Nandrolone Explained

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 (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin).[1] [2] [3] [4] Nandrolone esters are used in the treatment of anemias, cachexia (muscle wasting syndrome), osteoporosis, breast cancer, and for other indications. They are now used by oral administration or instead are given by injection into muscle or fat.[5]

Side effects of nandrolone esters include symptoms of masculinization like acne, increased hair growth, and voice changes. They are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).[6] Nandrolone has strong anabolic effects and weak androgenic effects, which give them a mild side effect profile and make them especially suitable for use in women and children.[7] There are metabolites of Nandrolone that act as long-lasting prodrugs in the body, such as 5α-Dihydronandrolone.

Nandrolone esters were first described and introduced for medical use in the late 1950s. They are among the most widely used anabolic steroid worldwide. In addition to their medical use, nandrolone esters are used to improve physique and performance, and are said to be the most widely used anabolic steroid for such purposes.[8] The drugs are controlled substances in many countries and so non-medical use is generally illicit.

Medical uses

Nandrolone esters are used clinically, although increasingly rarely, for people in catabolic states with major burns, cancer, and AIDS, and an ophthalmological formulation was available to support cornea healing.

The positive effects of nandrolone esters include muscle growth, appetite stimulation and increased red blood cell production, and bone density.[9] Clinical studies have shown them to be effective in treating anemia, osteoporosis, and breast cancer.

Nandrolone sulfate has been used in an eye drop formulation as an ophthalmic medication.

Non-medical uses

Nandrolone esters are used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.

Side effects

Side effects of nandrolone esters include masculinization among others. In women, nandrolone and nandrolone esters have been reported to produce increased libido, acne, facial and body hair growth, voice changes, and clitoral enlargement. However, the masculinizing effects of nandrolone and its esters are reported to be slighter than those of testosterone. Nandrolone has also been found to produce penile growth in prepubertal boys. Amenorrhea and menorrhagia have been reported as side effects of nandrolone cypionate.

Nandrolone theoretically may produce erectile dysfunction as a side effect, although there is no clinical evidence to support this notion at present. Side effects of high doses of nandrolone may include cardiovascular toxicity as well as hypogonadism and infertility. Nandrolone may not produce scalp hair loss, although this is also theoretical.

Pharmacology

Pharmacodynamics

Nandrolone is an agonist of the AR, the biological target of androgens like testosterone and . Unlike testosterone and certain other anabolic steroids, nandrolone is not potentiated in androgenic tissues like the scalp, skin, and prostate, hence deleterious effects in these tissues are lessened.[10] This is because nandrolone is metabolized by 5α-reductase to the much weaker AR ligand 5α-dihydronandrolone (DHN), which has both reduced affinity for the androgen receptor (AR) relative to nandrolone in vitro and weaker AR agonistic potency in vivo. The lack of alkylation on the 17α-carbon drastically reduces the hepatotoxic potential of nandrolone. Estrogen effects resulting from reaction with aromatase are also reduced due to lessened enzyme interaction,[11] but effects such as gynecomastia and reduced libido may still occur at sufficiently high doses.

In addition to its AR agonistic activity, unlike many other anabolic steroids, nandrolone is also a potent progestogen.[12] It binds to the progesterone receptor with approximately 22% of the affinity of progesterone. The progestogenic activity of nandrolone serves to augment its antigonadotropic effects, as antigonadotropic action is a known property of progestogens.[13] [14]

Anabolic and androgenic activity

Nandrolone has a very high ratio of anabolic to androgenic activity.[6] In fact, many nandrolone-like anabolic steroids and even nandrolone itself are said to have among the highest ratio of anabolic to androgenic effect of all anabolic steroids.[15] This is attributed to the fact that whereas testosterone is potentiated via conversion into dihydrotestosterone (DHT) in androgenic tissues, the opposite is true with nandrolone and similar anabolic steroids (i.e., other 19-nortestosterone derivatives). As such, nandrolone-like anabolic steroids, namely nandrolone esters, are the most frequently used anabolic steroids in clinical settings in which anabolic effects are desired; for instance, in the treatment of AIDS-associated cachexia, severe burns, and chronic obstructive pulmonary disease. However, anabolic steroids with a very high ratio of anabolic to androgenic action like nandrolone still have significant androgenic effects and can produce symptoms of masculinization like hirsutism and voice deepening in women and children with extended use.

