Chemistry:Mepitiostane
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| Trade names | Thioderon |
| Other names | 10364-S; Epitiostanol 17β-(1-methoxy)cyclopentyl ether; 17β-[(1-Methoxycyclopentyl)oxy]-2α,3α-epithio-5α-androstane |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | By mouth |
| Drug class | Androgen; Anabolic steroid; Androgen ether; Antiestrogen |
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| Legal status |
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| Chemical and physical data | |
| Formula | C25H40O2S |
| Molar mass | 404.65 g·mol−1 |
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Mepitiostane, sold under the brand name Thioderon, is an orally active antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which is marketed in Japan as an antineoplastic agent for the treatment of breast cancer.[1][2][3][4][5] It is a prodrug of epitiostanol.[6][7] The drug was patented and described in 1968.[1]
Medical uses
Mepitiostane is used as an antiestrogen and antineoplastic agent in the treatment of breast cancer.[1][2][3][5] It is also used as an AAS in the treatment of anemia of renal failure.[5] A series of case reports have found it to be effective in the treatment of an estrogen receptor (ER)-dependent meningiomas as well.[8][9][10][11]
Side effects
Mepitiostane shows a high rate of virilizing side effects such as acne, hirsutism, and voice changes in women.[12]
Pharmacology
Pharmacodynamics
Mepitiostane is described as similar to tamoxifen as an antiestrogen,[8] and through its active form epitiostanol, binds directly to and antagonizes the ER.[13][14][15][16] It is also an AAS.[1][3]
Pharmacokinetics
Mepitiostane is converted into epitiostanol in the body.[6][7]
Chemistry
Mepitiostane, also known as epitiostanol 17β-(1-methoxy)cyclopentyl ether,[6] is a synthetic androstane steroid and a derivative of DHT.[1][2][3] 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.[6][17] 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.[18]
Society and culture
Generic names
Mepitiostane is the generic name of the drug and its INN and JAN.[1][2][3]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 768. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA768.
- ↑ 2.0 2.1 2.2 2.3 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 648–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA648.
- ↑ 3.0 3.1 3.2 3.3 3.4 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 175–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA175.
- ↑ "Mepitiostane". https://www.drugs.com/international/mepitiostane.html.
- ↑ 5.0 5.1 5.2 Erythropoietin: molecular, cellular, and clinical biology. Johns Hopkins University Press. 1991. p. 229. ISBN 978-0-8018-4221-4. https://books.google.com/books?id=CFtsAAAAMAAJ.
- ↑ 6.0 6.1 6.2 6.3 Prodrugs: Challenges and Rewards. Springer Science & Business Media. 12 March 2007. pp. 660–. ISBN 978-0-387-49782-2. https://books.google.com/books?id=qkjHxX5TgHEC&pg=PA660.
- ↑ 7.0 7.1 Models for Assessing Drug Absorption and Metabolism. Springer Science & Business Media. 29 June 2013. pp. 101–. ISBN 978-1-4899-1863-5. https://books.google.com/books?id=eS0BCAAAQBAJ&pg=PA101.
- ↑ 8.0 8.1 Handbook of Brain Tumor Chemotherapy. Academic Press. 19 December 2005. pp. 470–. ISBN 978-0-08-045593-8. https://books.google.com/books?id=Igz0_abuL5wC&pg=PA470.
- ↑ Meningiomas: Diagnosis, Treatment, and Outcome. Springer Science & Business Media. 11 December 2008. pp. 293–5. ISBN 978-1-84628-784-8. https://books.google.com/books?id=c_j9piinzy8C&pg=PA293.
- ↑ "Regression of a presumed meningioma with the antiestrogen agent mepitiostane. Case report". Journal of Neurosurgery 93 (1): 132–135. July 2000. doi:10.3171/jns.2000.93.1.0132. PMID 10883917.
- ↑ "[Effect of an oral anti-estrogen agent (mepitiostane) on the regression of intracranial meningiomas in the elderly]" (in ja). Brain and Nerve = Shinkei Kenkyu No Shinpo 66 (8): 995–1000. August 2014. PMID 25082321.
- ↑ "Therapeutic value of mepitiostane in the treatment of advanced breast cancer". Cancer Treatment Reports 62 (5): 743–745. May 1978. PMID 657160.
- ↑ "Antitumor effect of two oral steroids, mepitiostane and fluoxymesterone, on a pregnancy-dependent mouse mammary tumor (TPDMT-4)". Cancer Research 37 (12): 4408–4415. December 1977. PMID 922732.
- ↑ QSAR and Drug Design: New Developments and Applications. Elsevier. 20 November 1995. pp. 125, 145. ISBN 978-0-08-054500-4. https://books.google.com/books?id=I-Y4u2OQ5M0C&pg=PA145.
- ↑ "Hormone dependence and independence of mammary tumors in mice". International Review of Cytology 103: 303–40. 1986. doi:10.1016/s0074-7696(08)60839-6. ISBN 9780123645036. PMID 3017886. https://books.google.com/books?id=8SuUZFjkGpwC&pg=PA319.
- ↑ "Possible roles of sex steroids in the control of reproduction in bivalve molluscs". Aquaculture 272 (1–4): 76–86. 2007. doi:10.1016/j.aquaculture.2007.06.031. ISSN 0044-8486.
- ↑ "Model Systems for Intestinal Lympahtic Transport Studies". Models for Assessing Drug Absorption and Metabolism. Springer Science & Business Media. 29 June 2013. pp. 101–. ISBN 978-1-4899-1863-5. https://books.google.com/books?id=eS0BCAAAQBAJ&pg=PA101.
- ↑ "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology 3 (2): 150–155. March 2015. doi:10.1111/andr.307. PMID 25684733.
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