Mepitiostane

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Mepitiostane
Mepitiostane.png
Systematic (IUPAC) name
(2α,3α,5α,17β)-17-[(1-methoxycyclopentyl)oxy]-2,3-epithioandrostane
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
Legal status
Legal status
  • ℞ (Prescription only)
Identifiers
CAS Number 21362-69-6 YesY
ATC code none
PubChem CID 9909202
ChemSpider 8084854 N
UNII O00404969K YesY
KEGG D01602 YesY
Chemical data
Formula C25H40O2S
Molar mass 404.64 g/mol
 NYesY (what is this?)  (verify)

Mepitiostane (INN, JAN) (brand name Thioderon), also known as epitiostanol 17-methyloxycyclopentyl ether,[1] is a steroidal antiestrogen, androgen, and anabolic steroid that is used in Japan as an antineoplastic agent in the treatment of breast cancer and is also used in the treatment of anemia of renal failure.[2][3][4][5] It is the 17-methyloxycyclopentyl ether of epitiostanol, and acts as an oral prodrug to it.[1][6] Mepitiostane is described as similar to tamoxifen as an antiestrogen,[7] and through epitiostanol, binds directly to and antagonizes the estrogen receptor.[8][9][10][11] A series of case reports have found it to be effective in the treatment of an estrogen receptor-dependent meningiomas.[7][12][13][14] The drug shows a high rate of virilizing side effects such as acne, hirsutism, and voice changes in women.[15] It was patented and described in the literature in 1968.[2]

See also[edit]

References[edit]

  1. ^ a b Valentino Stella; Ronald Borchardt; Michael Hageman; Reza Oliyai; Hans Maag; Jefferson Tilley (12 March 2007). Prodrugs: Challenges and Rewards. Springer Science & Business Media. pp. 660–. ISBN 978-0-387-49782-2. 
  2. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 768. ISBN 978-1-4757-2085-3. 
  3. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 175–. ISBN 978-94-011-4439-1. 
  4. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 648–. ISBN 978-3-88763-075-1. 
  5. ^ Allan J. Erslev (1991). Erythropoietin: molecular, cellular, and clinical biology. Johns Hopkins University Press. p. 229. ISBN 978-0-8018-4221-4. 
  6. ^ Ronald T. Borchardt; Philip L. Smith; Glynn Wilson (29 June 2013). Models for Assessing Drug Absorption and Metabolism. Springer Science & Business Media. pp. 101–. ISBN 978-1-4899-1863-5. 
  7. ^ a b Herbert B. Newton (19 December 2005). Handbook of Brain Tumor Chemotherapy. Academic Press. pp. 470–. ISBN 978-0-08-045593-8. 
  8. ^ Matsuzawa A, Yamamoto T (1977). "Antitumor effect of two oral steroids, mepitiostane and fluoxymesterone, on a pregnancy-dependent mouse mammary tumor (TPDMT-4)". Cancer Res. 37 (12): 4408–15. PMID 922732. 
  9. ^ H. Timmerman (20 November 1995). QSAR and Drug Design: New Developments and Applications. Elsevier. pp. 125, 145. ISBN 978-0-08-054500-4. 
  10. ^ INTERNATIONAL REVIEW OF CYTOLOGY. Academic Press. 27 June 1986. pp. 319–. ISBN 978-0-08-058640-3. 
  11. ^ Croll, Roger P.; Wang, Chunde (2007). "Possible roles of sex steroids in the control of reproduction in bivalve molluscs". Aquaculture. 272 (1-4): 76–86. doi:10.1016/j.aquaculture.2007.06.031. ISSN 0044-8486. 
  12. ^ Joung H. Lee (11 December 2008). Meningiomas: Diagnosis, Treatment, and Outcome. Springer Science & Business Media. pp. 293–5. ISBN 978-1-84628-784-8. 
  13. ^ Oura, Shoji; Sakurai, Takeo; Yoshimura, Goro; Tamaki, Takeshi; Umemura, Teiji; Kokawa, Yozo; Masuo, Osamu; Naito, Yasuaki (2000). "Regression of a presumed meningioma with the antiestrogen agent mepitiostane". Journal of Neurosurgery. 93 (1): 132–135. doi:10.3171/jns.2000.93.1.0132. ISSN 0022-3085. 
  14. ^ Miyai M, Takenaka K, Hayashi K, Kato M, Uematsu K, Murai H (2014). "[Effect of an oral anti-estrogen agent (mepitiostane) on the regression of intracranial meningiomas in the elderly]". Brain Nerve (in Japanese). 66 (8): 995–1000. PMID 25082321. 
  15. ^ Inoue K, Okazaki K, Morimoto T, Hayashi M, Uyama S, Sonoo H, Koshiba Y, Takihara T, Nomura Y, Yamagata J, Kondo H, Kanda K, Takenaka K (1978). "Therapeutic value of mepitiostane in the treatment of advanced breast cancer". Cancer Treat Rep. 62 (5): 743–5. PMID 657160.