Pharmacokinetics

The oral activity of nandrolone has been studied.[16] [17] [18] [19] [20] [21] With oral administration of nandrolone in rodents, it had about one-tenth of the potency of subcutaneous injection of nandrolone.[22] [23]

Nandrolone has very low affinity for human serum sex hormone-binding globulin (SHBG), about 5% of that of testosterone and 1% of that of DHT.[24] It is metabolized by the enzyme 5α-reductase, among others.[25] Nandrolone is less susceptible to metabolism by 5α-reductase and 17β-hydroxysteroid dehydrogenase than testosterone. This results in it being transformed less in so-called "androgenic" tissues like the skin, hair follicles, and prostate gland and in the kidneys, respectively. Metabolites of nandrolone include 5α-dihydronandrolone, 19-norandrosterone, and 19-noretiocholanolone, and these metabolites may be detected in urine.[26]

Single intramuscular injections of 100 mg nandrolone phenylpropionate or nandrolone decanoate have been found to produce an anabolic effect for 10 to 14 days and 20 to 25 days, respectively.[27] Conversely, unesterified nandrolone has been used by intramuscular injection once daily.

Chemistry

See also: List of androgens/anabolic steroids.

Nandrolone, also known as 19-nortestosterone (19-NT) or as estrenolone, as well as estra-4-en-17β-ol-3-one or 19-norandrost-4-en-17β-ol-3-one,[28] is a naturally occurring estrane (19-norandrostane) steroid and a derivative of testosterone (androst-4-en-17β-ol-3-one). It is specifically the C19 demethylated (nor) analogue of testosterone. Nandrolone is an endogenous intermediate in the production of estradiol from testosterone via aromatase in mammals including humans and is present in the body naturally in trace amounts.[29] It can be detected during pregnancy in women.[30] Nandrolone esters have an ester such as decanoate or phenylpropionate attached at the C17β position.

Derivatives

Esters

A variety of esters of nandrolone have been marketed and used medically. The most commonly used esters are nandrolone decanoate and to a lesser extent nandrolone phenylpropionate. Examples of other nandrolone esters that have been marketed and used medically include nandrolone cyclohexylpropionate, nandrolone cypionate, nandrolone hexyloxyphenylpropionate, nandrolone laurate, nandrolone sulfate, and nandrolone undecanoate.

Anabolic steroids

See also: List of androgens/anabolic steroids.

Nandrolone is the parent compound of a large group of anabolic steroids. Notable examples include the non-17α-alkylated trenbolone and the 17α-alkylated ethylestrenol (ethylnandrol) and metribolone (R-1881), as well as the 17α-alkylated designer steroids norboletone and tetrahydrogestrinone (THG). The following is list of derivatives of nandrolone that have been developed as anabolic steroids:

Non-17α-alkylated derivatives
17α-Alkylated derivatives

Progestins

Nandrolone, together with ethisterone (17α-ethynyltestosterone), is also the parent compound of a large group of progestins, the norethisterone (17α-ethynyl-19-nortestosterone) derivatives.[31] [32] This family is subdivided into two groups: the estranes and the gonanes. The estranes include norethisterone (norethindrone), norethisterone acetate, norethisterone enanthate, lynestrenol, etynodiol diacetate, and noretynodrel, while the gonanes include norgestrel, levonorgestrel, desogestrel, etonogestrel, gestodene, norgestimate, dienogest (actually a 17α-cyanomethyl-19-nortestosterone derivative), and norelgestromin.

Synthesis

The elaboration of a method for the reduction of aromatic rings to the corresponding dihydrobenzenes under controlled conditions by A. J. Birch opened a convenient route to compounds related to the putative 19-norprogesterone.

