bicalutamideとは？ わかりやすく解説

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ビカルタミド

分子式：C18H14F4N2O4S
その他の名称：Casodex、カソデックス、ICI-176334、ビカルタミド、Bicalutamide
体系名： rac-(2R*)-N-[4-シアノ-3-(トリフルオロメチル)フェニル]-3-[(4-フルオロフェニル)スルホニル]-2-ヒドロキシ-2-メチルプロパンアミド、rac-(R*)-N-[4-シアノ-3-(トリフルオロメチル)フェニル]-3-[(4-フルオロフェニル)スルホニル]-2-ヒドロキシ-2-メチルプロパンアミド

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ビカルタミド

【仮名】びかるたみど
【原文】bicalutamide

抗アンドロゲンに属する抗がん剤である。

ウィキペディア
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ウィキペディアウィキペディア

ビカルタミド

(bicalutamide から転送)

出典: フリー百科事典『ウィキペディア（Wikipedia）』 (2024/04/11 07:30 UTC 版)

ビカルタミド（Bicalutamide）は、カソデックス（Casodex）など商品名で販売されている主に前立腺癌の治療に用いられる抗アンドロゲン薬である[8]。通常、ゴナドトロピン放出ホルモン（GnRH）アナログまたは睾丸摘出手術と併用して進行性前立腺癌の治療に用いられる[8][9][10]。ビカルタミドは、女性の過度の発毛[11]、トランスジェンダーの女性の女性化ホルモン療法の構成要素[12]、男児の思春期早発症の治療[13]、男性の持続勃起症の予防にも用いられる[14]。投与法は経口である[8]。


