Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00284)
Name
Fluoxymesterone
Synonyms    Click to Show/Hide the Synonyms of This API
fluoxymesterone; 76-43-7; Fluoxymestrone; Fluoximesterone; Halotestin; Androfluorene; Androfluorone; Fluotestin; Androsterolo; Fluosterone; Flusteron; Flutestos; Oralsterone; Oratestin; Testoral; Ultandren; Ultandrene; Fluoximesteronum; Android-f; Neo-Ormonal; Ora Testryl; Ora-Testryl; Fluoximesterona; Fluossimesterone [DCIT]; Fluoxymesteronum; Anadroid-F; Fluoxymesteronum [INN-Latin]; Fluoximesterona [INN-Spanish]; NSC-12165; Fluoxymesteron; 9alpha-Fluoro-11beta-hydroxy-17-methyltestosterone; UNII-9JU12S4YFY; U 6040; 9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one; NSC 10704; Testosterone, 9-fluoro-11beta-hydroxy-17-methyl-; 9JU12S4YFY; CHEBI:5120; (11beta,17beta)-9-fluoro-11,17-dihydroxy-17-methylandrost-4-en-3-one; 17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesterone; NSC-10704; component of Halodrin; Fluossimesterone; 11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one; DSSTox_CID_13512; DSSTox_RID_79080; DSSTox_GSID_33512; 9.alpha.-Fluoro-11.beta.-hydroxy-17-methyltestosterone; Androxy; Fluoxymesterone, 97.0-102.0%; Androst-4-en-3-one, 9-fluoro-11,17-dihydroxy-17-methyl-, (11beta,17beta)-; 9alpha-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one; 9.alpha.-Fluoro-11.beta.,17.beta.-dihydroxy-17.alpha.-methyl-4-androstene-3-one; CAS-76-43-7; Halotestin (TN); CCRIS 9036; HSDB 3333; EINECS 200-961-8; Testosterone, 9-fluoro-11.beta.-hydroxy-17-methyl-; BRN 2008796; 9-alpha-Fluoro-11-beta-hydroxy-17-methyltestosterone; 17-alpha-Methyl-9-alpha-fluoro-11-beta-hydroxytesterone; AI3-52940; 9-Fluoro-11-beta,17-beta-dihydroxy-17-methylandrost-4-en-3-one; 9alpha-Fluoro-17alpha-methyl-11beta,17-dihydroxy-4-androsten-3-one; NCGC00182970-01; 11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androsten-3-one; 9-alpha-Fluoro-17-alpha-methyl-11-beta,17-dihydroxy-4-androsten-3-one; 9alpha-Fluoro-11beta,17beta-dihydroxy-17alpha-methyl-4-androstene-3-one; Fluoxymesterone ciii; Androxy (TN); 11-beta,17-beta-Dihydroxy-9-alpha-fluoro-17-alpha-methyl-4-androster-3-one; 9-alpha-Fluoro-11-beta,17-beta-dihydroxy-17-alpha-methyl-4-androstene-3-one; Fluoxymesterone [USP:INN:BAN:JAN]; PubChem5785; Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl-; Fluoro-9-alpha dihydroxy-11-beta,17-beta methyl-17-alpha androstene-4 one-3; SCHEMBL5096; CHEMBL1445; 4-08-00-02057 (Beilstein Handbook Reference); MLS001055414; GTPL2861; DTXSID8033512; BDBM18189; Fluoxymesterone (JAN/USP/INN); HMS2272B06; BCP10776; NSC10704; NSC12165; ZINC3875484; Tox21_113158; Tox21_200854; 9-fluoro-11beta,17beta-dihydroxy-17alpha-methylandrost-4-en-3-one; LMST02020025; AKOS015895109; DB01185; Fluoxymesterone, solid (photosensitive); NCGC00091037-01; NCGC00091037-02; NCGC00258408-01; AC-29744; SMR000686158; Fluoxymesterone 1.0 mg/ml in Acetonitrile; D00327; 92481-EP2295416A2; 92481-EP2295426A1; 92481-EP2295427A1; 92481-EP2298748A2; 92481-EP2305642A2; 010F480; A838701; Q410663; W-104363; Androst-4-en-3-one, 9-fluoro-11beta,17beta-dihydroxy-17-methyl- (VAN) (8CI)
Clinical Status
Approved
Disease Indication Breast cancer ICD-11: 2C60 [1]
PubChem CID
6446
Formula
C20H29FO3
Canonical SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@]2([C@H](C[C@]4([C@H]3CC[C@]4(C)O)C)O)F
InChI
1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1
InChIKey
YLRFCQOZQXIBAB-RBZZARIASA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6446"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 336.4 Topological Polar Surface Area 57.5
XlogP 2.4 Complexity 630
Heavy Atom Count 24 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Fluoxymesterone 10 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Anhydrous lactose; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Magnesium stearate; Croscarmellose sodium; Aluminum oxide; Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company Upsher-Smith Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
References
1 FDA label for approved fluoxymesterone from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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