View source for Chemistry:Atamestane

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458476237
| IUPAC_name = (8''R'',9''S'',10''S'',13''S'',14''S'')-1,10,13-Trimethyl-7,8,9,11,12, 14,15,16-octahydro-6''H''-cyclopenta[a]phenanthrene-3,17-dione
| image = Atamestane.svg
| width = 250

<!--Clinical data-->
| tradename =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =  
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = Class C
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =  
| routes_of_administration =  

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
| metabolism =  
| elimination_half-life =  
| excretion =  

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 96301-34-7
| ATC_prefix = None
| ATC_suffix =  
| ATC_supplemental =  
| 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
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =  
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2105987
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 51438
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 62GA3K28B6

<!--Chemical data-->
| 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
}}

'''Atamestane''' (developmental code name '''SH-489'''), also known as '''metandroden''', as well as '''1-methylandrosta-1,4-diene-3,17-dione''', is a [[Biology:Steroid|steroid]]al [[Chemistry:Aromatase inhibitor|aromatase inhibitor]] that was studied in the treatment of [[Medicine:Cancer|cancer]].<ref name="Elks2014">{{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–}}</ref> It blocks the production of [[Biology:Estrogen|estrogen]] in the body. The drug is selective, competitive, and irreversible in its [[Biology:Enzyme inhibitor|inhibition]] of [[Biology:Aromatase|aromatase]].<ref name="pmid7682838">{{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 }}</ref>{{Additional citation needed|date=December 2016}}

== See also ==
* [[Chemistry:Boldione|Boldione]] (androsta-1,4-diene-3,17-dione)

== References ==
{{Reflist|2}}

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

{{NCI-cancer-dict}}

{{Androgen receptor modulators}}

[[Category:Androstanes]]
[[Category:Aromatase inhibitors]]
[[Category:Enantiopure drugs]]


{{Sourceattribution|Atamestane}}