Chemistry:Androstanediol glucuronide
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| IUPAC name
17β-Hydroxy-5α-androstan-3α-yl β-D-glucopyranosiduronic acid
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| Systematic IUPAC name
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1-hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}oxane-2-carboxylic acid | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C25H40O8 | |
| Molar mass | 468.587 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
3α-Androstanediol glucuronide (3α-ADG) is a metabolite formed from human androgens; compounds involved in the development and maintenance of sexual characteristics. It is formed by the glucuronidation of both dihydrotestosterone and testosterone,[1] and has been proposed as means of measuring androgenic activity.[2]
In women the adrenal steroids, dehydroepiandrosterone sulfate, androstenedione and dehydroepiandrosterone are the major precursors of plasma 3α-ADG, accounting for almost the totality of circulating 3α-ADG. Levels of 3α-ADG decrease significantly with age.[3]
3α-ADG is used as a marker of target tissue cellular action.[4] 3α-ADG correlates with level of 5α-reductase activity (testosterone and 3α-androstanediol to dihydrotestosterone) in the skin. Concentrations of 3α-ADG are associated with the level of cutaneous androgen metabolism.
See also
References
- ↑ "Origin of plasma androstanediol glucuronide in men". The Journal of Clinical Endocrinology and Metabolism 59 (3): 417–21. September 1984. doi:10.1210/jcem-59-3-417. PMID 6746859.
- ↑ Labrie, Fernand; Bélanger, Alain; Bélanger, Patrick; Bérubé, René; Martel, Céline; Cusan, Leonello; Gomez, José; Candas, Bernard et al. (June 2006). "Androgen glucuronides, instead of testosterone, as the new markers of androgenic activity in women". The Journal of Steroid Biochemistry and Molecular Biology 99 (4–5): 182–188. doi:10.1016/j.jsbmb.2006.02.004. PMID 16621522.
- ↑ "Physiopathology of plasma androstanediol-glucuronide". The Journal of Steroid Biochemistry and Molecular Biology 39 (5B): 829–33. November 1991. doi:10.1016/0960-0760(91)90032-z. PMID 1835405.
- ↑ Labrie, Fernand; Bélanger, Alain; Bélanger, Patrick; Bérubé, René; Martel, Céline; Cusan, Leonello; Gomez, José; Candas, Bernard et al. (June 2006). "Androgen glucuronides, instead of testosterone, as the new markers of androgenic activity in women" (in en). The Journal of Steroid Biochemistry and Molecular Biology 99 (4–5): 182–188. doi:10.1016/j.jsbmb.2006.02.004. PMID 16621522. https://linkinghub.elsevier.com/retrieve/pii/S0960076006000598.
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