Adrenosterone

Last updated
Adrenosterone
Adrenosterone.png
Names
IUPAC name
Androst-4-ene-3,11,17-trione
Systematic IUPAC name
(3aS,3bS,9aR,9bS,11aS)-9a,11a-Dimethyl-2,3,3a,3b,4,5,8,9,9a,9b,11,11a-dodecahydro-1H-cyclopenta[a]phenanthrene-1,7,10-trione
Other names
Reichstein's substance G
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.222 OOjs UI icon edit-ltr-progressive.svg
MeSH Adrenosterone
PubChem CID
UNII
  • InChI=1S/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1 Yes check.svgY
    Key: RZRPTBIGEANTGU-IRIMSJTPSA-N Yes check.svgY
  • InChI=1/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1
    Key: RZRPTBIGEANTGU-IRIMSJTPBG
  • O=C4/C=C3/CC[C@@H]2[C@H](C(=O)C[C@@]1(C(=O)CC[C@H]12)C)[C@@]3(C)CC4
Properties
C19H24O3
Molar mass 300.39 g/mol
Melting point 222 °C (432 °F; 495 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Adrenosterone, also known as Reichstein's substance G , as well as 11-ketoandrostenedione (11-KA4), 11-oxoandrostenedione (11-OXO), and androst-4-ene-3,11,17-trione, is a steroid hormone with an extremely weak androgenic effect, and an intermediate/prohormone of 11-ketotestosterone. [1] It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichstein's substance G. Adrenosterone occurs in trace amounts in humans as well as most mammals and in larger amounts in fish, where it is a precursor to the primary androgen, 11-ketotestosterone. [2]

Adrenosterone is sold as a dietary supplement since 2007 as a fat loss and muscle gaining supplement. It is thought to be a competitive selective 11βHSD1 inhibitor, which is responsible for activation of cortisol from cortisone. [3] Thus preventing muscle breakdown, and contributing to a majority of its effects.

See also

Related Research Articles

<span class="mw-page-title-main">Nandrolone</span> Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

<span class="mw-page-title-main">Stanozolol</span> Discontinued steroid for heart treatment

Stanozolol, sold under many brand names, is an androgen and anabolic steroid (AAS) medication derived from dihydrotestosterone (DHT). It is used to treat hereditary angioedema. It was developed by American pharmaceutical company Winthrop Laboratories in 1962, and has been approved by the U.S. Food and Drug Administration for human use, though it is no longer marketed in the USA. It is also used in veterinary medicine. Stanozolol has mostly been discontinued, and remains available in only a few countries. It is given by mouth in humans or by injection into muscle in animals.

<span class="mw-page-title-main">Metandienone</span> Androgen and anabolic steroid

Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is still quite often used because of its affordability and effectiveness for bulking cycles. It is also used non-medically for physique- and performance-enhancing purposes. It is often taken by mouth.

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

Furazabol, also known as androfurazanol, is a synthetic, orally active anabolic-androgenic steroid which has been marketed in Japan since 1969. It is a 17α-alkylated derivative of dihydrotestosterone (DHT) and is closely related structurally to stanozolol, differing from it only by having a furazan ring system instead of pyrazole. Furazabol has a relatively high ratio of anabolic to androgenic activity. As with other 17α-alkylated AAS, it may have a risk of hepatotoxicity. The drug has been described as an antihyperlipidemic and is claimed to be useful in the treatment of atherosclerosis and hypercholesterolemia, but according to William Llewellyn, such properties of furazabol are a myth.

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

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth.

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

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

<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.

<span class="mw-page-title-main">11-Deoxycortisol</span> Chemical compound

11-Deoxycortisol, also known as cortodoxone (INN), cortexolone as well as 17α,21-dihydroxyprogesterone or 17α,21-dihydroxypregn-4-ene-3,20-dione, is an endogenous glucocorticoid steroid hormone, and a metabolic intermediate towards cortisol. It was first described by Tadeusz Reichstein in 1938 as Substance S, thus has also been referred to as Reichstein's Substance S or Compound S.

<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor. Anabolic steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance.

<span class="mw-page-title-main">11-Ketotestosterone</span> Chemical compound

11-Ketotestosterone (11-KT) is an oxidized form of testosterone that contains a keto group at the C11 position. It is related to adrenosterone, an androgen found in trace quantities in humans. In fish, 11-ketotestosterone functions as the endogenous androgenic sex hormone. In midshipman fish, 11-ketotestosterone is not present in females or Type II Males — Type II Males reach sexual maturation later, are less territorial, and have higher testosterone than Type I Males.