出典
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  120. ^ “Testosterone/bicalutamide antagonism at the predicted extracellular androgen binding site of ZIP9”. Biochim. Biophys. Acta 1864 (12): 2402–2414. (2017). doi:10.1016/j.bbamcr.2017.09.012. PMID 28943399. 
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  128. ^ “Exploratory study of drug plasma levels during bicalutamide 150 mg therapy co-administered with tamoxifen or anastrozole for prophylaxis of gynecomastia and breast pain in men with prostate cancer”. Cancer Chemotherapy and Pharmacology 56 (4): 415–20. (2005). doi:10.1007/s00280-005-1016-1. PMID 15838655. https://www.researchgate.net/publication/7897958. 
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  135. ^ Wein, Alan J.; Kavoussi, Louis R.; Novick, Andrew C.; Partin, Alan W.; Peters, Craig A. (25 August 2011). Campbell-Walsh Urology: Expert Consult Premium Edition: Enhanced Online Features and Print, 4-Volume Set. Elsevier Health Sciences. pp. 2938–2939, 2946. ISBN 978-1-4160-6911-9. オリジナルの5 May 2016時点におけるアーカイブ。. https://web.archive.org/web/20160505225217/https://books.google.com/books?id=fu3BBwAAQBAJ&pg=PA2939 
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  137. ^ a b Carrell, Douglas T.; Peterson, C. Matthew (23 March 2010). Reproductive Endocrinology and Infertility: Integrating Modern Clinical and Laboratory Practice. Springer Science & Business Media. pp. 163–. ISBN 978-1-4419-1436-1. オリジナルの4 July 2014時点におけるアーカイブ。. https://web.archive.org/web/20140704201613/http://books.google.com/books?id=lcBEheiufVcC&pg=PA163 
  138. ^ a b Bouchard, P.; Caraty, A. (15 November 1993). GnRH, GnRH Analogs, Gonadotropins and Gonadal Peptides. CRC Press. pp. 455–456. ISBN 978-0-203-09205-7. https://books.google.com/books?id=uctURfWwTb4C&pg=PA455. "[...] when male levels of androgens are achieved in plasma, their effects on gonadotropin secretion are similar in women and men. [...] administration of flutamide in a group of normally-cycling women produced a clinical improvement of acne and hirsutism without any significant hormonal change. [...] All these data emphasize that physiological levels of androgens have no action on the regulation of gonadotropins in normal women. [...] Androgens do not directly play a role in gonadotropin regulation [in women]." 
  139. ^ “Treatment of bicalutamide-induced breast events”. Expert Review of Anticancer Therapy 7 (12): 1773–9. (December 2007). doi:10.1586/14737140.7.12.1773. PMID 18062751. 
  140. ^ Shlomo Melmed (1 January 2016). Williams Textbook of Endocrinology. Elsevier Health Sciences. pp. 752–. ISBN 978-0-323-29738-7. https://books.google.com/books?id=YZ8_CwAAQBAJ&pg=PA752. "GnRH analogues, both agonists and antagonists, severely suppress endogenous gonadotropin and testosterone production [...] Administration of GnRH agonists (e.g., leuprolide, goserelin) produces an initial stimulation of gonadotropin and testosterone secretion (known as a "flare"), which is followed in 1 to 2 weeks by GnRH receptor downregulation and marked suppression of gonadotropins and testosterone to castration levels. [...] To prevent the potential complications associated with the testosterone flare, AR antagonists (e.g., bicalutamide) are usually coadministered with a GnRH agonist for men with metastatic prostate cancer.399" 
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  144. ^ a b “Preliminary study with bicalutamide in heterosexual and homosexual patients with prostate cancer: a possible implication of androgens in male homosexual arousal”. BJU International 108 (1): 110–5. (July 2011). doi:10.1111/j.1464-410X.2010.09764.x. PMID 20955264. 
  145. ^ a b “The effect of estrogen on the sexual interest of castrated males: Implications to prostate cancer patients on androgen-deprivation therapy”. Critical Reviews in Oncology/Hematology 87 (3): 224–38. (September 2013). doi:10.1016/j.critrevonc.2013.01.006. PMID 23484454. 
  146. ^ “Emerging roles for neurosteroids in sexual behavior and function”. Journal of Andrology 29 (5): 524–33. (2008). doi:10.2164/jandrol.108.005660. PMID 18567641. 
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  148. ^ “The testosterone metabolite 3α-diol enhances female rat sexual motivation when infused in the nucleus accumbens shell”. The Journal of Sexual Medicine 7 (11): 3598–609. (November 2010). doi:10.1111/j.1743-6109.2010.01937.x. PMC 4360968. PMID 20646182. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4360968/. 
