Androsterone glucuronide

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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

Related Research Articles

<span class="mw-page-title-main">Androsterone</span> Endogenous steroid hormone

Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7 that of testosterone. Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstanedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.

<span class="mw-page-title-main">Dihydrotestosterone</span> Human hormone

Dihydrotestosterone is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production of sebum and body hair composition.

<span class="mw-page-title-main">Androstenediol</span> Chemical compound

Androstenediol, or 5-androstenediol, also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione).

<span class="mw-page-title-main">Etiocholanolone</span> Chemical compound

Etiocholanolone, also known as 5β-androsterone, as well as 3α-hydroxy-5β-androstan-17-one or etiocholan-3α-ol-17-one, is an etiocholane (5β-androstane) steroid as well as an endogenous 17-ketosteroid that is produced from the metabolism of testosterone. It causes fever, immunostimulation, and leukocytosis, and is used to evaluate adrenal cortex function, bone marrow performance, and in neoplastic disease to stimulate the immune system. Etiocholanolone is also known to be an inhibitory androstane neurosteroid, acting as a positive allosteric modulator of the GABAA receptor, and possesses anticonvulsant effects. The unnatural enantiomer of etiocholanolone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form.

<span class="mw-page-title-main">Ethisterone</span> Chemical compound

Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.

<span class="mw-page-title-main">Trestolone</span> Chemical compound

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

17β-Hydroxysteroid dehydrogenases, also 17-ketosteroid reductases (17-KSR), are a group of alcohol oxidoreductases which catalyze the reduction of 17-ketosteroids and the dehydrogenation of 17β-hydroxysteroids in steroidogenesis and steroid metabolism. This includes interconversion of DHEA and androstenediol, androstenedione and testosterone, and estrone and estradiol.

<span class="mw-page-title-main">Epiandrosterone</span> Chemical compound

Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.

<span class="mw-page-title-main">Androstanediol glucuronide</span> Chemical compound

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, and has been proposed as means of measuring androgenic activity.

<span class="mw-page-title-main">5β-Dihydrotestosterone</span> Chemical compound

5β-Dihydrotestosterone (5β-DHT), also known as 5β-androstan-17β-ol-3-one or as etiocholan-17β-ol-3-one, is an etiocholane (5β-androstane) steroid as well as an inactive metabolite of testosterone formed by 5β-reductase in the liver and bone marrow and an intermediate in the formation of 3α,5β-androstanediol and 3β,5β-androstanediol and, from them, respectively, etiocholanolone and epietiocholanolone. Unlike its isomer 5α-dihydrotestosterone, 5β-DHT either does not bind to or binds only very weakly to the androgen receptor. 5β-DHT is notable among metabolites of testosterone in that, due to the fusion of the A and B rings in the cis orientation, it has an extremely angular molecular shape, and this could be related to its lack of androgenic activity. 5β-DHT, unlike 5α-DHT, is also inactive in terms of neurosteroid activity, although its metabolite, etiocholanolone, does possess such activity.

<span class="mw-page-title-main">3α-Etiocholanediol</span> Chemical compound

3α-Etiocholanediol, or simply etiocholanediol, also known as 3α,5β-androstanediol or as etiocholane-3α,17β-diol, is a naturally occurring etiocholane (5β-androstane) steroid and an endogenous metabolite of testosterone. It is formed from 5β-dihydrotestosterone and is further transformed into etiocholanolone.

<span class="mw-page-title-main">Etiocholanolone glucuronide</span> Chemical compound

Etiocholanolone glucuronide (ETIO-G) is an endogenous, naturally occurring metabolite of testosterone. It is formed in the liver from etiocholanolone by UDP-glucuronyltransferases. ETIO-G has much higher water solubility than etiocholanolone and is eventually excreted in the urine via the kidneys. Along with androsterone glucuronide, it is one of the major inactive metabolites of testosterone.

<span class="mw-page-title-main">Testosterone glucuronide</span> Chemical compound

Testosterone glucuronide is an endogenous, naturally occurring steroid and minor urinary metabolite of testosterone.

<span class="mw-page-title-main">Testosterone sulfate</span> Chemical compound

Testosterone sulfate is an endogenous, naturally occurring steroid and minor urinary metabolite of testosterone.

Adrenal steroids are steroids that are derived from the adrenal glands. They include corticosteroids, which consist of glucocorticoids like cortisol and mineralocorticoids like aldosterone, adrenal androgens like dehydroepiandrosterone (DHEA), DHEA sulfate (DHEA-S), and androstenedione (A4), and neurosteroids like DHEA and DHEA-S, as well as pregnenolone and pregnenolone sulfate (P5-S). Adrenal steroids are specifically produced in the adrenal cortex.

<span class="mw-page-title-main">5α-Dihydroethisterone</span> Chemical compound

5α-Dihydroethisterone is an active metabolite of the formerly clinically used but now-discontinued progestin ethisterone and the experimental and never-marketed hormonal antineoplastic agent ethynylandrostanediol (HE-3235). Its formation from its parent drugs is catalyzed by 5α-reductase in tissues that express the enzyme in high amounts like the liver, skin, hair follicles, and prostate gland. 5α-DHET has significant affinity for steroid hormone receptors and may contribute importantly to the activities of its parent drugs.

<span class="mw-page-title-main">RU-57073</span> Chemical compound

RU-57073 is a nonsteroidal antiandrogen which was never marketed. It shows 163% of the affinity of testosterone for the androgen receptor and negligible affinity for other steroid hormone receptors.

<span class="mw-page-title-main">Androgen backdoor pathway</span> Series of interconnected biochemical reactions

The androgen backdoor pathway is responsible for the synthesis of physiologically relevant androgens. This process starts with 21-carbon steroids, also known as pregnanes, and involves a step called "5α-reduction". Notably, this pathway does not require the intermediate formation of testosterone, hence the term "bypassing testosterone" is sometimes used in medical literature as the hallmark feature of this way of androgen biosynthesis. This feature is a key distinction from the conventional, canonical androgenic pathway, which necessitates the involvement of testosterone as an intermediate in the synthesis of androgens.

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.
  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.
  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.


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