Nandrolone: Difference between revisions

{{Short description|Androgenic Anabolic steroid}}

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 443236429

| image = Nandrolone.svg

| width = 225

| image2 = Nandrolone molecule ball.png

| width2 = 225

<!--Clinical data-->

| pronounce = {{IPAc-en|ˈ|n|æ|n|d|r|ə|l|oʊ|n}}<ref>{{cite web | url=http://dictionary.cambridge.org/dictionary/british/nandrolone | title=Nandrolone Meaning in the Cambridge English Dictionary}}</ref>

| tradename = • Deca-Durabolin (as {{abbrlink|ND|nandrolone decanoate}})<br />• Durabolin (as {{abbrlink|NPP|nandrolone phenylpropionate}})<br />• Many others (see [[List of androgen esters#Nandrolone esters|here]])

| MedlinePlus =

| licence_EU =

| licence_US =

| pregnancy_AU = D

| pregnancy_category =

| legal_BR = C5

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>

| legal_CA = Schedule IV

| legal_UK = Class C

| legal_US = Schedule III

| legal_status =

| routes_of_administration = • [[Intramuscular injection|{{Abbr|IM|Intramuscular}} injection]] ([[nandrolone ester|ester]]s)<br />• [[Subcutaneous injection|{{Abbr|SC|Subcutaneous}} injection]] ([[nandrolone ester|ester]]s)<br />• [[Eye drop]]s ({{abbrlink|NS|nandrolone sulfate}})

| class = [[Androgen]]; [[Anabolic steroid]]; [[Progestogen]]

<!--Pharmacokinetic data-->

| bioavailability = • [[Oral administration|Oral]]: <3% (pigs)<ref name="McEvoyMcVeigh1998">{{cite journal | vauthors = McEvoy JD, McVeigh CE, McCaughey WJ | title = Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability | journal = The Analyst | volume = 123 | issue = 12 | pages = 2475–8 | date = December 1998 | pmid = 10435281 | doi = 10.1039/a804919j }}</ref><br />• [[Intramuscular injection|Intramuscular]]: high<ref name="Becker2001">{{cite book| vauthors = Becker KL |title=Principles and Practice of Endocrinology and Metabolism|url=https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=1185–}}</ref>

| protein_bound =

| metabolism = [[Liver]] ([[redox|reduction]])<ref name="Label-NZ" /><ref name="Thomas2012">{{cite book| vauthors = Thomas JA |title=Drugs, Athletes, and Physical Performance|url=https://books.google.com/books?id=9u0pBgAAQBAJ&pg=PA27|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4684-5499-4|pages=27–29}}</ref>

| metabolites = • [[5α-Dihydronandrolone]]<ref name="Label-NZ" /><ref name="Llewellyn2011" /><br />• [[19-Norandrosterone]]<ref name="Label-NZ" /><br />• [[19-Noretiocholanolone]]<ref name="Label-NZ" /><br />• [[Conjugation (biochemistry)|Conjugate]]s<ref name="Thomas2012" />

| elimination_half-life = • Nandrolone: <4.3 hours<ref name="Label-NZ">{{cite web | title = Deca-Durabolin | work = Schering-Plough | url = http://www.medsafe.govt.nz/profs/Datasheet/d/Decadurabolininj.pdf | archive-url = https://web.archive.org/web/20101218225941/http://www.medsafe.govt.nz/profs/Datasheet/d/Decadurabolininj.pdf | archive-date = 18 December 2010 }}</ref><br />• {{abbrlink|ND|Nandrolone decanoate}} ({{abbrlink|IM|Intramuscular injection}}): 6–12 days<ref name="Label-NZ" /><ref name="Llewellyn2011" /><ref name="pmid9103484"/><br />• {{abbrlink|NPP|Nandrolone phenylpropionate}}: 2.7 days<ref name="pmid9103484">{{cite journal | vauthors = Minto CF, Howe C, Wishart S, Conway AJ, Handelsman DJ | title = Pharmacokinetics and pharmacodynamics of nandrolone esters in oil vehicle: effects of ester, injection site and injection volume | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 281 | issue = 1 | pages = 93–102 | date = April 1997 | pmid = 9103484 }}</ref>

