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Testosterone, DHT, and Nandrolone conversions to other anabolic steroids[1]

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Testosterone Derivatives and Reactions

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Testosterone Conversion to DHT[2], Nandrolone[3], Dianabol[4], Turinabol[5], Halotestin[6], and Equipoise[7]

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Red arrows show molecular differences from testosterone conversion to 6 different anabolic steroids.

DHT Conversion to Winstrol[8], Primobolan[9], Anadrol[10], and Superdrol[11]

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Red arrows show molecular differences from DHT conversion to 4 different anabolic steroids.

Nandrolone Conversion to Trestolone[12], Trenbolone[13], Norboletone[14], and Ethylnandrol[15]

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Red arrows show molecular differences from Nandrolone conversion to 4 different anabolic steroids.

Mechanism of action
See also: Steroid hormone

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The human androgen receptor bound to testosterone[16] The protein is shown as a ribbon diagram in red, green, and blue, with the steroid shown in white.

The pharmacodynamics of AAS are unlike peptide hormones. Water-soluble peptide hormones cannot penetrate the fatty cell membrane and only indirectly affect the nucleus of target cells through their interaction with the cell's surface receptors. However, as fat-soluble hormones, AAS are membrane-permeable and influence the nucleus of cells by direct action. The pharmacodynamic action of AAS begin when the exogenous hormone penetrates the membrane of the target cell and binds to an androgen receptor (AR) located in the cytoplasm of that cell. From there, the compound hormone-receptor diffuses into the nucleus, where it either alters the expression of genes[17] or activates processes that send signalsto other parts of the cell.[18] Different types of AAS bind to the AAR with different affinities, depending on their chemical structure.[19]

The effect of AAS on muscle mass is caused in at least two ways:[20] first, they increase the production of proteins; second, they reduce recovery time by blocking the effects of stress hormone cortisol on muscle tissue, so that catabolism of muscle is greatly reduced. It has been hypothesized that this reduction in muscle breakdown may occur through AAS inhibiting the action of other steroid hormones called glucocorticoids that promote the breakdown of muscles.[21] AAS also affect the number of cells that develop into fat-storage cells, by favouring cellular differentiation into muscle cells instead.[22]

Molecular Interaction of AAS with Androgen Receptors

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Anabolic steroids interact at a molecular level with ARs across various tissues, including muscle, bone, and reproductive systems.[23] Upon binding to the AR, anabolic steroids trigger a translocation of the hormone-receptor complex to the cell nucleus, where they either alter gene expression or activate cellular signaling pathways; this results in increased protein synthesis, enhanced muscle growth, and reduced muscle catabolism.[24]

Additionally, anabolic steroids influence cellular differentiation, favoring the development of muscle cells over fat-storage cells[25]. Research in this field has shown that the structural modifications in anabolic steroids are critical in determining their binding affinity to ARs and their resulting anabolic and androgenic activities[26]. These modifications affect the steroids' ability to influence gene expression and cellular processes, highlighting the complex biophysical interactions of anabolic steroids at the cellular level[27].

