Oxofluoxymesterone

Oxofluoxymesterone
Clinical data
Other names	U-6596; Ketofluoxymesterone; 11-Oxofluoxymesterone; 11-Ketofluoxymesterone; 9α-Fluoro-11-oxo-17α-methyltestosterone; 9α-Fluoro-17α-methylandrost-4-en-17β-ol-3,11-dione
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid
Identifiers
	IUPAC name (8S,9R,10S,13S,14S,17S)-9-fluoro-17-hydroxy-10,13,17-trimethyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione;
CAS Number	465-69-0;
PubChem CID	10065;
ChemSpider	9669;
UNII	0083BRI2A7;
KEGG	C14621;
ChEBI	CHEBI:34510;
ChEMBL	ChEMBL406406;
CompTox Dashboard (EPA)	DTXSID90196860 ;
Chemical and physical data
Formula	C20H27FO3
Molar mass	334.431 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@]2(C(=O)C[C@]4([C@H]3CC[C@]4(C)O)C)F;
	InChI InChI=1S/C20H27FO3/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/h10,14-15,24H,4-9,11H2,1-3H3/t14-,15-,17-,18-,19-,20-/m0/s1; Key:YUMWOIMGKYOLOA-MWTXUKJESA-N;

Oxofluoxymesterone (developmental code name U-6596), or ketofluoxymesterone, is an androgen and anabolic steroid (AAS) which was never marketed.^[1]^[2]^[3] It was assessed in the treatment of breast cancer in women in the 1970s and showed effectiveness similar to that of other AAS.^[1]^[2]^[4] The drug is the 11-dehydrogenated analogue and a metabolite of fluoxymesterone.^[1]^[2]^[3]^[5]

References edit

^ ^a ^b ^c Gordan, G. S. (1976). "Cancer in Man". Anabolic-Androgenic Steroids. pp. 499–513. doi:10.1007/978-3-642-66353-6_16. ISBN 978-3-642-66355-0.
^ ^a ^b ^c Charles D. Kochakian (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 504–. ISBN 978-3-642-66353-6.
^ ^a ^b Kammerer RC, Merdink JL, Jagels M, Catlin DH, Hui KK (1990). "Testing for fluoxymesterone (Halotestin) administration to man: identification of urinary metabolites by gas chromatography-mass spectrometry". J. Steroid Biochem. 36 (6): 659–66. doi:10.1016/0022-4731(90)90185-u. PMID 2214783.
^ Dao, Thomas L. (1975). "Pharmacology and Clinical Utility of Hormones in Hormone Related Neoplasms". In Alan C. Sartorelli; David G. Johns (eds.). Antineoplastic and Immunosuppressive Agents. pp. 170–192. doi:10.1007/978-3-642-65806-8_11. ISBN 978-3-642-65806-8.
^ Fürstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A (2012). "The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation". Toxicol. Sci. 126 (2): 353–61. doi:10.1093/toxsci/kfs022. PMID 22273746.

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Clinical data

Other names	U-6596; Ketofluoxymesterone; 11-Oxofluoxymesterone; 11-Ketofluoxymesterone; 9α-Fluoro-11-oxo-17α-methyltestosterone; 9α-Fluoro-17α-methylandrost-4-en-17β-ol-3,11-dione
Routes of administration	By mouth
Drug class	Androgen; Anabolic steroid
Identifiers
IUPAC name (8S,9R,10S,13S,14S,17S)-9-fluoro-17-hydroxy-10,13,17-trimethyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
CAS Number	465-69-0
PubChem CID	10065
ChemSpider	9669
UNII	0083BRI2A7
KEGG	C14621
ChEBI	CHEBI:34510
ChEMBL	ChEMBL406406
CompTox Dashboard (EPA)	DTXSID90196860
Chemical and physical data
Formula	C₂₀H₂₇FO₃
Molar mass	334.431 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@]2(C(=O)C[C@]4([C@H]3CC[C@]4(C)O)C)F
InChI InChI=1S/C20H27FO3/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/h10,14-15,24H,4-9,11H2,1-3H3/t14-,15-,17-,18-,19-,20-/m0/s1 Key:YUMWOIMGKYOLOA-MWTXUKJESA-N