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.
Fluoxymesterone was first described in 1956 and was introduced for medical use in 1957. In addition to its medical use, fluoxymesterone is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.
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InChI=1S/C25H40O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-21,23,26-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1 |
GYNWSIBKBBWJJW-WWLGJQRMSA-N |
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O |
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Homo sapiens
(NCBI:txid9606)
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Found in
blood serum
(BTO:0000133).
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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Found in
urine
(BTO:0001419).
See:
PubMed
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human urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
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View more via ChEBI Ontology
Outgoing
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5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
(CHEBI:88730)
has functional parent
β-D-glucuronic acid
(CHEBI:28860)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
(CHEBI:88730)
has functional parent
5α-androstane-3α,17β-diol
(CHEBI:36713)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
(CHEBI:88730)
has role
human blood serum metabolite
(CHEBI:85234)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
(CHEBI:88730)
has role
human urinary metabolite
(CHEBI:84087)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
(CHEBI:88730)
is a
β-D-glucosiduronic acid
(CHEBI:15341)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
(CHEBI:88730)
is a
17β-hydroxy steroid
(CHEBI:35343)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
(CHEBI:88730)
is a
steroid glucosiduronic acid
(CHEBI:26763)
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17β-hydroxy-5α-androstan-3α-yl β-D-glucopyranosiduronic acid
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(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1-hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl β-D-glucopyranosiduronic acid
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ChEBI
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(3α,5α,17β)-17-hydroxyandrostan-3-yl β-D-glucopyranosiduronic acid
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ChEBI
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17-hydroxyandrostane-3-glucuronoside
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ChemIDplus
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17β-hydroxy-5α-androstan-3α-yl glucosiduronic acid
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ChEBI
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3α-androstanediol glucuronide
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ChEBI
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3α-diolG
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ChEBI
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5α-androstan-3α,17β-diol-O-3-β-glucuronic acid
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ChEBI
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Adiol 3-G
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ChemIDplus
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androstanediol glucuronide
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ChEBI
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65535-18-4
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CAS Registry Number
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ChemIDplus
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10438402
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PubMed citation
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Europe PMC
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10778119
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PubMed citation
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Europe PMC
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1564146
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Europe PMC
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16149550
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Europe PMC
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16979812
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1835405
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Europe PMC
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1846006
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Europe PMC
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20960816
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Europe PMC
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22624806
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Europe PMC
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2534065
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PubMed citation
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Europe PMC
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25667596
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PubMed citation
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Europe PMC
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29523115
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PubMed citation
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Europe PMC
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30625341
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PubMed citation
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Europe PMC
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31275280
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Europe PMC
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3217954
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PubMed citation
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Europe PMC
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3335605
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3521957
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PubMed citation
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Europe PMC
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7952161
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PubMed citation
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Europe PMC
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7980317
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PubMed citation
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Europe PMC
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8005308
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PubMed citation
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Europe PMC
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8236331
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PubMed citation
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Europe PMC
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8287530
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PubMed citation
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Europe PMC
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8463546
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PubMed citation
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Europe PMC
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8886824
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PubMed citation
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Europe PMC
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9186820
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PubMed citation
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Europe PMC
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9258802
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PubMed citation
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Europe PMC
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9578510
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PubMed citation
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Europe PMC
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