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Bicalutamide, sold under the brand name Casodex among others, is an antiandrogen medication that is primarily used to treat prostate cancer.
Common side effects in men include breast enlargement, breast tenderness, and hot flashes.
Bicalutamide is a member of the nonsteroidal antiandrogen (NSAA) group of medications.
Bicalutamide was patented in 1982 and approved for medical use in 1995.
Contents
1 Medical uses
1.1 Available forms
2 Contraindications
3 Side effects
3.1 Comparison
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.1.1 Antiandrogenic activity
6.1.2 Other activities
6.2 Pharmacokinetics
7 Chemistry
7.1 Analogues
7.2 Synthesis
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Cost and generics
9.4 Sales and usage
9.5 Regulation
10 Research
11 Veterinary use
12 See also
13 References
14 Further reading
15 External links
Medical uses
Main article: Medical uses of bicalutamide
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 moderate doses
Locally advanced prostate cancer (LAPC) in men as a monotherapy in high doses
It can also be and is used to a lesser extent 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 at low doses, generally in combination with a birth control pill
High testosterone levels such as due to polycystic ovary syndrome (PCOS) in women
Feminizing hormone therapy for transgender women in combination with an estrogen
Early puberty in boys in moderate doses, especially for gonadotropin-independent early puberty
Overly long-lasting erections in men at low to very low doses
It has been suggested for but has uncertain effectiveness in the following indications:
Hypersexuality and paraphilias, particularly in combination with chemical castration
For 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,
Contraindications
Bicalutamide is pregnancy category X, or “contraindicated in pregnancy”, in the U.S.,
In individuals with severe, though not mild-to-moderate hepatic impairment, there is evidence that the elimination of bicalutamide is slowed, and hence, caution may be warranted in these patients as circulating levels of bicalutamide may be increased.
Side effects
Main article: Side effects of bicalutamide
v t e Major side effects of bicalutamide alone
Frequency
Class
Side effect
Very common (≥10%)
Reproductive system and breast disorders
• Breast tenderness a • Gynecomastia a
Common (≥1% and <10%) General and psychiatric disorders • Asthenia • Decreased libido • Erectile dysfunction • Hot flashes Skin and subcutaneous tissue disorders • Decreased body hair Hepato-biliary disorders • Elevated liver enzymes b Uncommon (≥0.1% and <1%) Immune system disorders • Hypersensitivity reactions, including angioedema and hives Rare (<0.1%) and unknown Respiratory, thoracic, and mediastinal disorders • Interstitial lung disease c Skin and subcutaneous tissue disorders • Sensitivity to light Hepato-biliary disorders • Liver toxicity d Footnotes and sources a = Incidence of breast changes of up to 80 to 90%. Mild-to-moderate in 90% of cases. Incidence greatly decreased in combination with castration. b = Elevated liver enzymes rarely severe and usually transient, resolving or improving with continued therapy or with discontinuation. Incidence of 3.4% relative to 1.9% for placebo in a high-dose (150 mg/day) 4,000-patient trial. c = Six case reports of interstitial lung disease published (as of 2016). Incidence of 0.01% (12 patients) in an 87,000-patient cohort. d = Six case reports of hepatotoxicity published (as of 2018). No cases in a high-dose (150 mg/day) 4,000-patient trial (suggesting incidence of <0.03%). Sources: The side effect profile of bicalutamide is highly dependent on sex; that is, on whether the person is male or female. In men, due to androgen deprivation, a variety of side effects of varying severity may occur during bicalutamide treatment, with breast pain/tenderness and gynecomastia ( breast development / enlargement ) being the most common. Bicalutamide monotherapy has been associated with abnormal liver function tests such as elevated liver enzymes in 3.4% of men relative to 1.9% for standard care. A total of 6 cases of hepatotoxicity or liver failure, two of which resulted in death, have been reported in association with bicalutamide. Comparison See also: Comparison of bicalutamide with other antiandrogens The side effect profile of bicalutamide in men and women differs from that of other antiandrogens and is considered favorable in