Androsterone glucuronide

Last updated
Androsterone glucuronide
Androsterone glucuronide.svg
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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • 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
  • 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
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).

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]

Contents

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

References

  1. 1 2 3 "Human Metabolome Database: Showing metabocard for Androsterone glucuronide (HMDB0002829)".
  2. ↑ Jerome F. Strauss, III; Robert L. Barbieri (13 September 2013). Yen and Jaffe's Reproductive Endocrinology. Elsevier Health Sciences. pp. 837–. ISBN   978-1-4557-2758-2.
  3. 1 2 3 Labrie, Fernand; Bélanger, Alain; Bélanger, Patrick; Bérubé, René; Martel, Céline; Cusan, Leonello; Gomez, José; Candas, Bernard; Castiel, Isabelle; Chaussade, Véronique; Deloche, Claire; Leclaire, Jacques (2006-06-01). "Androgen glucuronides, instead of testosterone, as the new markers of androgenic activity in women". The Journal of Steroid Biochemistry and Molecular Biology. 99 (4): 182–188. doi:10.1016/j.jsbmb.2006.02.004. ISSN   0960-0760. PMID   16621522.
  4. ↑ Ke, Yuyong; Gonthier, Renaud; Isabelle, Maxim; Bertin, Jonathan; Simard, Jean-Nicolas; Dury, Alain Y.; Labrie, Fernand (2015-05-01). "A rapid and sensitive UPLC–MS/MS method for the simultaneous quantification of serum androsterone glucuronide, etiocholanolone glucuronide, and androstan-3α, 17β diol 17-glucuronide in postmenopausal women". The Journal of Steroid Biochemistry and Molecular Biology. 149: 146–152. doi:10.1016/j.jsbmb.2015.02.009. ISSN   0960-0760. PMID   25701608.
  5. 1 2 Carmina, E.; Godwin, A. J.; Stanczyk, F. Z.; Lippman, J. S.; Lobo, R. A. (2002-10-01). "The association of serum androsterone glucuronide with inflammatory lesions in women with adult acne1". Journal of Endocrinological Investigation. 25 (9): 765–768. doi:10.1007/BF03345509. ISSN   1720-8386.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.