| duration_of_action = • {{abbr|ND|Nandrolone decanoate}} ({{abbr|IM|Intramuscular injection}}): 2–3 weeks<ref name="Llewellyn2011" /><ref name="Label-AU">{{cite web | title = Deca-Durabolin | url = https://gp2u.com.au/static/pdf/D/DECA-DURABOLIN-PI.pdf | work = Merck Sharp & Dohme (Australia) }}</ref><br />• {{abbr|NPP|Nandrolone phenylpropionate}} ({{abbr|IM|Intramuscular injection}}): 5–7 days<ref name="Llewellyn2011" /><ref name="pmid9103484" />

| excretion = [[Urine]]<ref name="Label-NZ" />

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 434-22-0

| ATC_prefix = A14

| ATC_suffix = AB01

| ATC_supplemental = {{ATC|S01|XA11}}

| DrugBank_Ref =

| DrugBank = DB13169

| PubChem = 9904

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9520

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 7466

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 757

| IUPHAR_ligand = 6949

| synonyms = • 19-Nortestosterone<ref name="Elks2014" /><ref name="MortonHall2012" /><br />• 10-Nortestosterone<br />• Estr-4-en-17β-ol-3-one<br />• Estrenolone<br />• Oestrenolone<br />• 19-Norandrost-4-en-17β-ol-3-one<br />• Norandrostenolone<ref name="Elks2014" /><br />• Nortestrionate<ref name="Elks2014" /><br />• Nortestonate<ref name="Elks2014" /><br />• Norandroone<br />• SG-4341<ref name="Elks2014" /><ref name="MortonHall2012" />

<!--Chemical data-->

| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1''H''-cyclopenta[''a'']phenanthren-3-one

| C=18 | H=26 | O=2

| SMILES = O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4

<!-- Definition and medical uses -->

'''Nandrolone''', also known as '''19-nortestosterone''', is an [[endogenous]] [[androgen]]. It is also an [[anabolic steroid]] (AAS) which is medically used in the form of [[ester]]s such as [[nandrolone decanoate]] (brand name '''Deca-Durabolin''') and [[nandrolone phenylpropionate]] (brand name '''Durabolin''').<ref name="Elks2014">{{cite book|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|publisher=Springer|year=2014|isbn=978-1-4757-2085-3| veditors = Elks J, Ganellin CR |location=New York City|pages=660–|oclc=1079003025<!--1 to 1 oclc to isbn at time of edit-->}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA716|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=716–}}</ref><ref name="Llewellyn2011">{{cite book| vauthors = Llewellyn W |title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT402|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=402–412, 460–467, 193–194}}</ref><ref name="Sneader2005">{{cite book| vauthors = Sneader W |title=Drug Discovery: A History|url=https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA206|date=23 June 2005|publisher=John Wiley & Sons|isbn=978-0-471-89979-2|pages=206–}}</ref> [[Nandrolone ester]]s are used in the treatment of [[anemia]]s, [[cachexia]] ([[Skeletal muscle|muscle]] wasting syndrome), [[osteoporosis]], [[breast cancer]], and for other indications.<ref name="Llewellyn2011" /> They are now used by [[oral administration]] or instead are given by [[intramuscular injection|injection into muscle]] or [[subcutaneous injection|fat]].<ref name="Llewellyn2011" /><ref name="Sneader2005" /><ref name="SinghTurner2014">{{cite journal | vauthors = Singh GK, Turner L, Desai R, Jimenez M, Handelsman DJ | title = Pharmacokinetic-pharmacodynamic study of subcutaneous injection of depot nandrolone decanoate using dried blood spots sampling coupled with ultrapressure liquid chromatography tandem mass spectrometry assays | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 99 | issue = 7 | pages = 2592–8 | date = July 2014 | pmid = 24684468 | doi = 10.1210/jc.2014-1243 | doi-access = free }}</ref>