This reaction, now known as the Birch reduction,[33] is typified by the treatment of the monomethyl ether of estradiol (1) with a solution of lithium metal in liquid ammonia in the presence of alcohol as a proton source. Initial reaction constituents of 1,4-dimetalation of the most electron deficient positions of the aromatic ring–in the case of an estrogen, the 1 and 4-positions. Rxn of the intermediate with the proton source leads to a dihydrobenzene; a special virtue of this sequence in steroids is the fact that the double bind at 2 is in effect becomes an enol ether moiety. Treatment of this product (2) with weak acid, oxalic acid for e.g., leads to the hydrolysis of the enol ether, producing β,γ-unconjugated ketone 3. Hydrolysis under more strenuous conditions (mineral acids) results in migration/conjugation of the olefin to yield nandrolone (4).

Esters

Detection in body fluids

Nandrolone use is directly detectable in hair or indirectly detectable in urine by testing for the presence of 19-norandrosterone, a metabolite. The International Olympic Committee has set a limit of 2.0 μg/L of 19-norandrosterone in urine as the upper limit,[36] beyond which an athlete is suspected of doping. In the largest nandrolone study performed on 621 athletes at the 1998 Nagano Olympic Games, no athlete tested over 0.4 μg/L. 19-Norandrosterone was identified as a trace contaminant in commercial preparations of androstenedione, which until 2004 was available without a prescription as a dietary supplement in the U.S.[37] [38] [39] [40]

A number of nandrolone cases in athletics occurred in 1999, which included high-profile athletes such as Merlene Ottey, Dieter Baumann, and Linford Christie.[41] However, the following year the detection method for nandrolone at the time was proved to be faulty. Mark Richardson, a British Olympic relay runner who tested positive for the substance, gave a significant amount of urine samples in a controlled environment and delivered a positive test for the drug, demonstrating that false positives could occur, which led to an overhaul of his competitive ban.[42]

Heavy consumption of the essential amino acid lysine (as indicated in the treatment of cold sores) has allegedly shown false positives in some and was cited by American shotputter C. J. Hunter as the reason for his positive test, though in 2004 he admitted to a federal grand jury that he had injected nandrolone.[43] A possible cause of incorrect urine test results is the presence of metabolites from other anabolic steroids, though modern urinalysis can usually determine the exact anabolic steroid used by analyzing the ratio of the two remaining nandrolone metabolites. As a result of the numerous overturned verdicts, the testing procedure was reviewed by UK Sport. In October 2007, three-time Olympic gold medalist for track and field Marion Jones admitted to use of the drug, and was sentenced to six months in jail for lying to a federal grand jury in 2000.[44]

Mass spectrometry is also used to detect small amounts of nandrolone in urine samples.[45]

History

Nandrolone was first synthesized in 1950.[46] It was first introduced, as nandrolone phenylpropionate, in 1959, and then as nandrolone decanoate in 1962, followed by additional esters.[47]

Society and culture

Generic names

Nandrolone is the generic name of the drug and its,,, and .[48] [49] The formal generic names of nandrolone esters include nandrolone cyclohexylpropionate, nandrolone cyclotate, nandrolone decanoate, nandrolone laurate, nandrolone phenpropionate, and nandrolone phenylpropionate .

Doping in sports

Nandrolone was probably among the first anabolic steroids to be used as a doping agent in sports in the 1960s. It has been banned at the Olympics since 1974.[50] There are many known cases of doping in sports with nandrolone esters by professional athletes.

Research

Nandrolone esters have been studied in several indications. They were intensively studied for osteoporosis, and increased calcium uptake and decreased bone loss, but caused virilization in about half of the women who took them and were mostly abandoned for this use when better drugs like the bisphosphonates became available.[51] They have also been studied in clinical trials for chronic kidney failure, aplastic anemia, and as male contraceptives.[50]

