Fluoxymesterone

Fluoxymesterone
Clinical data
Trade names	Halotestin, Ora-Testryl, Ultandren, others
Other names	Fluoxymestrone; Androfluorene; NSC-12165; 9α-Fluoro-11β-hydroxy-17α-methyltestosterone; 9α-Fluoro-17α-methylandrost-4-en-11β,17β-diol-3-one
AHFS/Drugs.com	Monograph
MedlinePlus	a682690
Pregnancy; category	X;
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid
ATC code	G03BA01 (WHO) ;
Legal status
Legal status	BR: Class C5 (Anabolic steroids); CA: Schedule IV; US: Schedule III;
Pharmacokinetic data
Bioavailability	Oral: 80%
Metabolism	Liver (6β-hydroxylation, 5α- and 5β-reduction, 3α- and 3β-keto-oxidation, 11β-hydroxy-oxidation)
Metabolites	• 5α-Dihydrofluoxymesterone; • 11-Oxofluoxymesterone
Elimination half-life	9.2 hours
Excretion	Urine (<5% unchanged)
Identifiers
	IUPAC name (8S,9R,10S,11S,13S,14S,17S)-9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one;
CAS Number	76-43-7 ;
PubChem CID	6446;
IUPHAR/BPS	2861;
DrugBank	DB01185 ;
ChemSpider	6205 ;
UNII	9JU12S4YFY;
KEGG	D00327 ;
ChEBI	CHEBI:5120 ;
ChEMBL	ChEMBL1445 ;
CompTox Dashboard (EPA)	DTXSID8033512 ;
ECHA InfoCard	100.000.875
Chemical and physical data
Formula	C20H29FO3
Molar mass	336.447 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C3/[C@]([C@@]2(F)[C@@H](O)C[C@]1([C@@H](CC[C@@]1(O)C)[C@@H]2CC3)C)(C)CC4;
	InChI 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 ; Key:YLRFCQOZQXIBAB-RBZZARIASA-N ;
	(verify)

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia.^[1] It is taken by mouth.^[1]

Side effects of fluoxymesterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.^[1] It can also cause liver damage and cardiovascular side effects like high blood pressure.^[1]^[7]^[8] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).^[1]^[9] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization.^[1]^[10]

Fluoxymesterone was first described in 1956 and was introduced for medical use in 1957.^[1]^[11] In addition to its medical use, fluoxymesterone is used to improve physique and performance.^[1] The drug is a controlled substance in many countries and so non-medical use is generally illicit.^[1]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 500–508. ISBN 978-0-9828280-1-4.
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ ^a ^b Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1360–. ISBN 978-1-60913-345-0.
^ ^a ^b ^c ^d 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.
^ Cite error: The named reference Roberts2009 was invoked but never defined (see the help page).
^ Lemke TL, Williams DA (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1279–. ISBN 978-0-7817-6879-5.
^ Cite error: The named reference pmid22273746 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid26074745 was invoked but never defined (see the help page).
^ Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
^ Kochakian CD (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 370, 374, 401, 454, 504–506. ISBN 978-3-642-66353-6.
^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).

[Llewellyn2011-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 500–508. ISBN 978-0-9828280-1-4.

[2] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[LemkeWilliams2012-3] Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1360–. ISBN 978-1-60913-345-0.

[pmid2214783-4] 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.

[Roberts2009-5] Cite error: The named reference Roberts2009 was invoked but never defined (see the help page).

[LemkeWilliams2008-6] Lemke TL, Williams DA (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1279–. ISBN 978-0-7817-6879-5.

[pmid22273746-7] Cite error: The named reference pmid22273746 was invoked but never defined (see the help page).

[pmid26074745-8] Cite error: The named reference pmid26074745 was invoked but never defined (see the help page).

[pmid18500378-9] Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.

[Kochakian2012-10] Kochakian CD (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 370, 374, 401, 454, 504–506. ISBN 978-3-642-66353-6.

[Publishing2013-11] Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).

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