Structure via PubChem · Public domain (PubChem)
fluoxymesterone
Sign in to saveAlso known as Testosterone, 9-fluoro-11beta-hydroxy-17-methyl-, 9alpha-Fluoro-11beta-hydroxy-17-methyltestosterone, 9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one, 17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesterone, 11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one, 17α-Methyl-9α-fluoro-11β-hydroxytesterone, Fluoxymesteronum
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. It is taken by mouth.
Chemical data
- Formula
- C20H29FO3
- Molecular weight
- 336.4 g/mol
- 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
- 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
- InChIKey
- YLRFCQOZQXIBAB-RBZZARIASA-N
- XLogP
- 2.4
- Polar surface area
- 57.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1956
- Admin. routes
- oral
- Indications
- breast cancer, neoplasm, orchitis, hypogonadism
via ChEMBL · EBI
Research
489 papers- FLUOXYMESTERONE.Journal of the American Medical Association · 1957
- Fluoxymesterone-induced gynaecomastia in a patient with childhood aplastic anaemia.BMJ case reports · 2015
- Fluoxymesterone; a new oral androgen.British medical journal · 1959
- Fluoxymesterone ("halotestin"): a new androgen.The Medical journal of Australia · 1959
- Fluoxymesterone and the development of sexual behavior in the golden hamster.Developmental psychobiology · 1981
via PubMed
Wikidata facts
- Mass
- 336.21
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₀H₂₉FO₃
- medical condition treated
- hypogonadism
- isomeric 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
- canonical SMILES
- CC12CCC(=O)C=C1CCC3C2(C(CC4(C3CCC4(C)O)C)O)F
- World Health Organisation international non-proprietary name
- fluoxymesterone
- Commons category
- Fluoxymesterone
- defined daily dose
- 5
- physically interacts with
- androgen receptor
via Wikidata · CC0
~11 min read
Encyclopedic overview
21 sectionsContents
- Medical uses
- Available forms
- Non-medical uses
- Side effects
- Pharmacology
- Pharmacodynamics
- 11β-HSD inhibition
- Glucocorticoid activity
- Pharmacokinetics
- Chemistry
- Synthesis
- Detection in body fluids
- History
- Society and culture
- Generic names
- Brand names
- Availability
- United States
- Other countries
- Legal status
- References
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. It is taken by mouth.
Side effects of fluoxymesterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage and cardiovascular side effects like high blood pressure. 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). It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization.
Excerpted from Wikipedia’s “fluoxymesterone” article, available under the CC BY-SA 4.0 licence.