<!-- Side effects and mechanism of action -->

[[Side effect]]s of nandrolone esters include [[symptom]]s of [[virilization|masculinization]] like [[acne]], [[hirsutism|increased hair growth]], and [[voice deepening|voice changes]].<ref name="Llewellyn2011" /> They are [[synthetic compound|synthetic]] androgens and anabolic steroids and hence are [[agonist]]s of the [[androgen receptor]] (AR), the [[biological target]] of androgens like [[testosterone]] and [[dihydrotestosterone]] (DHT).<ref name="Llewellyn2011" /><ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–21 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> Nandrolone has strong [[anabolic]] effects and weak [[androgen]]ic effects, which give them a mild side effect profile and make them especially suitable for use in women and children.<ref name="Llewellyn2011" /><ref name="pmid18500378" /><ref name="Kochakian2012">{{cite book| vauthors = Kochakian CD |title=Anabolic-Androgenic Steroids|url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA401|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6|pages=401–}}</ref> There are metabolites of Nandrolone that act as long-lasting [[prodrug]]s in the body,<ref name="Llewellyn2011" /> such as [[5α-Dihydronandrolone]].

<!-- History, society, and culture -->

Nandrolone esters were first described and introduced for medical use in the late 1950s.<ref name="Llewellyn2011" /> They are among the most widely used anabolic steroid worldwide.<ref name="Llewellyn2011" /> In addition to their medical use, nandrolone esters are used to [[performance-enhancing substance|improve physique and performance]], and are said to be the most widely used anabolic steroid for such purposes.<ref name="Llewellyn2011" /><ref name="JamesonGroot2015">{{cite book| vauthors = Jameson JL, De Groot LJ |title=Endocrinology: Adult and Pediatric E-Book|url=https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2388|date=25 February 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-32195-2|pages=2388–}}</ref> The drugs are [[controlled substance]]s in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" />

{{TOC limit|3}}

==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.<ref name=HemmersbachChapter2009/>{{rp|134}}

The positive effects of nandrolone esters include muscle growth, appetite stimulation and increased [[red blood cell]] production,{{medcn|date=July 2015}} and [[bone density]].<ref>{{cite book|chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK278943/|title=Endotext| vauthors = Handelsman DJ |year=2013| veditors = De Groot LJ |at=4.1.2 Pharmacologic Androgen Therapy|chapter=Androgen Physiology, Pharmacology and Abuse|publisher=MDText.com|pmid=25905160 |quote=Both testosterone and its non-aromatizable derivative nandrolone, produce increased bone density in men with glucocorticoid-induced osteoporosis with minimal short-term side-effects....|via=NCBI Bookshelf}}</ref> 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 drug administration|ophthalmic]] medication.<ref name="Elks2014" /><ref name="IndexNominum2000" />

==Non-medical uses==

Nandrolone esters are used for [[performance-enhancing drug|physique- and performance-enhancing purpose]]s by [[competition|competitive]] [[athlete]]s, [[bodybuilder]]s, and [[powerlifter]]s.<ref name="Llewellyn2011" />

==Side effects==

{{See also|Anabolic steroid#Adverse effects}}

[[Side effect]]s of nandrolone esters include [[virilization|masculinization]] among others.<ref name="Llewellyn2011" /> In women, nandrolone and [[nandrolone ester]]s have been reported to produce increased [[libido]], [[acne]], [[facial hair|facial]] and [[body hair]] [[hair growth|growth]], [[voice deepening|voice changes]], and [[clitoral enlargement]].<ref name="CamerinoSala1960" /> However, the masculinizing effects of nandrolone and its esters are reported to be slighter than those of [[testosterone (medication)|testosterone]].<ref name="CamerinoSala1960" /> Nandrolone has also been found to produce [[penile growth]] in prepubertal boys.<ref name="CamerinoSala1960" /> [[Amenorrhea]] and [[menorrhagia]] have been reported as side effects of [[nandrolone cypionate]].<ref name="CamerinoSala1960" />

Nandrolone theoretically may produce [[erectile dysfunction]] as a side effect, although there is no clinical evidence to support this notion at present.<ref name="pmid27141449" /> Side effects of high doses of nandrolone may include [[cardiovascular]] [[toxicity]] as well as [[hypogonadism]] and [[infertility]].{{Citation needed|date=December 2017}} Nandrolone may not produce [[scalp hair loss]], although this is also theoretical.<ref name="pmid27141449" />

