dihydrotestosterone
Also 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 papersArticle
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).