French
DeutschMepitiostane
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| Clinical data | |
|---|---|
| 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 |
| ATC code |
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| Legal status | |
| Legal status |
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| Identifiers | |
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| CAS Number | |
| PubChem CID | |
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| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C25H40O2S |
| Molar mass | 404.65 g·mol−1 |
| 3D model (JSmol) | |
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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
[edit]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
[edit]Mepitiostane shows a high rate of virilizing side effects such as acne, hirsutism, and voice changes in women.[12]
Pharmacology
[edit]Pharmacodynamics
[edit]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
[edit]Mepitiostane is converted into epitiostanol in the body.[6][7]
Chemistry
[edit]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
[edit]Generic names
[edit]Mepitiostane is the generic name of the drug and its INN and JAN.[1][2][3]
References
[edit]- ^ a b c d e f Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 768. ISBN 978-1-4757-2085-3.
- ^ a b c d Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 648–. ISBN 978-3-88763-075-1.
- ^ a b c d e Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 175–. ISBN 978-94-011-4439-1.
- ^ "Mepitiostane".
- ^ a b c Erslev AJ (1991). Erythropoietin: molecular, cellular, and clinical biology. Johns Hopkins University Press. p. 229. ISBN 978-0-8018-4221-4.
- ^ a b c d Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J, eds. (12 March 2007). Prodrugs: Challenges and Rewards. Springer Science & Business Media. pp. 660–. ISBN 978-0-387-49782-2.
- ^ a b Borchardt RT, Smith PL, Wilson G (29 June 2013). Models for Assessing Drug Absorption and Metabolism. Springer Science & Business Media. pp. 101–. ISBN 978-1-4899-1863-5.
- ^ a b Newton HB (19 December 2005). Handbook of Brain Tumor Chemotherapy. Academic Press. pp. 470–. ISBN 978-0-08-045593-8.
- ^ Lee JH (11 December 2008). Meningiomas: Diagnosis, Treatment, and Outcome. Springer Science & Business Media. pp. 293–5. ISBN 978-1-84628-784-8.
- ^ Oura S, Sakurai T, Yoshimura G, Tamaki T, Umemura T, Kokawa Y, et al. (July 2000). "Regression of a presumed meningioma with the antiestrogen agent mepitiostane. Case report". Journal of Neurosurgery. 93 (1): 132–135. doi:10.3171/jns.2000.93.1.0132. PMID 10883917.
- ^ Miyai M, Takenaka K, Hayashi K, Kato M, Uematsu K, Murai H (August 2014). "[Effect of an oral anti-estrogen agent (mepitiostane) on the regression of intracranial meningiomas in the elderly]". Brain and Nerve = Shinkei Kenkyu No Shinpo (in Japanese). 66 (8): 995–1000. PMID 25082321.
- ^ Inoue K, Okazaki K, Morimoto T, Hayashi M, Uyama S, Sonoo H, et al. (May 1978). "Therapeutic value of mepitiostane in the treatment of advanced breast cancer". Cancer Treatment Reports. 62 (5): 743–745. PMID 657160.
- ^ Matsuzawa A, Yamamoto T (December 1977). "Antitumor effect of two oral steroids, mepitiostane and fluoxymesterone, on a pregnancy-dependent mouse mammary tumor (TPDMT-4)". Cancer Research. 37 (12): 4408–4415. PMID 922732.
- ^ Timmerman H (20 November 1995). QSAR and Drug Design: New Developments and Applications. Elsevier. pp. 125, 145. ISBN 978-0-08-054500-4.
- ^ Matsuzawa A (1986). Hormone dependence and independence of mammary tumors in mice. International Review of Cytology. Vol. 103. pp. 303–40. doi:10.1016/s0074-7696(08)60839-6. ISBN 9780123645036. PMID 3017886.
- ^ Croll RP, Wang C (2007). "Possible roles of sex steroids in the control of reproduction in bivalve molluscs". Aquaculture. 272 (1–4): 76–86. Bibcode:2007Aquac.272...76C. doi:10.1016/j.aquaculture.2007.06.031. ISSN 0044-8486.
- ^ Porter CJ, Charman WN (29 June 2013). "Model Systems for Intestinal Lympahtic Transport Studies". In Borchardt RT, Smith PL, Wilson G (eds.). Models for Assessing Drug Absorption and Metabolism. Springer Science & Business Media. pp. 101–. ISBN 978-1-4899-1863-5.
- ^ Rahnema CD, Crosnoe LE, Kim ED (March 2015). "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology. 3 (2): 150–155. doi:10.1111/andr.307. PMID 25684733. S2CID 6999218.