Atamestane

{{Drugbox

| IUPAC_name = (8R,9S,10S,13S,14S)-1,10,13-Trimethyl-7,8,9,11,12, 14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione

| image = Atamestane.svg

| width = 250

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| legal_UK = Class C

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| routes_of_administration = By mouth{{cite journal | vauthors = el Etreby MF, Nishino Y, Habenicht UF, Henderson D | title = Atamestane, a new aromatase inhibitor for the management of benign prostatic hyperplasia | journal = Journal of Andrology | volume = 12 | issue = 6 | pages = 403–414 | date = 1991-11-12 | pmid = 1722797 | doi = 10.1002/j.1939-4640.1991.tb00283.x }}

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| CAS_number = 96301-34-7

| ATC_prefix = None

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| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C20H26O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10-11,15-17H,4-9H2,1-3H3/t15-,16-,17-,19-,20-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = PEPMWUSGRKINHX-TXTPUJOMSA-N

| PubChem = 57050

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| ChEMBL = 2105987

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| ChemSpiderID = 51438

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| UNII = 62GA3K28B6

| chemical_formula =

| C=20 | H=26 | O=2

| smiles = O=C\1/C=C(/C)[C@]4(C(=C/1)/CC[C@@H]3[C@@H]4CC[C@@]2(C(=O)CC[C@H]23)C)C

| synonyms = SH-489; Metandroden; 1-Methylandrosta-1,4-diene-3,17-dione

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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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA794|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=794–}} It blocks the production of estrogen in the body. The drug is selective, competitive, and irreversible in its inhibition of aromatase.{{cite journal | vauthors = el Etreby MF | s2cid = 53256276 | title = Atamestane: an aromatase inhibitor for the treatment of benign prostatic hyperplasia. A short review | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 44 | issue = 4–6 | pages = 565–72 | date = March 1993 | pmid = 7682838 | doi = 10.1016/0960-0760(93)90260-4 }}{{Additional citation needed|date=December 2016}}

Synthesis

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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).{{cite patent |country=US |number=4871482 |inventor = Klaus N, Hanfried A |title=Process for the preparation of 1-methylandrosta-1,4-diene-3,17,dione, and the novel intermediates for this process |status=patent |gdate=1989-10-03 |fdate=1988-05-06 |assign1= Schering AG }} 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.{{cite journal |doi=10.1016/S0040-4020(01)89518-1 |title=Regioselective synthesis of ring a polymethylated steroids in the androstane series |date=1989 | vauthors = Künzer H, Sauer G, Wiechert R |journal=Tetrahedron |volume=45 |issue=20 |pages=6409–6426 }}

References

External links

[http://www.cancer.gov/dictionary?CdrID=45002 Atamestane] entry in the public domain NCI Dictionary of Cancer Terms

Category:Anabolic–androgenic steroids

Category:Androstanes

Category:Aromatase inhibitors

Category:Enantiopure drugs