<span class="mw-page-title-main">11β-Hydroxyandrostenedione</span> Chemical compound

11β-Hydroxyandrostenedione (11β-OHA4), also known as 11β-hydroxyandrost-4-ene-3,17-dione, is an endogenous, naturally occurring steroid and androgen prohormone that is produced primarily, if not exclusively, in the adrenal glands. It is closely related to adrenosterone, 11-ketotestosterone (11-KT), and 11-ketodihydrotestosterone (11-KDHT), which are also produced in the adrenal glands.

<span class="mw-page-title-main">11-Ketodihydrotestosterone</span> Organic chemical compound

11-Ketodihydrotestosterone (11-KDHT), also known as 5α-androstan-17β-ol-3,11-dione, is an endogenous, naturally occurring steroid and androgen prohormone that is produced primarily, if not exclusively, in the adrenal glands. It is closely related to 11β-hydroxyandrostenedione (11β-KA4), adrenosterone, and 11-ketotestosterone (11-KT), which are also produced in the adrenal glands.

<span class="mw-page-title-main">21-Deoxycortisol</span> Chemical compound

21-Deoxycortisol, also known as 11β,17α-dihydroxyprogesterone or as 11β,17α-dihydroxypregn-4-ene-3,20-dione, is a naturally occurring, endogenous steroid related to cortisol (11β,17α,21-trihydroxyprogesterone) which is formed as a metabolite from 17α-hydroxyprogesterone via 11β-hydroxylase.

<span class="mw-page-title-main">11β-Hydroxyprogesterone</span> Chemical compound

11β-Hydroxyprogesterone (11β-OHP), also known as 21-deoxycorticosterone, as well as 11β-hydroxypregn-4-ene-3,20-dione, is a naturally occurring, endogenous steroid and derivative of progesterone. It is a potent mineralocorticoid. Syntheses of 11β-OHP from progesterone is catalyzed by the steroid 11β-hydroxylase (CYP11B1) enzyme, and, to a lesser extent, by the aldosterone synthase enzyme (CYP11B2).

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

Oxofluoxymesterone, or ketofluoxymesterone, is an androgen and anabolic steroid (AAS) which was never marketed. It was assessed in the treatment of breast cancer in women in the 1970s and showed effectiveness similar to that of other AAS. The drug is the 11-dehydrogenated analogue and a metabolite of fluoxymesterone.

The androgen backdoor pathway is a collective name for all metabolic pathways where clinically relevant androgens are synthesized from 21-carbon steroids (pregnanes) by their 5α-reduction with a roundabout of testosterone and/or androstenedione.

<span class="mw-page-title-main">11-Ketoandrosterone</span> Chemical compound

11-Ketoandrosterone is an endogenous steroid.

<span class="mw-page-title-main">11β-Hydroxytestosterone</span> Chemical compound

11β-Hydroxytestosterone is an endogenous steroid, a metabolite of testosterone. Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.

<span class="mw-page-title-main">GLPG-0492</span> Medication

GLPG-0492 (DT-200) is a drug which acts as a selective androgen receptor modulator (SARM). It has been investigated for the treatment of cachexia and muscular dystrophy.

References

  1. ↑ Pretorius, Elzette; Arlt, Wiebke; Storbeck, Karl-Heinz (2016). "A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids" (PDF). Molecular and Cellular Endocrinology. 441: 76–85. doi:10.1016/j.mce.2016.08.014. ISSN   0303-7207. PMID   27519632. S2CID   4079662.
  2. ↑ Blasco, M. N.; Carriquiriborde, P.; Marino, D. N.; Ronco, A. E.; Somoza, G. M. (2009). "A quantitative HPLC–MS method for the simultaneous determination of testosterone, 11-ketotestosterone and 11-β hydroxyandrostenedione in fish serum". Journal of Chromatography B. 877 (14–15): 1509–1515. doi:10.1016/j.jchromb.2009.03.028. PMID   19369122.
  3. ↑ Brooker L, Parr MK, Cawley A, Flenker U, Howe C, Kazlauskas R, Schänzer W, George A (2009). "Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control". Drug Test Anal. 1 (11–12): 587–95. doi:10.1002/dta.108. PMID   20355175.
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.