5α-Pregnan-17α-ol-3,20-dione

5α-Pregnan-17α-ol-3,20-dione is a steroid and a metabolite of progesterone. It is also known as 5α-Pregnane-3,20-dione and is a naturally occurring progestogen related to progesterone. It is a white, crystalline solid that is practically insoluble in water and slightly soluble in alcohol.

Chemistry

5α-Pregnan-17α-ol-3,20-dione is a pregnane steroid and a derivative of progesterone. It has a double bond between the 5α and 6 positions and a keto group at the 3 and 20 positions. It is structurally related to other naturally occurring steroids such as cortisol, aldosterone, and testosterone.

Biosynthesis

5α-Pregnan-17α-ol-3,20-dione is synthesized from progesterone in the adrenal glands and the gonads. The conversion is catalyzed by the enzyme 5α-reductase, which reduces the double bond at the 4-5 position of progesterone.

Pharmacology

5α-Pregnan-17α-ol-3,20-dione has been found to have progestogenic activity, similar to that of its parent compound, progesterone. It has also been found to have some neurosteroid activity, acting as a potent positive allosteric modulator of the GABA_A receptor.

See also

• 5α-Dihydroprogesterone
• Allopregnanolone
• Pregnenolone

References

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