==Pharmacology==

===Pharmacodynamics===

{{Relative androgenic to anabolic activity in animals}}

Nandrolone is an [[agonist]] of the AR, the [[biological target]] of [[androgen]]s like [[testosterone]] and {{abbrlink|DHT|dihydrotestosterone}}. 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.<ref name="pmid4021486">{{cite journal | vauthors = Bergink EW, Janssen PS, Turpijn EW, van der Vies J | title = Comparison of the receptor binding properties of nandrolone and testosterone under in vitro and in vivo conditions | journal = Journal of Steroid Biochemistry | volume = 22 | issue = 6 | pages = 831–6 | date = June 1985 | pmid = 4021486 | doi = 10.1016/0022-4731(85)90293-6 }}</ref> This is because nandrolone is metabolized by [[5α-reductase]] to the much weaker AR ligand [[5α-dihydronandrolone]] (DHN), which has both reduced [[affinity (pharmacology)|affinity]] for the [[androgen receptor]] (AR) relative to nandrolone ''[[in vitro]]'' and weaker AR agonistic [[potency (pharmacology)|potency]] ''[[in vivo]]''.<ref name="pmid4021486" /> The lack of alkylation on the 17α-carbon drastically reduces the [[hepatotoxicity|hepatotoxic]] potential of nandrolone.{{Medcn|date=July 2015}} [[Estrogen (medication)|Estrogen]] effects resulting from reaction with [[aromatase]] are also reduced due to lessened enzyme interaction,<ref name=brueggemeier2006>{{cite encyclopedia | vauthors = Brueggemeier RW | veditors = Meyers RA | date = September 16, 2006 | encyclopedia = Encyclopedia of Molecular Cell Biology and Molecular Medicine | publisher = [[John Wiley & Sons]] | type = abstract | doi = 10.1002/3527600906.mcb.200500066 | chapter = Sex Hormones (Male): Analogs and Antagonists | isbn = 978-3527600908 }}</ref> but effects such as [[gynecomastia]] and reduced [[libido]] may still occur at sufficiently high doses.{{Citation needed|date=December 2017}}

In addition to its AR agonistic activity, unlike many other anabolic steroids, nandrolone is also a potent [[progestogen]].<ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | pages = 3–63 | date = August 2005 | issue = Suppl 1 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 }}</ref> It binds to the [[progesterone receptor]] with approximately 22% of the affinity of [[progesterone]].<ref name="pmid16112947" /> The progestogenic activity of nandrolone serves to augment its [[antigonadotropic]] effects,<ref name="pmid21682835" /><ref name="Llewellyn2011" /> as antigonadotropic action is a known property of progestogens.<ref name="pmid8954018">{{cite journal | vauthors = Couzinet B, Young J, Brailly S, Chanson P, Thomas JL, Schaison G | title = The antigonadotropic activity of progestins (19-nortestosterone and 19-norprogesterone derivatives) is not mediated through the androgen receptor | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 81 | issue = 12 | pages = 4218–23 | date = December 1996 | pmid = 8954018 | doi = 10.1210/jcem.81.12.8954018 | doi-access = free }}</ref><ref name="Mauvais-Jarvis1983">Mauvais-Jarvis, P. "Progesterone and progestins: a general overview." (1983): 1-16.</ref>

{{Relative affinities of nandrolone and related steroids}}

====Anabolic and androgenic activity====

Nandrolone has a very high ratio of anabolic to androgenic activity.<ref name="pmid18500378"/> 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.<ref name="pmid21682835">{{cite journal | vauthors = de Souza GL, Hallak J | title = Anabolic steroids and male infertility: a comprehensive review | journal = BJU International | volume = 108 | issue = 11 | pages = 1860–5 | date = December 2011 | pmid = 21682835 | doi = 10.1111/j.1464-410X.2011.10131.x | s2cid = 29035729 | doi-access = free }}</ref> 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).<ref name="pmid18500378" /> 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 [[HIV/AIDS|AIDS]]-associated [[cachexia]], severe [[burn]]s, and [[chronic obstructive pulmonary disease]].<ref name="pmid21682835" /> 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 [[virilization|masculinization]] like [[hirsutism]] and [[voice change|voice deepening]] in women and children with extended use.<ref name="pmid18500378" />

{{Relative affinities of nandrolone and related steroids at the androgen receptor}}

