Mepitiostane

Mepitiostane is used as an antiestrogen and antineoplastic agent in the treatment of breast cancer. It is also used as an AAS in the treatment of anemia of renal failure. A series of case reports have found it to be effective in the treatment of an estrogen receptor (ER)-dependent meningiomas as well.{{cite book| vauthors = Lee JH |title=Meningiomas: Diagnosis, Treatment, and Outcome|url=https://books.google.com/books?id=c_j9piinzy8C&pg=PA293|date=11 December 2008|publisher=Springer Science & Business Media|isbn=978-1-84628-784-8|pages=293–5}}{{cite journal | vauthors = Oura S, Sakurai T, Yoshimura G, Tamaki T, Umemura T, Kokawa Y, Masuo O, Naito Y | display-authors = 6 | title = Regression of a presumed meningioma with the antiestrogen agent mepitiostane. Case report | journal = Journal of Neurosurgery | volume = 93 | issue = 1 | pages = 132–135 | date = July 2000 | pmid = 10883917 | doi = 10.3171/jns.2000.93.1.0132 }}{{cite journal | vauthors = Miyai M, Takenaka K, Hayashi K, Kato M, Uematsu K, Murai H | title = [Effect of an oral anti-estrogen agent (mepitiostane) on the regression of intracranial meningiomas in the elderly] | language = ja | journal = Brain and Nerve = Shinkei Kenkyu No Shinpo | volume = 66 | issue = 8 | pages = 995–1000 | date = August 2014 | pmid = 25082321 }}

{{See also|Anabolic steroid#Adverse effects}}

Mepitiostane shows a high rate of virilizing side effects such as acne, hirsutism, and voice changes in women.{{cite journal | vauthors = 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 | display-authors = 6 | title = Therapeutic value of mepitiostane in the treatment of advanced breast cancer | journal = Cancer Treatment Reports | volume = 62 | issue = 5 | pages = 743–745 | date = May 1978 | pmid = 657160 }}

Mepitiostane is described as similar to tamoxifen as an antiestrogen,{{cite book| vauthors = Newton HB |title=Handbook of Brain Tumor Chemotherapy|url=https://books.google.com/books?id=Igz0_abuL5wC&pg=PA470|date=19 December 2005|publisher=Academic Press|isbn=978-0-08-045593-8|pages=470–}} and through its active form epitiostanol, binds directly to and antagonizes the ER.{{cite journal | vauthors = Matsuzawa A, Yamamoto T | title = Antitumor effect of two oral steroids, mepitiostane and fluoxymesterone, on a pregnancy-dependent mouse mammary tumor (TPDMT-4) | journal = Cancer Research | volume = 37 | issue = 12 | pages = 4408–4415 | date = December 1977 | pmid = 922732 }}{{cite book| vauthors = Timmerman H |title=QSAR and Drug Design: New Developments and Applications|url=https://books.google.com/books?id=I-Y4u2OQ5M0C&pg=PA145|date=20 November 1995|publisher=Elsevier|isbn=978-0-08-054500-4|pages=125, 145}}{{cite book | vauthors = Matsuzawa A | title = Hormone dependence and independence of mammary tumors in mice | series = International Review of Cytology | volume = 103 | pages = 303–40 | date = 1986 | pmid = 3017886 | doi = 10.1016/s0074-7696(08)60839-6 | isbn = 9780123645036 | url = https://books.google.com/books?id=8SuUZFjkGpwC&pg=PA319 }}{{cite journal| vauthors = Croll RP, Wang C |title=Possible roles of sex steroids in the control of reproduction in bivalve molluscs|journal=Aquaculture|volume=272|issue=1–4|year=2007|pages=76–86|issn=0044-8486|doi=10.1016/j.aquaculture.2007.06.031|bibcode=2007Aquac.272...76C }} It is also an AAS.

Mepitiostane is converted into epitiostanol in the body.

{{See also|List of androgens/anabolic steroids}}

Mepitiostane, also known as epitiostanol 17β-(1-methoxy)cyclopentyl ether,{{cite book| veditors = Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J |title=Prodrugs: Challenges and Rewards|url=https://books.google.com/books?id=qkjHxX5TgHEC&pg=PA660|date=12 March 2007|publisher=Springer Science & Business Media|isbn=978-0-387-49782-2|pages=660–}} is a synthetic androstane steroid and a derivative of DHT. It is the C17β (1-methoxy)cyclopentyl ether of epitiostanol, which itself is 2α,3α-epithio-DHT or 2α,3α-epithio-5α-androstan-17β-ol.{{cite book | vauthors = Porter CJ, Charman WN | chapter = Model Systems for Intestinal Lympahtic Transport Studies | veditors = Borchardt RT, Smith PL, Wilson G |title=Models for Assessing Drug Absorption and Metabolism| chapter-url=https://books.google.com/books?id=eS0BCAAAQBAJ&pg=PA101|date=29 June 2013|publisher=Springer Science & Business Media|isbn=978-1-4899-1863-5|pages=101–}} A related AAS is methylepitiostanol (17α-methylepitiostanol), which is an orally active variant of epitiostanol similarly to mepitiostane, though also has a risk of hepatotoxicity.{{cite journal | vauthors = Rahnema CD, Crosnoe LE, Kim ED | title = Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem | journal = Andrology | volume = 3 | issue = 2 | pages = 150–155 | date = March 2015 | pmid = 25684733 | doi = 10.1111/andr.307 | s2cid = 6999218 | doi-access = free }}

Mepitiostane is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|JAN|Japanese Accepted Name}}.

{{Reflist}}

{{Estrogens and antiestrogens}}

{{Androgens and antiandrogens}}

{{Estrogen receptor modulators}}

{{Androgen receptor modulators}}

Category:Androgen ethers

Category:Anabolic–androgenic steroids

Category:Androstanes

Category:Antiestrogens

Category:Cyclopentanes

Category:Hormonal antineoplastic drugs

Category:Prodrugs

Category:Episulfides