5α-androstanedione
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Androstanedione, also known as 5α-androstanedione or as 5α-androstane-3,17-dione, is a
naturally occurring A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical ...
androstane (5α-androstane)
steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...
and an endogenous metabolite of
androgen An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes ...
s like
testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...
, dihydrotestosterone (DHT), dehydroepiandrosterone (DHEA), and androstenedione. It is the C5 epimer of etiocholanedione (5β-androstanedione). Androstanedione is formed from androstenedione by 5α-reductase and from DHT by 17β-hydroxysteroid dehydrogenase. It has some
androgen An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes ...
ic activity. In female genital skin, the conversion of androstenedione into DHT through 5α-androstanedione appears to be more important than the direct conversion of testosterone into DHT.


References


External links


Androstanedione (HMDB0000899) - Human Metabolome Database
5α-Reduced steroid metabolites Anabolic–androgenic steroids Androstanes Diketones Steroid hormones {{Biochemistry-stub