  149. ^ Chedrese, P. Jorge (13 June 2009). Reproductive Endocrinology: A Molecular Approach. Springer Science & Business Media. pp. 233–. ISBN 978-0-387-88186-7. オリジナルの5 September 2017時点におけるアーカイブ。. https://web.archive.org/web/20170905040216/https://books.google.com/books?id=3FJXUN6Vh44C 
  150. ^ “3alpha-androstanediol, but not testosterone, attenuates age-related decrements in cognitive, anxiety, and depressive behavior of male rats”. Frontiers in Aging Neuroscience 2: 15. (2010). doi:10.3389/fnagi.2010.00015. PMC 2874398. PMID 20552051. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874398/. 
  151. ^ “An estrogenic effect of 5alpha-androstane-3beta, 17beta-diol on the behavioral response to stress and on CRH regulation”. Neuropharmacology 54 (8): 1233–8. (June 2008). doi:10.1016/j.neuropharm.2008.03.016. PMID 18457850. 
  152. ^ “Androgens with activity at estrogen receptor beta have anxiolytic and cognitive-enhancing effects in male rats and mice”. Hormones and Behavior 54 (5): 726–34. (November 2008). doi:10.1016/j.yhbeh.2008.07.013. PMC 3623974. PMID 18775724. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3623974/. 
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  154. ^ “Novel and next-generation androgen receptor-directed therapies for prostate cancer: Beyond abiraterone and enzalutamide”. Urologic Oncology 34 (8): 348–55. (August 2016). doi:10.1016/j.urolonc.2015.05.025. PMID 26162486. 
  155. ^ a b “Beyond abiraterone: new hormonal therapies for metastatic castration-resistant prostate cancer”. Cancer Biology & Therapy 15 (2): 149–55. (February 2014). doi:10.4161/cbt.26724. PMC 3928129. PMID 24100689. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3928129/. 
  156. ^ Mulhall, John P. (21 February 2013). Fertility Preservation in Male Cancer Patients. Cambridge University Press. pp. 84–. ISBN 978-1-139-61952-3. オリジナルの29 April 2016時点におけるアーカイブ。. https://web.archive.org/web/20160429171718/https://books.google.com/books?id=97wgAwAAQBAJ&pg=PA84 
  157. ^ “Effects of long-term treatment with the anti-androgen bicalutamide on human testis: an ultrastructural and morphometric study”. Histopathology 38 (3): 195–201. (March 2001). doi:10.1046/j.1365-2559.2001.01077.x. PMID 11260298. 
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  159. ^ a b Nieschlag, Eberhard; Behre, Hermann M. (6 December 2012). Testosterone: Action – Deficiency – Substitution. Springer Science & Business Media. pp. 130, 276. ISBN 978-3-642-72185-4. https://books.google.com/books?id=jn3nCAAAQBAJ&pg=PA276 
  160. ^ a b Cheng, C.Y. (24 October 2009). Molecular Mechanisms in Spermatogenesis. Springer Science & Business Media. pp. 258–. ISBN 978-0-387-09597-4. https://books.google.com/books?id=tdpVNN80_r0C&pg=PA258 
  161. ^ Neumann, F.; Schenck, B. (1980). “Antiandrogens: Basic Concepts and Clinical Trials”. Regulation of Male Fertility. pp. 93–106. doi:10.1007/978-94-009-8875-0_10. ISBN 978-94-009-8877-4. https://books.google.com/books?id=AXArBgAAQBAJ&pg=PA93 
  162. ^ a b Johnson, Leonard R. (14 October 2003). Essential Medical Physiology. Academic Press. pp. 731–. ISBN 978-0-08-047270-6. オリジナルの15 February 2017時点におけるアーカイブ。. https://web.archive.org/web/20170215093206/https://books.google.com/books?id=Ql10m-_q3nMC&pg=PA731 
  163. ^ a b Jones, C. A.; Reiter, L.; Greenblatt, E. (2016). “Fertility preservation in transgender patients”. International Journal of Transgenderism 17 (2): 76–82. doi:10.1080/15532739.2016.1153992. ISSN 1553-2739. "Traditionally, patients have been advised to cryopreserve sperm prior to starting cross-sex hormone therapy as there is a potential for a decline in sperm motility with high-dose estrogen therapy over time (Lubbert et al., 1992). However, this decline in fertility due to estrogen therapy is controversial due to limited studies." 
  164. ^ a b Payne, Anita H.; Hardy, Matthew P. (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 422–431. ISBN 978-1-59745-453-7. https://books.google.com/books?id=x4ttqKIAOg0C&pg=PA422. "Estrogens are highly efficient inhibitors of the hypothalamic-hypophyseal-testicular axis (212–214). Aside from their negative feedback action at the level of the hypothalamus and pituitary, direct inhibitory effects on the testis are likely (215,216). [...] The histology of the testes [with estrogen treatment] showed disorganization of the seminiferous tubules, vacuolization and absence of lumen, and compartmentalization of spermatogenesis." 
