Androstanediol glucuronide

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{{Chembox

| ImageFile = Androstanediol glucuronide.svg

| ImageSize = 200px

| IUPACName = 17β-Hydroxy-5α-androstan-3α-yl β-D-glucopyranosiduronic acid

| SystematicName = (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

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|Section1={{Chembox Identifiers

| CASNo = 65535-18-4

| PubChem = 16727166

| ChemSpiderID = 20558912

| SMILES = C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O

| InChI = 1/C25H40O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-21,23,26-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1

| InChIKey = GYNWSIBKBBWJJW-WWLGJQRMBJ

| StdInChI = 1S/C25H40O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-21,23,26-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1

| StdInChIKey = GYNWSIBKBBWJJW-WWLGJQRMSA-N

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|Section2={{Chembox Properties

| C=25 | H=40 | O=8

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|Section3={{Chembox Hazards

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{{technical|date=December 2014}}

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 dihydrotestosterone,{{cite journal |vauthors=Moghissi E, Ablan F, Horton R |title=Origin of plasma androstanediol glucuronide in men |journal=The Journal of Clinical Endocrinology and Metabolism |volume=59 |issue=3 |pages=417–21 | date=September 1984 |pmid=6746859 |doi=10.1210/jcem-59-3-417}} and has been proposed as means of measuring androgenic activity.

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.{{cite journal |vauthors=Vermeulen A, Giagulli VA |title=Physiopathology of plasma androstanediol-glucuronide |journal=The Journal of Steroid Biochemistry and Molecular Biology |volume=39 |issue=5B |pages=829–33 | date=November 1991 |pmid=1835405|doi=10.1016/0960-0760(91)90032-z |s2cid=46135916 }}

3α-ADG is used as a marker of target tissue cellular action.{{cite journal |last1=Labrie |first1=Fernand |last2=Bélanger |first2=Alain |last3=Bélanger |first3=Patrick |last4=Bérubé |first4=René |last5=Martel |first5=Céline |last6=Cusan |first6=Leonello |last7=Gomez |first7=José |last8=Candas |first8=Bernard |last9=Castiel |first9=Isabelle |last10=Chaussade |first10=Véronique |last11=Deloche |first11=Claire |last12=Leclaire |first12=Jacques |date=June 2006 |title=Androgen glucuronides, instead of testosterone, as the new markers of androgenic activity in women |url=https://linkinghub.elsevier.com/retrieve/pii/S0960076006000598 |journal=The Journal of Steroid Biochemistry and Molecular Biology |language=en |volume=99 |issue=4–5 |pages=182–188 |doi=10.1016/j.jsbmb.2006.02.004|pmid=16621522 |s2cid=31765384 |url-access=subscription }} 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.