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{{Short description|Chemical compound}} |
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{{drugbox |
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{{Drugbox |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| Watchedfields = changed |
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| verifiedrevid = 437193284 |
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| UNII = PUB9T8T355 |
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| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'')-4-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1''H''-cyclopentaphenanthrene-3,17-dione |
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| verifiedrevid = 407820334 |
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| image = Formestane.svg |
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| width = 225px |
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|IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'')-4-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1''H''-cyclopentaphenanthrene-3,17-dione |
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|synonyms=<small>4-hydroxyandrost-4-ene-3,17-dione</small> |
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<!--Clinical data--> |
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| image= Formestane.svg |
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| tradename = Lentaron, others |
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| Drugs.com = {{drugs.com|international|formestane}} |
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| pregnancy_category = |
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| legal_status = |
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| routes_of_administration = ] |
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| class = ]; ] |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 566-48-3 |
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| ATC_prefix = L02 |
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| ATC_suffix = BG02 |
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| PubChem = 11273 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10799 |
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| ChemSpiderID = 10799 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1 |
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| UNII = PUB9T8T355 |
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| InChIKey = OSVMTWJCGUFAOD-KZQROQTABI |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| smiles = O=C4C(/O)=C3/CC2(CC1(C(=O)CC12)C)3(C)CC4 |
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| KEGG = D07260 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 75172 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 132530 |
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| ChEMBL = 132530 |
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| synonyms = 4-Hydroxyandrost-4-ene-3,17-dione |
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<!--Chemical data--> |
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| C=19 | H=26 | O=3 |
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| SMILES = O=C4C(/O)=C3/CC2(CC1(C(=O)CC12)C)3(C)CC4 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1 |
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| StdInChI = 1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = OSVMTWJCGUFAOD-KZQROQTASA-N |
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| StdInChIKey = OSVMTWJCGUFAOD-KZQROQTASA-N |
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| CAS_number=566-48-3 |
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| ATC_prefix=L02 |
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| ATC_suffix=BG02 |
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| ATC_supplemental= |
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| PubChem=11273 |
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| DrugBank= |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07260 |
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| C = 19 | H = 26 | O = 3 |
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| molecular_weight = 302.408 g/mol |
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| bioavailability= |
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| metabolism = |
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| elimination_half-life= |
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| excretion = |
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| pregnancy_category = |
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| legal_status = |
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| routes_of_administration= |
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}} |
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}} |
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'''Formestane''' belongs to a class of drugs known as 2 ]. It is used in the treatment of estrogen-receptor positive breast cancer in post-menopausal women. It is available as an intramuscular depot injection (Lentaron). |
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'''Formestane''', formerly sold under the brand name '''Lentaron''' among others, is a ]al, ] ] which is used in the treatment of ]-positive ] in ] women.<ref name="pmid7873457">{{cite journal |vauthors=Pérez Carrión R, Alberola Candel V, Calabresi F |title=Comparison of the selective aromatase inhibitor formestane with tamoxifen as first-line hormonal therapy in postmenopausal women with advanced breast cancer |journal=Ann. Oncol. |volume=5 |pages=S19–24 |year=1994 |issue=Suppl 7 |pmid=7873457 |display-authors=etal}}</ref> The drug is not active orally, and was available only as an intramuscular depot injection. Formestane was not approved by the United States FDA and the injectable form that was used in Europe in the past has been withdrawn from the market.<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/formestane#section=Top|title = Formestane}}</ref> Formestane is an ] of ]. |
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Formestane is often used to suppress ] production from ] or ]. It also acts as a prohormone to ], an active steroid which displays weak ] activity in addition to acting as a mild aromatase inhibitor. |
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Formestane is often used to suppress the production of estrogens from ]s or ]s. It also acts as a prohormone to ], an active steroid which displays weak ] activity in addition to acting as a weak aromatase inhibitor. |
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Formestane has poor oral bioavailability and as such is no longer popular as many orally active aromatase inhibitors have been identified. |
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{{Pharmacodynamics of aromatase inhibitors}} |
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It is selective.<ref name="pmid7873457">{{cite journal |author=Pérez Carrión R, Alberola Candel V, Calabresi F, ''et al.'' |title=Comparison of the selective aromatase inhibitor formestane with tamoxifen as first-line hormonal therapy in postmenopausal women with advanced breast cancer |journal=Ann. Oncol. |volume=5 Suppl 7 |issue= |pages=S19–24 |year=1994 |pmid=7873457 |doi= |url=}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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{{Sex hormones}} |
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{{Estrogens and antiestrogens}} |
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] |
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{{Androgen receptor modulators}} |
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] |
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{{antineoplastic-drug-stub}} |
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{{antineoplastic-drug-stub}} |
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{{steroid-stub}} |