===Pharmacokinetics===

The [[oral administration|oral]] activity of nandrolone has been studied.<ref name="CamerinoSciaky1975">{{cite journal | vauthors = Camerino B, Sciaky R | title = Structure and effects of anabolic steroids | journal = Pharmacology & Therapeutics B | volume = 1 | issue = 2 | pages = 233–75 | year = 1975 | pmid = 817322 | doi = 10.1016/0306-039X(75)90007-0 }}</ref><ref name="HoltkampHeming1955">{{cite journal | vauthors = Holtkamp DE, Heming AE, Mansor LF | title = Comparison of Oral and Subcutaneous Administration in the Anabolic and Androgenic Effectiveness of 19-Nortestosterone and Testosterone | journal = The Journal of Clinical Endocrinology & Metabolism | volume = 15 | issue = 7 | year = 1955 | pages = 848 | issn = 0021-972X | doi = 10.1210/jcem-15-7-834 | doi-access = free }}</ref><ref name="FurmanHoward1956">{{cite journal | vauthors = Furman RH, Howard RP, Smith CW, Norcia LN | title = Comparison of the effects of oral methyltestosterone, 19-nortestosterone, and 17-methyl-19-nortestosterone on serum lipids and lipoproteins | date = January 1956 | journal = Journal of Laboratory and Clinical Medicine | volume = 48 | issue = 5 | pages = 808–809 | url = https://scholar.google.com/scholar?cluster=2443238990532613043}}</ref><ref name="FurmanHoward1958">{{cite journal | vauthors = Furman RH, Howard RP, Norcia LN, Keaty EC | title = The influence of androgens, estrogens and related steroids on serum lipids and lipoproteins | journal = The American Journal of Medicine | volume = 24 | issue = 1 | pages = 80–97 | date = January 1958 | pmid = 13498038 | doi = 10.1016/0002-9343(58)90364-4 }}</ref><ref name="McEvoyMcVeigh1998">{{cite journal | vauthors = McEvoy JD, McVeigh CE, McCaughey WJ | title = Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability | journal = The Analyst | volume = 123 | issue = 12 | pages = 2475–8 | date = December 1998 | pmid = 10435281 | doi = 10.1039/a804919j }}</ref><ref name="ArnoldPotts1964">{{cite journal | vauthors = Arnold A, Potts GO | title = Oral anabolic and androgenic effects of 19-nortestosterone and 17α-methyl-19-nortestosterone | journal = Federation Proceedings | date = January 1964 | volume = 23 | issue = 2 | page = 412 | url = https://scholar.google.com/scholar?cluster=1176981003930267913}}</ref> With oral administration of nandrolone in rodents, it had about one-tenth of the [[potency (pharmacology)|potency]] of [[subcutaneous injection]] of nandrolone.<ref name="CamerinoSciaky1975" /><ref name="BakerHenneman1955">{{cite journal | vauthors = Baker WH, Henneman PH, Baggett B, Engel LL, Tibbetts D, Brown M | title = Metabolic effect of 19-nortestosterone | journal = Journal of Clinical Endocrinology & Metabolism | date = January 1955 | volume = 15 | issue = 7 | pages = 848–849 | issn = 0021-972X | doi = 10.1210/jcem-15-7-834 | doi-access = free }}</ref><ref name="CamerinoSala1960">{{cite book | vauthors = Camerino B, Sala G |chapter=Anabolic Steroids |journal=Fortschritte der Arzneimittelforschung. Progress in Drug Research. Progres des Recherches Pharmaceutiques |title=Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques |year=1960|volume=2|pages=71–134|doi=10.1007/978-3-0348-7038-2_2|pmid=14448579|isbn=978-3-0348-7040-5 }}</ref>

