Английская Википедия:5α-Pregnane-3α,17α-diol-20-one

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Файл:17-alpha-hydroxyallopregnanolone-comparison-3-pregnanes.svg
Comparison of chemical structures for allopregnane, allopregnanolone and 5α-Pregnane-3α,17α-diol-20-one (17α-allopregnanolone). Please note that the difference between the allopregnanolone and 5α-Pregnane-3α,17α-diol-20-one is a hydroxyl function group (−OH) at C17 position.
Complex chemical diagram
Structure of cholestane, a steroid with 27 carbon atoms. Its core ring system (ABCD), composed of 17 carbon atoms, is shown with IUPAC-approved ring lettering and atom numbering.

5α-Pregnane-3α,17α-diol-20-one, also known as 17α-hydroxyallopregnanolone (17-OH-allo) is an endogenous steroid.

Function

5α-Pregnane-3α,17α-diol-20-one is a metabolite, an intermediate product within the androgen backdoor pathway[1] in which 17α-hydroxyprogesterone (17‐OHP) is 5α-reduced and finally converted to 5α-dihydrotestosterone (DHT) without testosterone as a metabolic intermediate.[2][3]

The pathway can be outlined as 17-OHP → 5α-pregnan-17α-ol-3,20-dione5α-pregnane-3α,17α-diol-20-oneandrosterone5α-androstane-3α,17β-diol → DHT.[4][5][6]

Biosynthesis

5α-Pregnane-3α,17α-diol-20-one is produced from 5α-pregnan-17α-ol-3,20-dione[7] in a reaction catalyzed by a reductive 3α-hydroxysteroid dehydrogenase (3α-HSD),[8] i.e. by the two aldo-keto reductase isozymes: AKR1C2 and AKR1C4,[9] and by 17β-hydroxysteroid dehydrogenase 6 (HSD17B6) that also has the 3α-HSD activity.[9]

See also

References

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