Fluoxymesterone

Fluoxymesterone
Clinical data
Trade namesHalotestin, Ora-Testryl, Ultandren, others
Other namesFluoxymestrone; Androfluorene; NSC-12165; 9α-Fluoro-11β-hydroxy-17α-methyltestosterone; 9α-Fluoro-17α-methylandrost-4-en-11β,17β-diol-3-one
AHFS/Drugs.comMonograph
MedlinePlusa682690
Pregnancy
category
  • X
Routes of
administration		By mouth[1]
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 80%[3]
MetabolismLiver (6β-hydroxylation, 5α- and 5β-reduction, 3α- and 3β-keto-oxidation, 11β-hydroxy-oxidation)[4]
Metabolites• 5α-Dihydrofluoxymesterone[4]
• 11-Oxofluoxymesterone[4]
Elimination half-life9.2 hours[5][6]
ExcretionUrine (<5% unchanged)[3][4]
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.875 Edit this at Wikidata
Chemical and physical data
FormulaC20H29FO3
Molar mass336.447 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:YLRFCQOZQXIBAB-RBZZARIASA-N checkY
  (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]

  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.
  3. ^ 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.
  4. ^ 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.
  5. ^ Cite error: The named reference Roberts2009 was invoked but never defined (see the help page).
  6. ^ Lemke TL, Williams DA (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1279–. ISBN 978-0-7817-6879-5.
  7. ^ Cite error: The named reference pmid22273746 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference pmid26074745 was invoked but never defined (see the help page).
  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.
  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.
  11. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).