Nandrolone has very low [[affinity (pharmacology)|affinity]] for human serum [[sex hormone-binding globulin]] (SHBG), about 5% of that of testosterone and 1% of that of DHT.<ref name="pmid6539197">{{cite journal | vauthors = Saartok T, Dahlberg E, Gustafsson JA | title = 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 | journal = Endocrinology | volume = 114 | issue = 6 | pages = 2100–6 | date = June 1984 | pmid = 6539197 | doi = 10.1210/endo-114-6-2100 }}</ref> It is [[metabolism|metabolized]] by the [[enzyme]] [[5α-reductase]], among others.<ref name="pmid3865479">{{cite journal | vauthors = Bergink EW, Geelen JA, Turpijn EW | title = Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions | journal = Acta Endocrinologica. Supplementum | volume = 271 | issue = 3_Suppla | pages = 31–7 | date = 1985 | pmid = 3865479 | doi = 10.1530/acta.0.109S0031 }}</ref>{{Additional citation needed|date=March 2018}} Nandrolone is less susceptible to metabolism by 5α-reductase and [[17β-hydroxysteroid dehydrogenase]] than [[testosterone (medication)|testosterone]].<ref name="pmid3865479" /> This results in it being [[biotransformation|transformed]] less in so-called "androgenic" [[tissue (biology)|tissue]]s like the [[skin]], [[hair follicle]]s, and [[prostate gland]] and in the [[kidney]]s, respectively.<ref name="pmid3865479" /> [[Metabolite]]s of nandrolone include [[5α-dihydronandrolone]], [[19-norandrosterone]], and [[19-noretiocholanolone]], and these metabolites may be detected in [[urine]].<ref name="Mottram2010">{{cite book| vauthors = Mottram DR |title=Drugs in Sport|url=https://books.google.com/books?id=kmyNAgAAQBAJ&pg=PA63|date=12 November 2010|publisher=Routledge|isbn=978-1-135-25825-2|pages=63–}}</ref>

Single [[intramuscular injection]]s of 100&nbsp;mg [[nandrolone phenylpropionate]] or [[nandrolone decanoate]] have been found to produce an anabolic effect for 10 to 14&nbsp;days and 20 to 25&nbsp;days, respectively.<ref name="Dorfman2016">{{cite book | vauthors = Dorfman RI |title=Steroidal Activity in Experimental Animals and Man|url=https://books.google.com/books?id=uizgBAAAQBAJ&pg=PA68|date=5 December 2016|publisher=Elsevier Science|isbn=978-1-4832-7300-6|pages=68–}}</ref> Conversely, unesterified nandrolone has been used by intramuscular injection once daily.<ref name="CamerinoSala1960" /><ref name="BakerHenneman1955" />

{{Hormone levels with nandrolone esters by intramuscular injection}}

==Chemistry==

[[File:19-nortestosterones.svg|thumb|right|250px|Nandrolone, with the differences from testosterone highlighted in red. The [[methyl group]] in testosterone at the C19 position has been removed, and the C17β position is where esters are attached to nandrolone.]]

{{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,<ref name="Schnitzer1967">{{cite book| vauthors = Schnitzer R |title=Experimental Chemotherapy|url=https://books.google.com/books?id=elAJWRnKqDEC&pg=PA165|date=1 January 1967|publisher=Elsevier Science|isbn=978-0-323-14611-1|pages=165–}}</ref> is a [[natural compound|naturally occurring]] [[estrane]] (19-norandrostane) [[steroid]] and a [[chemical derivative|derivative]] of [[testosterone]] (androst-4-en-17β-ol-3-one).<ref name="Elks2014" /><ref name="IndexNominum2000" /> It is specifically the C19 [[demethylation|demethyl]]ated ([[nor-|nor]]) [[structural analogue|analogue]] of testosterone.<ref name="Elks2014" /><ref name="IndexNominum2000" /> Nandrolone is an [[endogenous]] [[metabolic intermediate|intermediate]] in the [[biosynthesis|production]] of [[estradiol]] from [[testosterone]] via [[aromatase]] in [[mammal]]s including humans and is present in the body naturally in trace amounts.<ref name="pmid15042372">{{cite journal | vauthors = Bricout V, Wright F | title = Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances? | journal = European Journal of Applied Physiology | volume = 92 | issue = 1–2 | pages = 1–12 | date = June 2004 | pmid = 15042372 | doi = 10.1007/s00421-004-1051-3 | s2cid = 6472015 }}</ref> It can be detected during [[pregnancy]] in women.<ref name="pmid21443514">{{cite journal | vauthors = Lippi G, Franchini M, Banfi G | title = Biochemistry and physiology of anabolic androgenic steroids doping | journal = Mini Reviews in Medicinal Chemistry | volume = 11 | issue = 5 | pages = 362–73 | date = May 2011 | pmid = 21443514 | doi = 10.2174/138955711795445952 | s2cid = 3862299 }}</ref> Nandrolone esters have an [[ester]] such as [[decanoate]] or [[phenylpropionate]] attached at the C17β position.<ref name="Elks2014" /><ref name="IndexNominum2000" />