  1. ^ Kicman, A T (2008-06). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. ISSN 0007-1188. PMC 2439524. PMID 18500378. {{cite journal}}: Check date values in: |date= (help)CS1 maint: PMC format (link)
  2. ^ academic.oup.com. doi:10.1093/jnci/djm323. PMC 6126902. PMID 18230794 https://academic.oup.com/crawlprevention/governor?content=%2fjnci%2farticle-lookup%2fdoi%2f10.1093%2fjnci%2fdjm323. Retrieved 2023-12-09. {{cite web}}: Missing or empty |title= (help)CS1 maint: PMC format (link)
  3. ^ Kicman, A T (2008-06). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. ISSN 0007-1188. PMC 2439524. PMID 18500378. {{cite journal}}: Check date values in: |date= (help)CS1 maint: PMC format (link)
  4. ^ Meystre, Ch.; Frey, H.; Voser, W.; Wettstein, A. (1956-01). "Gewinnung von 1;4‐Bisdehydro‐3‐oxo‐steroiden. Über Steroide, 139. Mitteilung". Helvetica Chimica Acta. 39 (3): 734–742. doi:10.1002/hlca.19560390314. ISSN 0018-019X. {{cite journal}}: Check date values in: |date= (help)
  5. ^ Kaufmann, Günter; Schumann, Gertrud; Hörhold, Cläre (1986-10-01). "Influence of 1-double bond and 11β-hydroxy group on stereospecific microbial reductions of 4-en-3-oxo-steroids". Journal of Steroid Biochemistry. 25 (4): 561–566. doi:10.1016/0022-4731(86)90403-6. ISSN 0022-4731.
  6. ^ Stanley, S. M. R; Kent, S; Rodgers, J. P (1997-12-19). "Biotransformation of 17-alkyl steroids in the equine: high-performance liquid chromatography–mass spectrometric and gas chromatography–mass spectrometric analysis of fluoxymesterone metabolites in urine samples". Journal of Chromatography B: Biomedical Sciences and Applications. 704 (1): 119–128. doi:10.1016/S0378-4347(97)00440-4. ISSN 0378-4347.
  7. ^ Alm-Eldeen, A; Tousson, E (2012-05). "Deterioration of glomerular endothelial surface layer and the alteration in the renal function after a growth promoter boldenone injection in rabbits". Human & Experimental Toxicology. 31 (5): 465–472. doi:10.1177/0960327111420745. ISSN 0960-3271. {{cite journal}}: Check date values in: |date= (help)
  8. ^ Clinton, R. O.; Manson, A. J.; Stonner, F. W.; Beyler, A. L.; Potts, G. O.; Arnold, Aaron (1959-03). "STEROIDAL [3,2-c]PYRAZOLES". Journal of the American Chemical Society. 81 (6): 1513–1514. doi:10.1021/ja01515a060. ISSN 0002-7863. {{cite journal}}: Check date values in: |date= (help)
  9. ^ Bonnecaze, Alex K.; O’Connor, Thomas; Burns, Cynthia A. (2021-07-01). "Harm Reduction in Male Patients Actively Using Anabolic Androgenic Steroids (AAS) and Performance-Enhancing Drugs (PEDs): a Review". Journal of General Internal Medicine. 36 (7): 2055–2064. doi:10.1007/s11606-021-06751-3. ISSN 1525-1497. PMC 8298654. PMID 33948794.{{cite journal}}: CS1 maint: PMC format (link)
  10. ^ Ringold, H. J.; Batres, E.; Halpern, O.; Necoechea, E. (1959-01). "Steroids. CV.1 2-Methyl and 2-Hydroxymethylene-androstane Derivatives". Journal of the American Chemical Society. 81 (2): 427–432. doi:10.1021/ja01511a040. ISSN 0002-7863. {{cite journal}}: Check date values in: |date= (help)
  11. ^ De Brabanter, Nik; Van Gansbeke, Wim; Geldof, Lore; Van Eenoo, Peter (2012-11). "An improved gas chromatography screening method for doping substances using triple quadrupole mass spectrometry, with an emphasis on quality assurance". Biomedical Chromatography. 26 (11): 1416–1435. doi:10.1002/bmc.2714. ISSN 0269-3879. {{cite journal}}: Check date values in: |date= (help)
  12. ^ Counsell, R. E.; Klimstra, P. D.; Colton, F. B. (1962-01). "Anabolic Agents. Derivatives of 5α-Androst-1-ene". The Journal of Organic Chemistry. 27 (1): 248–253. doi:10.1021/jo01048a060. ISSN 0022-3263. {{cite journal}}: Check date values in: |date= (help)