comparison. Bicalutamide does not share the high risk of neuropsychiatric side effects like depression, anxiety, and suicidality as well as cardiovascular side effects like coagulation changes, thrombosis, fluid retention, ischemic cardiomyopathy, and adverse serum lipid changes that CPA is associated with. Overdose A single oral dose of bicalutamide in humans that results in symptoms of overdose or that is considered to be life-threatening has not been established. Interactions Bicalutamide is almost exclusively metabolized by CYP3A4. Because bicalutamide circulates at relatively high concentrations and is highly protein-bound, it has the potential to displace other highly protein-bound drugs like warfarin, phenytoin, theophylline, and aspirin from plasma binding proteins. Pharmacology Main article: Pharmacology of bicalutamide Pharmacodynamics Antiandrogenic activity Bicalutamide acts as a highly selective competitive silent antagonist of the AR ( IC 50 = 159–243 nM), the major biological target of the androgen sex hormones testosterone and DHT, and hence is an antiandrogen. The affinity of bicalutamide for the AR is relatively low as it is approximately 30 to 100 times lower than that of DHT, which is 2.5- to 10-fold as potent as an AR agonist as testosterone in bioassays and is the main endogenous ligand of the receptor in the prostate gland. Blockade of the AR by bicalutamide in the pituitary gland and hypothalamus results in prevention of the negative feedback of androgens on the hypothalamic–pituitary–gonadal axis (HPG axis) in males and consequent disinhibition of pituitary luteinizing hormone (LH) secretion. NSAA monotherapy, including with bicalutamide, shows a number of tolerability differences from methods of androgen deprivation therapy that incorporate surgical or medical castration. For example, the rates of hot flashes, depression, fatigue, and sexual dysfunction are all much higher with GnRH analogues than with NSAA monotherapy. It is thought that this is because GnRH analogues suppress estrogen production in addition to androgen production, resulting in estrogen deficiency. Under normal circumstances, bicalutamide has no capacity to activate the AR. In transgender women, breast development is a desired effect of antiandrogen or estrogen treatment. Bicalutamide monotherapy seems to have minimal effect on testicular spermatogenesis, testicular ultrastructure, and certain aspects of male fertility. Other activities Bicalutamide has been found to act as an inhibitor or inducer of certain cytochrome P450 enzymes including CYP3A4, CYP2C9, CYP2C19, and CYP2D6 in preclinical research, but no evidence of this has been found in humans treated with up to 150 mg/day. Pharmacokinetics Though its absolute bioavailability in humans is unknown, bicalutamide is known to be extensively and well- absorbed. The tissue distribution of bicalutamide is not well-characterized. Bicalutamide is metabolized in the liver. Bicalutamide is eliminated in similar proportions in feces (43%) and urine (34%), while its metabolites are eliminated roughly equally in urine and bile. The pharmacokinetics of bicalutamide are not affected by consumption of food, a person's age or body weight, renal impairment, or mild-to-moderate hepatic impairment. v t e Bicalutamide metabolism in humans Bicalutamide ( S )-Bicalutamide glucuronide ( R )-Hydroxybicalutamide ( R )-Hydroxybicalutamide glucuronide Glucuronidation via UGT1A9 Glucuronidation via UGT1A9 Hydroxylation via CYP3A4 This diagram illustrates the primary metabolic pathways involved in the metabolism of bicalutamide in humans. Chemistry Bicalutamide is a racemic mixture consisting of equal proportions of enantiomers ( R )-bicalutamide ( dextrorotatory ) and ( S )-bicalutamide ( levorotatory ). The acid dissociation constant (pKa') of bicalutamide is approximately 12. Bicalutamide is a synthetic and nonsteroidal compound which was derived from flutamide. Analogues See also: Discovery and development of antiandrogens First-generation NSAAs including bicalutamide, flutamide, and nilutamide are all synthetic, nonsteroidal anilide derivatives and structural analogues of each other. Chemical structures of first-generation NSAAs Flutamide Nilutamide Bicalutamide Topilutamide The second-generation NSAAs enzalutamide and apalutamide were derived from and are analogues of the first-generation NSAAs, Enzalutamide is a modification of bicalutamide in which the inter-ring linking chain has been altered and cyclized into a 5,5-di methyl -4- oxo -2- thioxo imidazolidine moiety. In apalutamide, the 5,5-dimethyl groups of the imidazolidine ring of enzalutamide are cyclized to form an accessory cyclobutane ring and one of its phenyl rings is replaced with a pyridine ring. Chemical structures of second-generation NSAAs Enzalutamide Apalutamide Proxalutamide Darolutamide The first nonsteroidal androgens, the arylpropionamides, were discovered via structural modification of bicalutamide. Chemical structures of arylpropionamide SARMs Acetothiolutamide Enobosarm Andarine A few radiolabeled derivatives of bicalutamide have been developed for potential use as radiotracers in medical imaging. 