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
ChEBI
ChemSpider
KEGG
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
C 25 H 38 O 8
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).
Chemical compound
Androsterone glucuronide (ADT-G ) is a major circulating and urinary metabolite of testosterone and dihydrotestosterone (DHT).[ 1] [ 1] androsterone by UDP-glucuronosyltransferases , with the major enzymes being UGT2B15 and UGT2B17 .[ 1] acne in women while androstanediol glucuronide is a marker of hirsutism (excess hair growth) in women.[ 2]
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] Liquid chromatography–mass spectrometry .[ 3] [ 4] [ 3]
Elevated levels of androsterone glucuronide in the blood have been observed in adult females who present with inflammatory acne.[ 5] Contraceptive by women who are affected with androsterone related acne can decrease the amount of inflammatory acne present.[ 5]
See also
References
^ a b c "Human Metabolome Database: Showing metabocard for Androsterone glucuronide (HMDB0002829)" .^ Jerome F. Strauss, III; Robert L. Barbieri (13 September 2013). Yen and Jaffe's Reproductive Endocrinology ISBN 978-1-4557-2758-2 ^ a b c 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 . ^ 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 . ^ a b 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 .
External links
