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Flutamide, sold under the brand name Eulexin among others, is a nonsteroidal antiandrogen (NSAA) which is used primarily to treat prostate cancer.
Side effects in men include breast tenderness and enlargement, feminization, sexual dysfunction, and hot flashes. Conversely, the medication has fewer side effects and is better-tolerated in women. Diarrhea and elevated liver enzymes can occur in both sexes. Rarely, flutamide can cause liver damage, lung disease, sensitivity to light, elevated methemoglobin, elevated sulfhemoglobin, and deficient neutrophils.
Flutamide acts as a selective antagonist of the androgen receptor (AR), competing with androgens like testosterone and dihydrotestosterone (DHT) for binding to ARs in tissues like the prostate gland. By doing so, it prevents their effects and stops them from stimulating prostate cancer cells to grow. Flutamide is a prodrug to a more active form. Flutamide and its active form stay in the body for a relatively short time, which makes it necessary to take flutamide multiple times per day.
Flutamide was discovered in 1967 and was first introduced for medical use in 1983. It became available in the United States in 1989. The medication has largely been replaced by newer and improved NSAAs, namely bicalutamide and enzalutamide, due to their better efficacy, tolerability, safety, and dosing frequency (once per day), and is now relatively little-used.
Contents
1 Medical uses
1.1 Prostate cancer
1.2 Skin and hair conditions
1.2.1 Acne and seborrhea
1.2.2 Excessive hair growth
1.2.3 Scalp hair loss
1.3 Transgender hormone therapy
1.4 Available forms
2 Side effects
2.1 Gynecomastia
2.2 Diarrhea
2.3 Rare reactions
2.3.1 Liver toxicity
2.3.2 Others
3 Pharmacology
3.1 Pharmacodynamics
3.1.1 Antiandrogenic activity
3.1.2 CYP17A1 inhibition
3.1.3 Other activities
3.2 Pharmacokinetics
4 Chemistry
4.1 Synthesis
5 History
6 Society and culture
6.1 Generic names
6.2 Brand names
6.3 Availability
7 Research
7.1 Enlarged prostate
7.2 Bulimia nervosa
8 References
9 Further reading
Medical uses
Prostate cancer
GnRH is released by the hypothalamus in a pulsatile fashion; this causes the anterior pituitary gland to release luteinizing hormone (LH) and follicle-stimulating hormone (FSH). LH stimulates the testes to produce testosterone, which is metabolized to DHT by the enzyme 5α-reductase.
DHT, and to a significantly smaller extent, testosterone, stimulate prostate cancer cells to grow. Therefore, blocking these androgens can provide powerful treatment for prostate cancer, especially metastatic disease. Normally administered are GnRH analogues, such as leuprorelin or cetrorelix. Although GnRH agonists stimulate the same receptors that GnRH does, since they are present continuously and not in a pulsatile manner, they serve to inhibit the pituitary gland and therefore block the whole chain. However, they initially cause a surge in activity; this is not solely a theoretical risk but may cause the cancer to flare. Flutamide was initially used at the beginning of GnRH agonist therapy to block this surge, and it and other NSAAs continue in this use. In contrast to GnRH agonists, GnRH antagonists don’t cause an initial androgen surge, and are gradually replacing GnRH agonists in clinical use.
There have been studies to investigate the benefit of adding an antiandrogen to surgical orchiectomy or its continued use with a GnRH analogue ( combined androgen blockade (CAB)). Adding antiandrogens to orchiectomy showed no benefit, while a small benefit was shown with adding antiandrogens to GnRH analogues.
Unfortunately, therapies which lower testosterone levels, such as orchiectomy or GnRH analogue administration, also have significant side effects. Compared to these therapies, treatment with antiandrogens exhibits “fewer hot flashes, less of an effect on libido, less muscle wasting, fewer personality changes, and less bone loss.” However, antiandrogen therapy alone is less effective than surgery. Nevertheless, given the advanced age of many with prostate cancer, as well as other features, many men may choose antiandrogen therapy alone for a better quality of life.
Flutamide has been found to be similarly effective in the treatment of prostate cancer to bicalutamide, although indications of inferior efficacy, including greater compensatory increases in testosterone levels and greater reductions in PSA levels with bicalutamide, were observed.
A dosage of 750 mg/day flutamide (250 mg/three times a day) is roughly equivalent in terms of effectiveness to 50 mg/day bicalutamide when used as the antiandrogen component in combined androgen blockade in the treatment of advanced prostate cancer.
