Chemistry:Atamestane
Atamestane (developmental code name SH-489), also known as metandroden, as well as 1-methylandrosta-1,4-diene-3,17-dione, is a steroidal aromatase inhibitor that was studied in the treatment of cancer.[1] It blocks the production of estrogen in the body. The drug is selective, competitive, and irreversible in its inhibition of aromatase.[2][additional citation(s) needed]
Synthesis
- upright=2
Reaction of the known compound, androstadienedione, (1) with Gilman reagent followed by acetylation with acetic anhydride gives the enol acetate (2). Bromination with 1,3-dibromo-5,5-dimethylhydantoin gives an intermediate (3) which on treatment with magnesium oxide yields atamestane (4).[3] Alternatively the steroid (5) can be oxidized with benzeneselenol, or the natural product, boldenone (6) can be oxidized with a mixture of chromium trioxide and sulfuric acid.[4]
References
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 794–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA794.
- ↑ "Atamestane: an aromatase inhibitor for the treatment of benign prostatic hyperplasia. A short review". The Journal of Steroid Biochemistry and Molecular Biology 44 (4–6): 565–72. March 1993. doi:10.1016/0960-0760(93)90260-4. PMID 7682838.
- ↑ Klaus N, Hanfried A, "Process for the preparation of 1-methylandrosta-1,4-diene-3,17,dione, and the novel intermediates for this process", US patent 4871482, issued 1989-10-03, assigned to Schering AG
- ↑ "Regioselective synthesis of ring a polymethylated steroids in the androstane series". Tetrahedron 45 (20): 6409–6426. 1989. doi:10.1016/S0040-4020(01)89518-1.
External links
- Atamestane entry in the public domain NCI Dictionary of Cancer Terms
This article incorporates public domain material from the U.S. National Cancer Institute document "Dictionary of Cancer Terms".
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