Further reading

Notes and References

  1. Book: The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 2014. 978-1-4757-2085-3. Elks J, Ganellin CR . New York City. 660–. 1079003025.
  2. Book: Index Nominum 2000: International Drug Directory. January 2000. Taylor & Francis. 978-3-88763-075-1. 716–.
  3. Book: Llewellyn W . Anabolics. 2011. Molecular Nutrition Llc. 978-0-9828280-1-4. 402–412, 460–467, 193–194.
  4. Book: Sneader W . Drug Discovery: A History. 23 June 2005. John Wiley & Sons. 978-0-471-89979-2. 206–.
  5. Singh GK, Turner L, Desai R, Jimenez M, Handelsman DJ . Pharmacokinetic-pharmacodynamic study of subcutaneous injection of depot nandrolone decanoate using dried blood spots sampling coupled with ultrapressure liquid chromatography tandem mass spectrometry assays . The Journal of Clinical Endocrinology and Metabolism . 99 . 7 . 2592–8 . July 2014 . 24684468 . 10.1210/jc.2014-1243 . free .
  6. Kicman AT . Pharmacology of anabolic steroids . British Journal of Pharmacology . 154 . 3 . 502–21 . June 2008 . 18500378 . 2439524 . 10.1038/bjp.2008.165 .
  7. Book: Kochakian CD . Anabolic-Androgenic Steroids. 6 December 2012. Springer Science & Business Media. 978-3-642-66353-6. 401–.
  8. Book: Jameson JL, De Groot LJ . Endocrinology: Adult and Pediatric E-Book. 25 February 2015. Elsevier Health Sciences. 978-0-323-32195-2. 2388–.
  9. Book: https://www.ncbi.nlm.nih.gov/books/NBK278943/. Endotext. Handelsman DJ . 2013. De Groot LJ . 4.1.2 Pharmacologic Androgen Therapy. Androgen Physiology, Pharmacology and Abuse. MDText.com. 25905160 . Both testosterone and its non-aromatizable derivative nandrolone, produce increased bone density in men with glucocorticoid-induced osteoporosis with minimal short-term side-effects..... NCBI Bookshelf.
  10. Bergink EW, Janssen PS, Turpijn EW, van der Vies J . Comparison of the receptor binding properties of nandrolone and testosterone under in vitro and in vivo conditions . Journal of Steroid Biochemistry . 22 . 6 . 831–6 . June 1985 . 4021486 . 10.1016/0022-4731(85)90293-6 .
  11. Encyclopedia: Brueggemeier RW . Meyers RA . September 16, 2006 . Encyclopedia of Molecular Cell Biology and Molecular Medicine . . abstract . 10.1002/3527600906.mcb.200500066 . Sex Hormones (Male): Analogs and Antagonists . 978-3527600908 .
  12. Kuhl H . Pharmacology of estrogens and progestogens: influence of different routes of administration . Climacteric . 8 . 3–63 . August 2005 . Suppl 1 . 16112947 . 10.1080/13697130500148875 . 24616324 .
  13. Couzinet B, Young J, Brailly S, Chanson P, Thomas JL, Schaison G . The antigonadotropic activity of progestins (19-nortestosterone and 19-norprogesterone derivatives) is not mediated through the androgen receptor . The Journal of Clinical Endocrinology and Metabolism . 81 . 12 . 4218–23 . December 1996 . 8954018 . 10.1210/jcem.81.12.8954018 . free .
  14. Mauvais-Jarvis, P. "Progesterone and progestins: a general overview." (1983): 1-16.
  15. de Souza GL, Hallak J . Anabolic steroids and male infertility: a comprehensive review . BJU International . 108 . 11 . 1860–5 . December 2011 . 21682835 . 10.1111/j.1464-410X.2011.10131.x . 29035729 . free .
  16. Camerino B, Sciaky R . Structure and effects of anabolic steroids . Pharmacology & Therapeutics B . 1 . 2 . 233–75 . 1975 . 817322 . 10.1016/0306-039X(75)90007-0 .
  17. Holtkamp DE, Heming AE, Mansor LF . Comparison of Oral and Subcutaneous Administration in the Anabolic and Androgenic Effectiveness of 19-Nortestosterone and Testosterone . The Journal of Clinical Endocrinology & Metabolism . 15 . 7 . 1955 . 848 . 0021-972X . 10.1210/jcem-15-7-834 . free .
