Structure via PubChem · Public domain (PubChem)
atamestane
Sign in to saveAtamestane (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.
Chemical data
- Formula
- C20H26O2
- Molecular weight
- 298.4 g/mol
- 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
- SMILES
- CC1=CC(=O)C=C2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CCC4=O)C)C
- InChIKey
- PEPMWUSGRKINHX-TXTPUJOMSA-N
- XLogP
- 2.9
- Polar surface area
- 34.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- breast neoplasm, breast cancer
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 298.193
Show 5 more facts
- chemical formula
- C₂₀H₂₆O₂
- canonical SMILES
- CC1=CC(=O)C=C2C1(C3CCC4(C(C3CC2)CCC4=O)C)C
- isomeric SMILES
- CC1=CC(=O)C=C2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CCC4=O)C)C
- subject has role
- aromatase inhibitors
- Commons category
- Atamestane
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- References
- External links
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== Dof: 600px 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 PC10380080 (6) can be oxidized with a mixture of chromium trioxide and sulfuric acid.
Excerpted from Wikipedia’s “atamestane” article, available under the CC BY-SA 4.0 licence.