  13. ^ Lu, Frank C.; Rendel, Jan; Abou Akkada, Abdelkader Rached; Nations, Food and Agriculture Organization of the United; Organization, World Health; FAO/WHO Symposium on Anabolic Agents in Animal Production (1975  : Rome, Italy) (1976). Anabolic agents in animal production : FAO/WHO Symposium, Rome, March 1975. Stuttgart : Thieme. ISBN 978-3-13-536101-7.{{cite book}}: CS1 maint: numeric names: authors list (link)
  14. ^ Catlin, Don H.; Ahrens, Brian D.; Kucherova, Yulia (2002-06-05). "Detection of norbolethone, an anabolic steroid never marketed, in athletes' urine". Rapid Communications in Mass Spectrometry. 16 (13): 1273–1275. doi:10.1002/rcm.722. ISSN 0951-4198.
  15. ^ Camerino, B.; Sciaky, R. (1975-01-01). "Structure and effects of anabolic steroids". Pharmacology & Therapeutics. Part B: General and Systematic Pharmacology. 1 (2): 233–275. doi:10.1016/0306-039X(75)90007-0. ISSN 0306-039X.
  16. ^ Pereira de Jésus-Tran K, Côté PL, Cantin L, Blanchet J, Labrie F, Breton R (2006). "Comparison of crystal structures of human androgen receptor ligand-binding domain complexed with various agonists reveals molecular determinants responsible for binding affinity". Protein Sci. 15 (5): 987–99. doi:10.1110/ps.051905906. PMC 2242507. PMID 16641486.
  17. ^ Lavery DN, McEwan IJ (2005). "Structure and function of steroid receptor AF1 transactivation domains: induction of active conformations". Biochem. J. 391 (Pt 3): 449–64. doi:10.1042/BJ20050872. PMC 1276946. PMID 16238547.
  18. ^ Cheskis BJ (2004). "Regulation of cell signalling cascades by steroid hormones". J. Cell. Biochem. 93 (1): 20–7. doi:10.1002/jcb.20180. PMID 15352158. S2CID 43430651.
  19. ^ Hartgens F, Kuipers H (2004). "Effects of androgenic-anabolic steroids in athletes". Sports Med. 34 (8): 513–54. doi:10.2165/00007256-200434080-00003. PMID 15248788. S2CID 15234016.
  20. ^ Brodsky IG, Balagopal P, Nair KS (1996). "Effects of testosterone replacement on muscle mass and muscle protein synthesis in hypogonadal men—a clinical research center study". J. Clin. Endocrinol. Metab. 81 (10): 3469–75. doi:10.1210/jcem.81.10.8855787. PMID 8855787.
  21. ^ Hickson RC, Czerwinski SM, Falduto MT, Young AP (1990). "Glucocorticoid antagonism by exercise and androgenic-anabolic steroids". Medicine & Science in Sports & Exercise. 22 (3): 331–40. doi:10.1249/00005768-199006000-00010. PMID 2199753.
  22. ^ Singh R, Artaza JN, Taylor WE, Gonzalez-Cadavid NF, Bhasin S (2003). "Androgens stimulate myogenic differentiation and inhibit adipogenesis in C3H 10T1/2 pluripotent cells through an androgen receptor-mediated pathway". Endocrinology. 144 (11): 5081–8. doi:10.1210/en.2003-0741. PMID 12960001.
  23. ^ Heinlein, Cynthia (1 April 2004). "Androgen Receptor in Prostate Cancer". Endocrine Reviews. 25 (2): 276–308 – via Oxford Academic.
  24. ^ RIGGS, B. LAWRENCE (June 2002). "Sex Steroids and the Construction and Conservation of the Adult Skeleton" (PDF). The Endocrine Society. 23 (3): 279–302.
  25. ^ Azziz, Ricardo (October 23, 2008). "The Androgen Excess and PCOS Society criteria for the polycystic ovary syndrome: the complete task force report". Fertility and Sterility. 91 (2): 456–488.
  26. ^ Fragkaki, A. G.; Angelis, Y. S.; Koupparis, M.; Tsantili-Kakoulidou, A.; Kokotos, G.; Georgakopoulos, C. (2009-02). "Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. Applied modifications in the steroidal structure". Steroids. 74 (2): 172–197. doi:10.1016/j.steroids.2008.10.016. ISSN 0039-128X. PMID 19028512. {{cite journal}}: Check date values in: |date= (help)
  27. ^ academic.oup.com https://academic.oup.com/crawlprevention/governor?content=%2fedrv%2farticle%2f25%2f2%2f276%2f2355261. Retrieved 2023-12-09. {{cite web}}: Missing or empty |title= (help)
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