:Androsterone glucuronide
{{Chembox
| ImageFile = Androsterone glucuronide.svg
| ImageSize = 250px
| ImageAlt =
| IUPACName = 17-Oxo-5α-androstan-3α-yl β-D-glucopyranosiduronic acid
| SystematicName = (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
| OtherNames = ADT-G; 5α-Androstan-3α-ol-17-one 3-glucuronide
| Section1 = {{Chembox Identifiers
| CASNo = 1852-43-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = IMD4XD0W3U
| ChEBI = 28832
| ChEMBL =
| ChemSpiderID = 102793
| KEGG = C11135
| PubChem = 114833
| StdInChI = 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
| StdInChIKey = 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
}}
| Section2 = {{Chembox Properties
| C=25 | H=38 | O=8
| MolarMass = 466.571 g/mol
| Appearance =
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| Section3 = {{Chembox Hazards
| MainHazards =
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Androsterone glucuronide (ADT-G) is a major circulating and urinary metabolite of testosterone and dihydrotestosterone (DHT).{{Cite web|url=http://www.hmdb.ca/metabolites/HMDB02829|title = Human Metabolome Database: Showing metabocard for Androsterone glucuronide (HMDB0002829)}} It accounts for 93% of total androgen glucuronides in women. ADT-G is formed from androsterone by UDP-glucuronosyltransferases, with the major enzymes being UGT2B15 and UGT2B17. It is a marker of acne in women while androstanediol glucuronide is a marker of hirsutism (excess hair growth) in women.{{cite book|author1=Jerome F. Strauss, III|author2=Robert L. Barbieri|title=Yen and Jaffe's Reproductive Endocrinology|url=https://books.google.com/books?id=KZ95AAAAQBAJ&pg=PA837|date=13 September 2013|publisher=Elsevier Health Sciences|isbn=978-1-4557-2758-2|pages=837–}}
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.{{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=2006-06-01 |title=Androgen glucuronides, instead of testosterone, as the new markers of androgenic activity in women |url=https://www.sciencedirect.com/science/article/abs/pii/S0960076006000598 |journal=The Journal of Steroid Biochemistry and Molecular Biology |volume=99 |issue=4 |pages=182–188 |doi=10.1016/j.jsbmb.2006.02.004 |pmid=16621522 |issn=0960-0760|url-access=subscription }} Androsterone glucuronide content can be estimated using Liquid chromatography–mass spectrometry.{{Cite journal |last1=Ke |first1=Yuyong |last2=Gonthier |first2=Renaud |last3=Isabelle |first3=Maxim |last4=Bertin |first4=Jonathan |last5=Simard |first5=Jean-Nicolas |last6=Dury |first6=Alain Y. |last7=Labrie |first7=Fernand |date=2015-05-01 |title=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 |url=https://www.sciencedirect.com/science/article/abs/pii/S0960076015000473 |journal=The Journal of Steroid Biochemistry and Molecular Biology |volume=149 |pages=146–152 |doi=10.1016/j.jsbmb.2015.02.009 |pmid=25701608 |issn=0960-0760|url-access=subscription }} 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.
Elevated levels of androsterone glucuronide in the blood have been observed in adult females who present with inflammatory acne.{{Cite journal |last1=Carmina |first1=E. |last2=Godwin |first2=A. J. |last3=Stanczyk |first3=F. Z. |last4=Lippman |first4=J. S. |last5=Lobo |first5=R. A. |date=2002-10-01 |title=The association of serum androsterone glucuronide with inflammatory lesions in women with adult acne1 |url=https://link.springer.com/article/10.1007/BF03345509 |journal=Journal of Endocrinological Investigation |language=en |volume=25 |issue=9 |pages=765–768 |doi=10.1007/BF03345509 |issn=1720-8386|url-access=subscription }} 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.
See also
References
{{Reflist|30em}}
External links
- [http://www.hmdb.ca/metabolites/HMDB02829 Metabocard for Androsterone Glucuronide (HMDB02829) – Human Metabolome Database]
{{Steroid hormones}}