Androsterone

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Androsterone
Skeletal formula of androsterone
Ball-and-stick model of the androsterone molecule
Systematic (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
Identifiers
CAS Number 53-41-8 YesY
ATC code none
PubChem CID: 5879
ChemSpider 5668 YesY
UNII C24W7J5D5R YesY
ChEBI CHEBI:16032 YesY
ChEMBL CHEMBL87285 YesY
Chemical data
Formula C19H30O2
Molecular mass 290.440 g/mol
  • O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@H](O)CC[C@]34C)C
  • InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1 YesY
  • Key:QGXBDMJGAMFCBF-HLUDHZFRSA-N YesY
  (verify)

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Not to be confused with androstenone.

Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone.[1] It is a weak androgen with a potency that is approximately 1/7th that of testosterone.[2] In addition, it can be converted to dihydrotestosterone (DHT) from 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstenedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.[3][4] Androsterone is also known to be an inhibitory androstane neurosteroid,[5][6] acting as a positive allosteric modulator of the GABAA receptor,[7] and possesses anticonvulsant effects.[8] The unnatural enantiomer of androsterone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form. [9] Androsterone's 3β-isomer is epiandrosterone, and its 5β-epimer is etiocholanolone.

History

It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 liters (3,700 imp gal; 4,500 U.S. gal) of male urine, from which they got 50 milligrams (0.77 gr) of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.

Sources

Androsterone has been shown to naturally occur in pine pollen and is well known in many animal species.[10]

Biological role

Androsterone is generally considered to be an inactive metabolite of testosterone, which when conjugated by glucuronidation and sulfation allows testosterone to be removed from the body, but it is a weak neurosteroid that can cross into the brain and could have effects on brain function.[8]

Pheromone

Androsterone is found in the human axilla and skin as well as in the urine.[11] It may also be secreted by human sebaceous glands.[11] It is described as having a musky odor similar to that of androstenol.[11] Androsterone has been found to affect human behavior when smelled.[11]

Bioynthesis

Androsterone and its 5β-isomer, etiocholanolone, are produced in the body as metabolites of testosterone. Testosterone is converted to 5α-dihydrotestosterone and 5β-dihydrotestosterone by 5α-reductase and 5β-reductase, respectively. The enzyme 3α-hydroxysteroid dehydrogenase converts the reduced forms to 5α-androstanediol and 5β-androstanediol, which are subsequently converted by 17β-hydroxysteroid dehydrogenase to androsterone and etiocholanolone, respectively. Androsterone and etiocholanolone can also be formed from androstenedione via the action of 5α-reductase and 5β-reductase forming 5α-androstanedione and 5β-androstanedione which are then converted to androsterone and etiocholanolone by 3α-hydroxysteroid dehydrogenase and 3β-hydroxysteroid dehydrogenase, respectively.[8]

See also

References

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External links


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