  18. Furman RH, Howard RP, Smith CW, Norcia LN . Comparison of the effects of oral methyltestosterone, 19-nortestosterone, and 17-methyl-19-nortestosterone on serum lipids and lipoproteins . January 1956 . Journal of Laboratory and Clinical Medicine . 48 . 5 . 808–809 .
  19. Furman RH, Howard RP, Norcia LN, Keaty EC . The influence of androgens, estrogens and related steroids on serum lipids and lipoproteins . The American Journal of Medicine . 24 . 1 . 80–97 . January 1958 . 13498038 . 10.1016/0002-9343(58)90364-4 .
  20. McEvoy JD, McVeigh CE, McCaughey WJ . Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability . The Analyst . 123 . 12 . 2475–8 . December 1998 . 10435281 . 10.1039/a804919j .
  21. Arnold A, Potts GO . Oral anabolic and androgenic effects of 19-nortestosterone and 17α-methyl-19-nortestosterone . Federation Proceedings . January 1964 . 23 . 2 . 412 .
  22. Baker WH, Henneman PH, Baggett B, Engel LL, Tibbetts D, Brown M . Metabolic effect of 19-nortestosterone . Journal of Clinical Endocrinology & Metabolism . January 1955 . 15 . 7 . 848–849 . 0021-972X . 10.1210/jcem-15-7-834 . free .
  23. Book: Camerino B, Sala G . Anabolic Steroids . Fortschritte der Arzneimittelforschung. Progress in Drug Research. Progres des Recherches Pharmaceutiques . Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques . 1960. 2. 71–134. 10.1007/978-3-0348-7038-2_2. 14448579. 978-3-0348-7040-5 .
  24. Saartok T, Dahlberg E, Gustafsson JA . Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin . Endocrinology . 114 . 6 . 2100–6 . June 1984 . 6539197 . 10.1210/endo-114-6-2100 .
  25. Bergink EW, Geelen JA, Turpijn EW . Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions . Acta Endocrinologica. Supplementum . 271 . 3_Suppla . 31–7 . 1985 . 3865479 . 10.1530/acta.0.109S0031 .
  26. Book: Mottram DR . Drugs in Sport. 12 November 2010. Routledge. 978-1-135-25825-2. 63–.
  27. Book: Dorfman RI . Steroidal Activity in Experimental Animals and Man. 5 December 2016. Elsevier Science. 978-1-4832-7300-6. 68–.
  28. Book: Schnitzer R . Experimental Chemotherapy. 1 January 1967. Elsevier Science. 978-0-323-14611-1. 165–.
  29. Bricout V, Wright F . Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances? . European Journal of Applied Physiology . 92 . 1–2 . 1–12 . June 2004 . 15042372 . 10.1007/s00421-004-1051-3 . 6472015 .
  30. Lippi G, Franchini M, Banfi G . Biochemistry and physiology of anabolic androgenic steroids doping . Mini Reviews in Medicinal Chemistry . 11 . 5 . 362–73 . May 2011 . 21443514 . 10.2174/138955711795445952 . 3862299 .
  31. Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH . Classification and pharmacology of progestins . Maturitas . 46 . S7–S16 . December 2003 . Suppl 1 . 14670641 . 10.1016/j.maturitas.2003.09.014 .
  32. Book: Meikle AW . Endocrine Replacement Therapy in Clinical Practice. 24 April 2003. Springer Science & Business Media. 978-1-59259-375-0. 489–. Estranes. Estrane and gonane progestogens are derived from 19-nortestosterone, the progestogenic parent compound used in oral contraceptives in the United States. Estranes are characterized by the presence of an ethinyl group at position 17 and by the absence of a methyl group between the A and B rings (see Fig. 10). The estrane progestogens that are related structurally to norethindrone (norethynodrel, lynestrenol, norethindrone acetate, ethynodiol diacetate) are converted to this parent compound. Norethindrone is the second most commonly used progestogen in the United States for HRT. Gonanes. The gonanes share the structural modifications found in the estranes and also possess an ethinyl group at position 13 and a keto group at position 3 (see Fig. 11). Norgestrel was synthesized in 1963 and is a racemic mixture of dextro and levorotatory forms. The levorotatory form, levonorgestrel, provides the biologic activity. Third-generation gonanes (desogestrel, gestodene, and norgestimate) have been developed to reduce unwanted side effects of progestogens, [...].