===Derivatives===

====Esters====

{{See also|List of androgen esters#Nandrolone esters}}

A variety of esters of nandrolone have been marketed and used medically.<ref name="Elks2014" /><ref name="IndexNominum2000" /> 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]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />

====Anabolic steroids====

{{See also|List of androgens/anabolic steroids|List of androgen esters#Esters of synthetic 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 AAS|17α-alkylated]] [[ethylestrenol]] (ethylnandrol) and [[metribolone]] (R-1881), as well as the 17α-alkylated [[designer steroid]]s [[norboletone]] and [[tetrahydrogestrinone]] (THG). The following is list of derivatives of nandrolone that have been developed as anabolic steroids:<ref name="Llewellyn2011" />

{{Col-begin}}

{{Col-break}}

; Non-17α-alkylated derivatives

* Marketed

** [[Bolandiol]] (19-nor-4-androstenediol)

** [[Norclostebol]] (4-chloro-19-NT)

** [[Oxabolone]] (4-hydroxy-19-NT)

** [[Trenbolone]] (δ^9,11-19-NT)

* Never marketed

** [[7α-Methyl-19-nor-4-androstenedione]] (MENT dione, trestione)

** [[11β-Methyl-19-nortestosterone]] (11β-MNT; 11β-methyl-19-NT)

** [[19-Nor-5-androstenediol]]

** [[19-Nor-5-androstenedione]]

** [[Bolandione]] (19-nor-4-androstenedione)

** [[Dienedione]] (δ⁹-19-nor-4-androstenedione)

** [[Dienolone]] (δ⁹-19-NT)

** [[Dimethandrolone]] (7α,11β-dimethyl-19-NT)

** [[Methoxydienone]] (18-methyl-δ^2,5(10)-{{abbr|19-NEA|19-norepiandrosterone}} 3β-methyl ether)

** [[Trestolone]] (MENT; 7α-methyl-19-NT)

{{Col-break}}

; [[17α-Alkylated anabolic steroid|17α-Alkylated]] derivatives

* Marketed

** [[Ethylestrenol]] (ethylnandrol; 3-deketo-17α-ethyl-19-NT)

** [[Mibolerone]] (7α,17α-dimethyl-19-NT)

** [[Norethandrolone]] (17α-ethyl-19-NT)

** [[Normethandrone]] (methylestrenolone; 17α-methyl-19-NT)

** [[Propetandrol]] (17α-ethyl-19-NT 3β-propionate)

* Never marketed

** [[Bolenol]] (3-deketo-17α-ethyl-19-nor-5-androstenediol)

** [[Dimethyltrienolone]] (7α,17α-dimethyl-δ^9,11-19-NT)

** [[Ethyldienolone]] (17α-ethyl-δ⁹-19-NT)

** [[Methyldienolone]] (17α-methyl-δ⁹-19-NT)

** [[Methylhydroxynandrolone]] (MOHN, MHN; 4-hydroxy-17α-methyl-19-NT)

** [[Metribolone]] (methyltrienolone, R-1881; 17α-methyl-δ^9,11-19-NT)

** [[Norboletone]] (17α-ethyl-18-methyl-19-NT)

** [[Tetrahydrogestrinone]] (THG; 17α-ethyl-18-methyl-δ^9,11-19-NT)

{{Col-end}}

====Progestins====

{{See also|List of progestogens#Testosterone derivatives}}

Nandrolone, together with [[ethisterone]] (17α-ethynyltestosterone), is also the parent compound of a large group of [[progestin]]s, the [[norethisterone]] (17α-ethynyl-19-nortestosterone) derivatives.<ref name="SchindlerCampagnoli2003">{{cite journal | vauthors = Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH | title = Classification and pharmacology of progestins | journal = Maturitas | volume = 46 | pages = S7–S16 | date = December 2003 | issue = Suppl 1 | pmid = 14670641 | doi = 10.1016/j.maturitas.2003.09.014 }}</ref><ref name="Meikle2003">{{cite book| vauthors = Meikle AW |title=Endocrine Replacement Therapy in Clinical Practice|url=https://books.google.com/books?id=CA0HCAAAQBAJ&pg=PA489|date=24 April 2003|publisher=Springer Science & Business Media|isbn=978-1-59259-375-0|pages=489–|quote=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, [...]}}</ref> This family is subdivided into two groups: the [[estrane]]s and the [[gonane]]s.<ref name="SchindlerCampagnoli2003" /> 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]].<ref name="SchindlerCampagnoli2003" />

