androsterone
Also known as cis-androsterone, (3alpha,5alpha)-3-hydroxyandrostan-17-one, 5alpha-androsterone, Androtine, Androkinine, 5alpha-androstane-3alpha-ol-17-one, 3-epihydroxyetioallocholan-17-one, (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7 that of testosterone. Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstanedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.
Key facts
- Drug.PubChem
- 5879
- Drug.ATC_prefix
- none
- Drug.ChEMBL
- 87285
- Drug.verifiedrevid
- 457130388
- Drug.IUPAC_name
- (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
- Drug.image
- androsteron.svg
- Drug.image_class
- skin-invert-image
- Drug.alt
- Skeletal formula of androsterone
- Drug.width
- 210
- Drug.image2
- Androsterone-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of the androsterone molecule
Article
11 sectionsContents
- Biological function
- Pheromone
- Biochemistry
- Biosynthesis
- Metabolism
- Chemistry
- Sources
- History
- See also
- References
- External links
Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7 that of testosterone. Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstanedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.
Androsterone is also known to be an inhibitory androstane neurosteroid, acting as a positive allosteric modulator of the GABAA receptor, and possesses anticonvulsant effects. The unnatural enantiomer of androsterone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form. Androsterone's 3β-isomer is epiandrosterone, and its 5β-epimer is etiocholanolone. The 3β,5β-isomer is epietiocholanolone.