5 N -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. Synthesis A number of chemical syntheses of bicalutamide have been published in the literature. Bicalutamide synthesis Where the starting material is 4-cyano-3-(trifluoromethyl)aniline (also known as 4-amino-2-(trifluoromethyl)benzonitrile), DMA is dimethylacetamide, and m CPBA is meta -chloroperoxybenzoic acid. 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. Bicalutamide was first studied in a phase I clinical trial in 1987 Following its introduction for use in combination with a GnRH analogue, bicalutamide was developed as a monotherapy at a dosage of 150 mg/day for the treatment of prostate cancer, and was approved for this indication in Europe, Canada, and a number of other countries in the late 1990s and early 2000s. Subsequent to negative findings of bicalutamide monotherapy for LPC in the EPC trial, approval of bicalutamide for use specifically in the treatment of LPC was withdrawn in a number of countries The patent protection of bicalutamide expired in the U.S. in March 2009 and the drug has subsequently been available as a generic, Bicalutamide was the fourth antiandrogen (and the third NSAA ) to be introduced for the treatment of prostate cancer, following the SAA CPA in 1973 Society and culture Generic names Bicalutamide is the generic name of the drug in English and French and its INN, USAN, USP, Brand names Bicalutamide is marketed by AstraZeneca in oral tablet form under the brand names Casodex, Cosudex, Calutide, Calumid, and Kalumid in many countries. Cost and generics Bicalutamide is off-patent and available as a generic, and its cost is low in comparison to a number of other similar medications (from US$10 to US$15.44 for a 30-day supply of once-daily 50 mg tablets). The patent protection of all three of the first-generation NSAAs has expired and flutamide and bicalutamide are both available as low-cost generics. Bicalutamide is considerably less costly than GnRH analogues, which, in spite of some having been off-patent many years, have been reported (in 2013) to typically cost US$10,000–$15,000 per year (or about US$1,000 per month) of treatment. Sales and usage Sales of bicalutamide (as Casodex) worldwide peaked at US$ 1.3 billion in 2007, Worldwide sales (millions, USD ) of Casodex, 1995–2017 Year Sales Year Sales Year Sales Year Sales Year Sales Year Sales Year Sales Year Sales 1995 ~$15m 1998 $245m 2001 $569m 2004 $1012m 2007 * $1335m 2010 $579m 2013 $376m 2016 $247m 1996 $109m 1999 $340m 2002 $644m 2005 $1123m 2008 $1258m 2011 $550m 2014 $320m 2017 $215m 1997 $200m 2000 $433m 2003 $854m 2006 $1206m 2009 $844m 2012 $454m 2015 $267m 2018 ND Total sales: $13.2 billion (as of end 2017). *: First generic availability. Between January 2007 and December 2009 (a period of three years), 1,232,143 prescriptions of bicalutamide were dispensed in the U.S., or about 400,000 prescriptions per year. Regulation Bicalutamide is a prescription drug. Research Bicalutamide has been studied in combination with the 5α-reductase inhibitors finasteride and dutasteride in prostate cancer. Bicalutamide has been studied in the treatment of benign prostatic hyperplasia (BPH) in a 24-week trial of 15 patients at a dosage of 50 mg/day. A phase III clinical trial of bicalutamide in combination with an ethinylestradiol -containing combined oral contraceptive for the treatment of severe hirsutism in women with PCOS was completed in Italy in 2017 under supervision of the Italian Agency for Drugs (AIFA). Veterinary use Bicalutamide may be used to treat hyperandrogenism and associated benign prostatic hyperplasia secondary to hyperadrenocorticism (caused by excessive adrenal androgens) in male ferrets. See also Comparison of bicalutamide with other antiandrogens

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