Flutamide has been used to prevent the effects of the testosterone flare at the start of GnRH agonist therapy in men with prostate cancer.
Skin and hair conditions
Flutamide has been researched and used extensively in the treatment of androgen-dependent skin and hair conditions in women including acne, seborrhea, hirsutism, and scalp hair loss, as well as in hyperandrogenism (e.g., in polycystic ovary syndrome or congenital adrenal hyperplasia ), and is effective in improving the symptoms of these conditions. The dosages used are lower than those used in the treatment of prostate cancer. Although flutamide continues to be used for these indications, its use in recent years has been limited due to the risk of potentially fatal hepatotoxicity, and it is no longer recommended as a first- or second-line therapy.
Acne and seborrhea
Flutamide has been found to be effective in the treatment of acne and seborrhea in women in a number of studies.
Excessive hair growth
Flutamide has been found to be effective in the treatment of hirsutism (excessive body / facial growth) in numerous studies.
Scalp hair loss
Flutamide has been found to be effective in the treatment of female pattern hair loss in a number of studies.
Transgender hormone therapy
Flutamide has been used as a component of feminizing hormone therapy for transgender women.
Available forms
Flutamide is available in the form of 125 mg oral capsules and 250 mg oral tablets.
Side effects
The side effects of flutamide are sex -dependent. In men, a variety of side effects related to androgen deprivation may occur, the most common being gynecomastia and breast tenderness.
v t e Side effects of combined androgen blockade with flutamide
Side effect
Flutamide 750 mg/day a + GnRH agonist (n = 294) (%) b,c
Placebo + GnRH agonist (n = 285) (%) b,c
Hot flashes
61
57
Decreased libido
36
31
Erectile dysfunction
33
29
Diarrhea
12
4
  Severe
4
<1 Nausea / vomiting 11 10 Gynecomastia 9 11 Others 7 9 Other gastrointestinal disorders 6 4 Anemia 6 ND Footnotes: a = 250 mg three times per day at 8-hour intervals. b = Phase III studies of combined androgen blockade (flutamide + GnRH agonist ) in men with advanced prostate cancer. c = Incidence ≥5% regardless of causality. Sources: v t e Side effects of combined androgen blockade with nonsteroidal antiandrogens Side effect Bicalutamide 50 mg/day + GnRH agonist (n = 401) (%) a,b Flutamide 750 mg/day c + GnRH agonist (n = 407) (%) a,b Hot flashes 52.6 53.3 Pain (general) 35.4 31.2 Back pain 25.4 25.8 Asthenia 22.2 21.4 Constipation 21.7 17.0 Pelvic pain 21.2 17.2 Infection 17.7 14.0 Nausea 14.0 13.6 Peripheral edema 13.2 10.3 Anemia d 12.7 14.7 Dyspnea 12.7 7.9 Diarrhea 12.2 26.3 Nocturia 12.2 13.5 Hematuria 12.0 6.4 Abdominal pain 11.3 11.3 Dizziness 10.2 8.6 Bone pain 9.2 10.6 Gynecomastia 9.0 7.4 Rash 8.7 7.4 Urinary tract infection 8.7 8.8 Chest pain 8.5 8.4 Hypertension 8.5 7.1 Coughing 8.2 5.9 Pharyngitis 8.0 5.7 Paresthesia 7.7 9.8 Elevated liver enzymes e 7.5 11.3    Markedly elevated f 0.5 2.5 Weight loss 7.5 9.6 Headache 7.2 6.6 Flu-like symptoms 7.0 4.9 Myasthenia 6.7 4.7 Insomnia 6.7 9.6 Erectile dysfunction 6.7 8.6 Flatulence 6.5 5.4 Hyperglycemia 6.5 6.6 Dyspepsia 6.5 5.7 Decreased appetite 6.2 7.1 Sweating 6.2 4.9 Bronchitis 6.0 2.7 Breast pain/tenderness 5.7 3.7 Urinary frequency 5.7 7.1 Elevated alkaline phosphatase 5.5 5.9 Weight gain 5.5 4.4 Arthritis 5.2 7.1 Anxiety 5.0 2.2 Urinary retention 5.0 3.4 Urinary impairment 4.7 3.7 Pneumonia 4.5 4.7 Pathological fracture 4.2 7.9 Depression 4.0 8.1 Vomiting 4.0 6.9 Rhinitis 3.7 5.4 Urinary incontinence 3.7 7.9 Footnotes: a = Phase III studies of combined androgen blockade ( bicalutamide or flutamide + GnRH agonist ) in men with advanced prostate cancer. b = Incidence >5% regardless of causality. c = 250 mg three times per day at 8-hour intervals. d = Anemia includes hypochromic anemia and iron deficiency anemia. e = Abnormal liver function tests reported as adverse events. f = Elevated >5 times the normal upper limit.
