Androstenedione

from Wikipedia, the free encyclopedia
Structural formula
Structure of androstenedione
General
Non-proprietary name Androstenedione
other names

Androst-4-ene-3,17-dione

Molecular formula C 19 H 26 O 2
Brief description

colorless solid

External identifiers / databases
CAS number 63-05-8
EC number 200-554-5
ECHA InfoCard 100,000,504
PubChem 6128
DrugBank DB01536
Wikidata Q411064
Drug information
Drug class

Androgens

properties
Molar mass 286.41 g mol −1
Physical state

firmly

density

1.18 g cm −3

Melting point

170 ° C

solubility

almost insoluble in water (66 mg l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
08 - Dangerous to health 07 - Warning

danger

H and P phrases H: 302-351-360-362
P: 201-263-281-308 + 313
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Androstenedione (also Androstenedione ; English androstenedione ), abbreviated ASD , also called Andro or Andros in the bodybuilder scene , is a steroid made of nineteen carbon atoms (C-19) and a sex hormone , which is chemically similar to testosterone and belongs to the group of androgens ( 17- ketosteroid ). It is formed in the adrenal cortex (zona reticularis) and in the gonads , i.e. H. in women under the influence of the luteinizing hormone in the theca cell layer (stroma ovarii) surrounding the follicles and in the testicles in men. In the adult man, androstenedione is primarily formed in the testes; in the adult woman, about half of it is formed in the adrenal glands and the ovaries . Since it is formed as an intermediate product in testosterone and estradiol biosynthesis , from which testosterone or estrone (an estrogen ) can develop in the body, especially in fat cells, it is a hormone precursor and is therefore referred to as a pro-hormone. The exact physiological function of androstenedione is not yet fully known.

physiology

Androstenedione is produced from dehydroepiandrosterone (DHEA) with the help of the enzyme 3 β -hydroxysteroid dehydrogenase . It is reduced  to testosterone by means of testosterone 17 β dehydrogenase . Androstenedione is converted to estrone by aromatase .

Physiological fluctuations

The androstenedione concentration in the blood is subject to various fluctuations. Within a day (circadian rhythm) the highest values ​​are measured in the morning. The daily fluctuations are related to the release of the hormone ACTH. In women, the concentration is also cycle-dependent: here the highest values ​​are measured in the follicular phase of the female cycle.

Different concentrations in the plasma level are also observed within the human life cycle . In fetuses and newborns, the level is high, then decreases, and then increases again during puberty. It remains relatively constant in adulthood, only to decrease again with increasing age, especially in women after menopause . Androstenedione levels are increased during pregnancy.

Androstenedione plasma levels rise even after intense physical exertion.

pathology

Various pathological phenomena have an influence on the androstenedione plasma level.

Increased level in:

Low level in:

Medicines such as glucocorticoids or clomiphene can also lower the values.

Androstenedione as a "lifestyle" drug

Sports

The use of androstenedione to improve performance in athletes or in bodybuilding has been banned by the International Olympic Committee and other sports organizations. Androstenedione is on the doping list .

Androstenedione, which is said to stimulate the body's own testosterone production, is one of the most popular dietary supplements in the USA. Various studies, including those by manufacturers, have not found any permanent increase in testosterone levels, no increase in athletic performance, and no increase in muscle mass or other beneficial effects for athletes. A randomized double-blind study by Sonntag et al. Showed no significant effects of androstenedione on testosterone levels in middle-aged men over a period of 28 days. A study with young men that also included strength training effects found neither an increase in strength training effects nor in testosterone levels in 8 weeks. In addition to the ineffectiveness on adaptation effects in strength training, a possibly unfavorable reduction in the body's own testosterone synthesis could also be observed as a result of the androstenedione intake. The ineffectiveness with regard to a sporting benefit and the risks described below in the chapter side effects result in an unfavorable cost-benefit analysis for substitution in sport, even if sport ethical criteria are left out (doping).

Anti aging

Androstenedione is also used in the area of anti-aging . The effects in this field of application are not yet sufficiently known due to a lack of research. However, the data from the field of sport and side effects leave little room for well-founded substitution (see chapters above and below).

Side effects

In addition to a doping violation that athletes can commit with androstenedione, there are also studies that point to a lowering of HDL cholesterol levels with associated cardiovascular risks. Broeder et al. Found in their study that the blood lipid levels of the control group during the study period with regard to the cardiovascular risk were reduced by 12.3% due to training, while the androstenedione group showed a 10.5% increased risk. An influence on hormone-dependent tumors is also conceivable. In a single case, a young man who took androstenedione to "improve performance" was diagnosed with priapism . Due to the lack of long-term studies , little can be said about long-term side effects.