  33. 10.1039/QR9500400069. The reduction of organic compounds by metal-ammonia solutions. Quarterly Reviews, Chemical Society. 4. 69. 1950. Birch AJ .
  34. DeWytt ED, Overbeek O, Overbeek GA . US . 2998423 . 1961 . . .
  35. CH. 206119 . 1939 . .
  36. News: Clarification about Nandrolone Testing . 2005-05-30 . World Anti-Doping Agency . 2012-01-31 . dead . https://archive.today/20120915060715/http://www.wada-ama.org/en/News-Center/Articles/Clarification-about-Nandrolone-Testing1/ . 2012-09-15 .
  37. Bresson M, Cirimele V, Villain M, Kintz P . Doping control for metandienone using hair analyzed by gas chromatography-tandem mass spectrometry . Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences . 836 . 1–2 . 124–8 . May 2006 . 16597518 . 10.1016/j.jchromb.2006.03.040 .
  38. Ueki M, Ikekita A, Takao Y . [Nandrolone metabolite in urine of Nagano Olympic athlete] . Jap. J. For. Tox. . 18 . 198–199 . 2000 . ja .
  39. Catlin DH, Leder BZ, Ahrens B, Starcevic B, Hatton CK, Green GA, Finkelstein JS . Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite . JAMA . 284 . 20 . 2618–21 . 2000 . 11086369 . 10.1001/jama.284.20.2618 . free .
  40. Book: Baselt RC . Disposition of Toxic Drugs and Chemicals in Man . 8th . Biomedical Publications . Foster City, CA . 2008 . 978-0-9626523-7-0 . 1078–1080 . 2010-08-19 . 2020-12-04 . https://web.archive.org/web/20201204114016/http://www.biomedicalpublications.com/ . dead .
  41. Web site: The Drugs Issue: Baumann to fight all the way . Baron P . The Telegraph . 19 September 2000 . 2010-11-13 . subscription .
  42. News: Athletics: Mark Richardson explains how he felt at his disciplinary hearing . Richardson M . 2004-02-19 . . 2010-11-13 .
  43. Web site: Track Star Marion Jones to Admit Steroid Use . National Public Radio . 2007-10-05 . 2009-11-09 .
  44. UK Sport Anti-doping Directorate . January 2000 . Nandrolone Review . https://web.archive.org/web/20050404200642/http://www.uksport.gov.uk/images/uploaded/nandrevv2.pdf . 2005-04-04 . . 2013-02-02 .
  45. Buiarelli F, Giannetti L, Jasionowska R, Cruciani C, Neri B . Rapid Communications in Mass Spectrometry . Determination of nandrolone metabolites in human urine: comparison between liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry . 24 . 13 . 1881–1894 . July 2010 . 10.1002/rcm.4583. 20533318 . 2010RCMS...24.1881B . free .
  46. Birch AJ . 80. Hydroaromatic steroid hormones. Part I. 10-Nortestosterone. Journal of the Chemical Society (Resumed). 1950. 367. 0368-1769. 10.1039/jr9500000367.
  47. Book: Consolidated List of Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments. 1983. United Nations Publications. 978-92-1-130230-1. 154–.
  48. Book: Morton IK, Hall JM . Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012. Springer Science & Business Media. 978-94-011-4439-1.
  49. Web site: Nandrolone.
  50. Book: Hemmersbach P, Große J . Thieme D, Hemmersbach P . Doping in sports. 2009. Springer. Berlin. 978-3-540-79088-4. 127–154. Nandrolone: A Multi-Faceted Doping Agent.
  51. Pan MM, Kovac JR . Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness . Translational Andrology and Urology . 5 . 2 . 213–9 . April 2016 . 27141449 . 4837307 . 10.21037/tau.2016.03.03 . free .