Atamestane

Atamestane

Clinical data
Other names	SH-489; Metandroden; 1-Methylandrosta-1,4-diene-3,17-dione
Routes of administration	By mouth
ATC code	None
Legal status
Legal status	UK: Class C
Identifiers
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
CAS Number	96301-34-7 Y
PubChem CID	57050
ChemSpider	51438 Y
UNII	62GA3K28B6
ChEMBL	ChEMBL2105987 Y
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C20H26O2
Molar mass	298.426 g·mol−1
3D model (JSmol)	Interactive image
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
InChI InChI=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 Y Key:PEPMWUSGRKINHX-TXTPUJOMSA-N Y

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. It blocks the production of estrogen in the body. The drug is selective, competitive, and irreversible in its inhibition of aromatase.

Synthesis

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). 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.

External links

• Atamestane entry in the public domain NCI Dictionary of Cancer Terms

 This article incorporates public domain material from