Structure via PubChem · Public domain (PubChem)
dihydrotestosterone
Sign in to saveAlso known as DHT, 5alpha-Dihydrotestosterone, 17beta-Hydroxy-5alpha-androstan-3-one, Androstanolone, Stanolone, 17β-hydroxy-5α-androstan-3-one, 17beta-Hydroxyandrostan-3-one
Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production of sebum and body hair composition.
Chemical data
- Formula
- C19H30O2
- Molecular weight
- 290.4 g/mol
- IUPAC name
- (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
- SMILES
- C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
- InChIKey
- NVKAWKQGWWIWPM-ABEVXSGRSA-N
- XLogP
- 3.7
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
15,537 papers- Dihydrotestosterone metabolism.Clinics in endocrinology and metabolism · 1986
- [5alpha-dihydrotestosterone (DHT)].Nihon rinsho. Japanese journal of clinical medicine · 2005
- Testosterone or dihydrotestosterone: what should be evaluated in hirsutism?Irish journal of medical science · 2023
- Is Dihydrotestosterone a Classic Hormone?Endocrine reviews · 2017
- Update on the use of trilostane in dogs.The Canadian veterinary journal = La revue veterinaire canadienne · 2018
via PubMed
Wikidata facts
- Mass
- 290.2245802
Show 4 more facts
- chemical formula
- C₁₉H₃₀O₂
- isomeric SMILES
- C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
- Commons category
- Dihydrotestosterone
- canonical SMILES
- O=C1CCC2(C)C(C1)CCC3C4CCC(O)C4(C)CCC32
via Wikidata · CC0
~25 min read
Article
16 sectionsContents
- Biological function
- 5α-Reductase 2 deficiency
- 5α-Reductase inhibitors
- Biological activity
- Biochemistry
- Biosynthesis
- Backdoor pathway
- Distribution
- Metabolism
- Excretion
- Levels
- Medical use
- Performance enhancement
- Chemistry
- History
- References
Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production of sebum and body hair composition.
The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues including the prostate gland, seminal vesicles, epididymides, skin, hair follicles, liver, and brain. This enzyme mediates reduction of the C4-5 double bond of testosterone. DHT may also be synthesized from progesterone and 17α-hydroxyprogesterone via the androgen backdoor pathway in the absence of testosterone. Relative to testosterone, DHT is considerably more potent as an agonist of the androgen receptor (AR).