syndrome (PCOS) in women, at 25 to 50 mg/day generally in combination with a birth control pill
Feminizing hormone therapy for transgender women in combination with an estrogen usually at 50 mg/day
Peripheral precocious puberty in boys at 12.5 to 100 mg/day in combination with an aromatase inhibitor like anastrozole, especially for familial male-limited precocious puberty (testotoxicosis)
Overly long-lasting erections in men at 50 mg per week to 50 mg every other dayThe medication has been suggested for but has uncertain effectiveness in the following indication:

Hypersexuality and paraphilias, particularly in combination with chemical castrationFor more information on these uses, see the medical uses of bicalutamide article. Available forms
Bicalutamide is available for the treatment of prostate cancer in most developed countries, including over 80 countries worldwide.