Androsterone glucuronide

Androsterone glucuronide (ADT-G) is a major circulating and urinary metabolite of testosterone and dihydrotestosterone (DHT).^[1] It accounts for 93% of total androgen glucuronides in women.^[1] ADT-G is formed from androsterone by UDP-glucuronosyltransferases, with the major enzymes being UGT2B15 and UGT2B17.^[1] It is a marker of acne in women while androstanediol glucuronide is a marker of hirsutism (excess hair growth) in women.^[2]

Androsterone glucuronide

Names
IUPAC name 17-Oxo-5α-androstan-3α-yl β-D-glucopyranosiduronic acid
Systematic IUPAC name (2S,3S,4S,5R,6R)-6-{[(3aS,3bR,5aS,7R,9aS,9bS,11aS)-9a,11a-Dimethyl-1-oxohexadecahydro-1H-cyclopenta[a]pheananthren-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Other names ADT-G; 5α-Androstan-3α-ol-17-one 3-glucuronide
Identifiers
CAS Number	1852-43-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28832
ChemSpider	102793
KEGG	C11135
PubChem CID	114833
UNII	IMD4XD0W3U Y
CompTox Dashboard (EPA)	DTXSID80862764
InChI InChI=1S/C25H38O8/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/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1 Key: VFUIRAVTUVCQTF-BSOWLZGZSA-N
SMILES C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
Properties
Chemical formula	C25H38O8
Molar mass	466.571 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Relevance in women's health

Quantification of ADT-G and 3α-diol-G levels in Serum (blood) is an effective means of assessing androgen content in blood and androgenic activity in women.^[3]  Androsterone glucuronide content can be estimated using Liquid chromatography–mass spectrometry.^[3][4] If an unusual level of ADT-G is observed in the blood (either an elevated or decreased amount), proper treatment plans can be developed in order to treat related symptoms.^[3]

Elevated levels of androsterone glucuronide in the blood have been observed in adult females who present with inflammatory acne.^[5]  The introduction of therapeutic antiandrogen treatment and the use of an oral Contraceptive by women who are affected with androsterone related acne can decrease the amount of inflammatory acne present.^[5]

See also

• 3α-Androstanediol
• Androsterone sulfate
• Etiocholanolone glucuronide