  165. ^ a b Wakelin, Sarah H.; Maibach, Howard I.; Archer, Clive B. (1 June 2002). Systemic Drug Treatment in Dermatology: A Handbook. CRC Press. pp. 32–. ISBN 978-1-84076-013-2. オリジナルの25 July 2014時点におけるアーカイブ。. https://web.archive.org/web/20140725205131/http://books.google.com/books?id=F1ZiAgAAQBAJ&pg=PA32. "[Cyproterone acetate] inhibits spermatogenesis and produces reversible infertility (but is not a male contraceptive)." 
  166. ^ a b “The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research”. Exp. Clin. Endocrinol. 102 (1): 1–32. (1994). doi:10.1055/s-0029-1211261. PMID 8005205. "Spermatogenesis is also androgen-dependent and is inhibited by CPA, meaning that patients treated with high doses of CPA are sterile (Figure 23). All the effects of CPA are fully reversible." 
  167. ^ a b Salam, Muhammad A. (2003). Principles & Practice of Urology: A Comprehensive Text. Universal-Publishers. pp. 684–. ISBN 978-1-58112-412-5. https://books.google.com/books?id=y50kTcCCfEcC&pg=PA684. "Estrogens act primarily through negative feedback at the hypothalamic-pituitary level to reduce LH secretion and testicular androgen synthesis. [...] Interestingly, if the treatment with estrogens is discontinued after 3 yr. of uninterrupted exposure, serum testosterone may remain at castration levels for up to another 3 yr. This prolonged suppression is thought to result from a direct effect of estrogens on the Leydig cells." 
  168. ^ “Marketed Drugs Can Inhibit Cytochrome P450 27A1, a Potential New Target for Breast Cancer Adjuvant Therapy”. Molecular Pharmacology 88 (3): 428–36. (September 2015). doi:10.1124/mol.115.099598. PMC 4551053. PMID 26082378. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4551053/. 
  169. ^ “Binding of a cyano- and fluoro-containing drug bicalutamide to cytochrome P450 46A1: unusual features and spectral response”. The Journal of Biological Chemistry 288 (7): 4613–24. (February 2013). doi:10.1074/jbc.M112.438754. PMC 3576067. PMID 23288837. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3576067/. 
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  183. ^ “ICI 176,334: a novel non-steroidal, peripherally selective antiandrogen”. The Journal of Endocrinology 113 (3): R7-9. (June 1987). doi:10.1677/joe.0.113R007. PMID 3625091. 
  184. ^ “Bicalutamide in the treatment of advanced prostatic carcinoma: a phase II noncomparative multicenter trial evaluating safety, efficacy and long-term endocrine effects of monotherapy”. The Journal of Urology 154 (6): 2110–4. (December 1995). doi:10.1016/S0022-5347(01)66709-0. PMID 7500470. 
  185. ^ “Expanding the therapeutic use of androgens via selective androgen receptor modulators (SARMs)”. Drug Discovery Today 12 (5–6): 241–8. (March 2007). doi:10.1016/j.drudis.2007.01.003. PMC 2072879. PMID 17331889. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2072879/. 
  186. ^ “What implications do the tolerability profiles of antiandrogens and other commonly used prostate cancer treatments have on patient care?”. Journal of Cancer Research and Clinical Oncology 132 Suppl 1: S27-35. (August 2006). doi:10.1007/s00432-006-0134-4. PMID 16896883. 
  187. ^ a b Lemke, Thomas L.; Williams, David A. (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1372–1373. ISBN 978-1-60913-345-0. オリジナルの3 May 2016時点におけるアーカイブ。. https://web.archive.org/web/20160503223616/https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1372 
  188. ^ “Enantiomer selective glucuronidation of the non-steroidal pure anti-androgen bicalutamide by human liver and kidney: role of the human UDP-glucuronosyltransferase (UGT)1A9 enzyme”. Basic & Clinical Pharmacology & Toxicology 113 (2): 92–102. (August 2013). doi:10.1111/bcpt.12071. PMC 3815647. PMID 23527766. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/. 
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  191. ^ “Bicalutamide (Casodex) in the treatment of prostate cancer”. Expert Review of Anticancer Therapy 4 (1): 37–48. (February 2004). doi:10.1586/14737140.4.1.37. PMID 14748655. "In contrast, the incidence of diarrhea was comparable between the bicalutamide and placebo groups (6.3 vs. 6.4%, respectively) in the EPC program [71]." 
  192. ^ “Development and validation of a highly sensitive LC-MS/MS-ESI method for the determination of bicalutamide in mouse plasma: application to a pharmacokinetic study”. Biomedical Chromatography 26 (12): 1589–95. (2012). doi:10.1002/bmc.2736. PMID 22495777. 
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