Gynecomastia
Flutamide, as a monotherapy, causes gynecomastia in 30 to 79% of men, and also produces breast tenderness.
Diarrhea
Diarrhea is more common and sometimes more severe with flutamide than with other NSAAs.
Rare reactions
Liver toxicity
Although rare, flutamide has been associated with severe hepatotoxicity and death.
The mechanism of action of flutamide-induced hepatotoxicity is thought to be due to mitochondrial toxicity.
The hepatotoxicity of flutamide appears to depend on hydrolysis of flutamide catalyzed by an arylacetamide deacetalyse enzyme.
Others
Flutamide has also been associated with interstitial pneumonitis (which can progress to pulmonary fibrosis ).
Out of the available EDCs looked at, flutamide has a notable effect on anogenital distance in the rats. )
Pharmacology
Pharmacodynamics
Hydroxyflutamide, the active form of flutamide.
Antiandrogenic activity
v t e Affinities of selected androgen receptor ligands
Compound
AR RBA (%)
Metribolone
100
Dihydrotestosterone
85
Cyproterone acetate
7.8
Bicalutamide
1.4
Nilutamide
0.9
Hydroxyflutamide
0.57
Flutamide
<0.0057 Flutamide acts as a selective, competitive, silent antagonist of the androgen receptor (AR). Flutamide has been found to be equal to slightly more potent than cyproterone acetate and substantially more potent than spironolactone as an antiandrogen in bioassays. v t e Plasma levels and binding potential of flutamide and bicalutamide during first week Day Total levels (ng/mL) Free levels (ng/mL) Ratios Bicalutamide Flutamide a Bicalutamide Flutamide a Free Binding potential b 1 901 940 36.0 66 0.55 2.18 2 1613 1500 64.5 105 0.61 2.46 3 2345 1500 93.8 105 0.89 3.57 4 2969 1500 118.8 105 1.13 4.53 7 4259 1500 170.4 105 1.62 6.49 Notes: During first week of treatment. Dosages not provided. Footnotes: a = As 2-hydroxyflutamide (the active form of flutamide). b = Assumes, on the basis of ligand binding assays, that bicalutamide possesses 4-fold greater affinity for the androgen receptor than 2-hydroxyflutamide. Source: CYP17A1 inhibition Flutamide and hydroxyflutamide have been found in vitro to inhibit CYP17A1 (17α-hydroxylase/17,20-lyase), an enzyme which is required for the biosynthesis of androgens. Other activities Flutamide has been identified as an agonist of the aryl hydrocarbon receptor. Pharmacokinetics The absorption of flutamide is complete upon oral ingestion. Flutamide and hydroxyflutamide have elimination half-lives of 4.7 hours and 6 hours in adults, respectively. Chemistry Unlike the hormones with which it competes, flutamide is not a steroid ; rather, it is a substituted anilide. Hence, it is described as nonsteroidal in order to distinguish it from older steroidal antiandrogens such as cyproterone acetate and megestrol acetate. Synthesis Flutamide synthesis. Schering, DE 2130450   DE 2261293   U.S. Patent 3,847,988 U.S. Patent 4,144,270 History Flutamide was first synthesized in 1967 by Neri and colleagues at Schering Plough Corporation. Society and culture Generic names Flutamide is the generic name of the drug and its INN, USAN, BAN, DCF, and JAN. Brand names Brand names of flutamide include or have included Cebatrol, Cytomid, Drogenil, Etaconil, Eulexin, Flucinom, Flumid, Flutacan, Flutamid, Flutamida, Flutamin, Flutan, Flutaplex, Flutasin, Fugerel, Profamid, and Sebatrol, among others. Availability Flutamide is marketed widely throughout the world, including in the United States, Canada, Europe, Australia, New Zealand, South Africa, Central and South America, East and Southeast Asia, India, and the Middle East. Research Enlarged prostate Flutamide has been studied in the treatment of benign prostatic hyperplasia (BPH; enlarged prostate) in men in several clinical studies. Bulimia nervosa Flutamide has been studied in the treatment of bulimia nervosa in women.

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