Doping in the GDR

From 1982 onwards, the preparation was used as part of the state compulsory doping in GDR competitive sports in preparation for competitions. One week before the championships, all anabolic steroids known to the doping committee were discontinued and replaced by androstenedione in order to bridge the anabolic-free phase until the test. The idea of ​​using androstenedione in competitive sport in the GDR arose at the Research Institute for Physical Culture and Sport . Kurt Schubert ( ZIMET ) Michael Oettel ( Jenapharm ) and Jürgen Hendel ( GERMED ) took part in a colloquium there in June 1981 .

literature

  • SG Beckham, CP Earnest: Four weeks of androstenedione supplementation diminishes the treatment response in middle aged men . In: British Journal of Sports Medicine . tape 37 , no. 2 , 2003, p. 212-218 , PMC 1724646 (free full text).
  • CE Broeder, J. Quindry, K. Brittingham, L. Panton, J. Thomson, S. Appakondu, K. Breuel, R. Byrd, J. Douglas, C. Earnest, C. Mitchell, M. Olson, T. Roy , C. Yarlagadda: The Andro Project: Physiological and hormonal influences of androstenedione supplementation in men 35 to 65 years old participating in a high-intensity resistance training program . In: Archives of Internal Medicines . tape 160 , no. 20 , 2000, pp. 3093-3104 ( full text ).
  • Douglas S. King, Rick L. Sharp, Matthew D. Vukovich, Gregory A. Brown, Tracy A. Reifenrath, Nathaniel L. Uhl, Kerry A. Parsons: Effect of Oral Androstenedione on Serum Testosterone and Adaptations to Resistance Training in Young Men . In: JAMA . tape 281 , 1999, p. 2020–2028 ( full text ).

Individual evidence

  1. a b c d e Entry on 4-androstene-3,17-dione in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  2. Data sheet 4-Androstene-3,17-dione from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).
  3. a b c d e f g Laborlexikon (Ed.): Androstendione. In: laborlexikon.de. July 26, 2008. Retrieved July 26, 2008 .
  4. a b c d Ulm University Hospital: Clinical Chemistry: Androstenedione. (No longer available online.) In: uniklinik-ulm.de. Formerly in the original ; Retrieved July 26, 2008 .  ( Page no longer available , search in web archivesInfo: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice.@1@ 2Template: Toter Link / www.uniklinik-ulm.de  
  5. a b c d S. L. Davison, R. Bell: Androgen physiology. In: Seminars in reproductive medicine. Volume 24, Number 2, April 2006, pp. 71-77. doi: 10.1055 / s-2006-939565 . PMID 16633980 .
  6. a b c Asker Jeukendrup, Michael Gleeson: Sport Nutrition. An Introduction to Energy Production and Performance . Human Kinetics, Champaign 2004, ISBN 0-7360-3404-8 , pp. 234 ff .
  7. ^ SG Beckham, CP Earnest: Four weeks of androstenedione supplementation diminishes the treatment response in middle aged men . In: British Journal of Sports Medicine . tape 37 , no. 2 , 2003, p. 212-218 , PMC 1724646 (free full text).
  8. Douglas S. King, Rick L. Sharp, Matthew D. Vukovich, Gregory A. Brown, Tracy A. Reifenrath, Nathaniel L. Uhl, Kerry A. Parsons: Effect of Oral Androstenedione on Serum Testosterone and Adaptations to Resistance Training in Young Men . In: JAMA . tape 281 , 1999, p. 2020–2028 ( ama-assn.org ).
  9. a b CE Broeder, J. Quindry, K. Brittingham, L. Panton, J. Thomson, S. Appakondu, K. Breuel, R. Byrd, J. Douglas, C. Earnest, C. Mitchell, M. Olson, T. Roy, C. Yarlagadda: The Andro Project: Physiological and hormonal influences of androstenedione supplementation in men 35 to 65 years old participating in a high-intensity resistance training program. In: Archives of Internal Medicines . tape 160 , no. 20 , 2000, pp. 3093-3104 ( ama-assn.org ).
  10. a b c d Alexander Lerchl, Friedrich Jockenhövel, Bruno Allolio: Hormones against aging - possibilities and limits . In: Deutsches Ärzteblatt . tape 98 , 2001, p. 31–32 ( aerzteblatt.de ).
  11. Wilfried Dubbels: Doping or harmless food supplements . In: pharmische-zeitung.de , accessed on January 31, 2017.
  12. ^ Klaus Latzel : State doping - The VEB Jenapharm in the sports system of the GDR. Cologne / Weimar 2009, chapter doping and the pharmaceutical industry of the GDR II, cooperation in the command economy - using the example of androstendione, p. 121ff.

Web links