===Synthesis===

[[File:19-Nortestosterone synthesis.svg|thumb|right|500px|19-Nortestosterone synthesis:<ref>{{cite journal|doi=10.1021/ja01117a065|title=The Facile Synthesis of 19-Nortestosterone and 19-Norandrostenedione from Estrone|journal=Journal of the American Chemical Society|volume=75|issue=21|pages=5366–5369|year=1953| vauthors = Wilds AL, Nelson NA }}</ref> alternative:<ref>{{cite journal |doi=10.1002/hlca.19630460135 |title=19-Norsteroide II. Ein einfaches Herstellungsverfahren für 19-Norandrostan-Derivate. Über Steroide, 193. Mitteilung |journal=Helvetica Chimica Acta |volume=46 |pages=344–352 |year=1963 | vauthors = Ueberwasser H, Heusler K, Kalvoda J, Meystre CH, Wieland P, Anner G, Wettstein A }}</ref><ref>{{cite journal|doi=10.1016/S0040-4039(00)71440-7|title=Synthesis of optically active (+)-19-nortestosterone by asymmetric bis-annulation reaction|journal=Tetrahedron Letters|volume=21|issue=5|pages=487–490|year=1980| vauthors = Shimizu I, Naito Y, Tsuji J }}</ref>]]

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]],<ref>{{cite journal|doi=10.1039/QR9500400069|title=The reduction of organic compounds by metal-ammonia solutions|journal=Quarterly Reviews, Chemical Society|volume=4|pages=69|year=1950| vauthors = Birch AJ }}</ref> 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====

* Treatment of '''4''' with decanoic anhydride and [[pyridine]] affords ''nandrolone decanoate''.<ref>{{cite patent | inventor = DeWytt ED, Overbeek O, Overbeek GA | country = US | number = 2998423 | gdate = 1961 | assign1 = [[Organon]] }}.</ref>

* Acylation of '''4''' with phenylpropionyl chloride yields ''nandrolone phenpropionate''.<ref>{{cite patent| country = CH| number = 206119 | gdate = 1939 | assign1 = [[:de:Novartis|Gesellschaft für Chemische Industrie Basel]] }}</ref>

===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 [[IOC|International Olympic Committee]] has set a limit of 2.0 μg/L of 19-norandrosterone in urine as the upper limit,<ref>{{cite news | url = http://www.wada-ama.org/en/News-Center/Articles/Clarification-about-Nandrolone-Testing1/ | title = Clarification about Nandrolone Testing | date = 2005-05-30 | publisher = World Anti-Doping Agency | access-date = 2012-01-31 | url-status = dead | archive-url = https://archive.today/20120915060715/http://www.wada-ama.org/en/News-Center/Articles/Clarification-about-Nandrolone-Testing1/ | archive-date = 2012-09-15 }}</ref> beyond which an [[sportsperson|athlete]] is suspected of [[doping in sport|doping]]. In the largest nandrolone study performed on 621 athletes at the [[1998 Winter Olympics|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.<ref name="pmid16597518">{{cite journal | vauthors = Bresson M, Cirimele V, Villain M, Kintz P | title = Doping control for metandienone using hair analyzed by gas chromatography-tandem mass spectrometry | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 836 | issue = 1–2 | pages = 124–8 | date = May 2006 | pmid = 16597518 | doi = 10.1016/j.jchromb.2006.03.040 }}</ref><ref>{{cite journal |vauthors=Ueki M, Ikekita A, Takao Y | title = [Nandrolone metabolite in urine of Nagano Olympic athlete] | journal = Jap. J. For. Tox. | volume = 18 | pages = 198–199 | year = 2000 | language = ja }}</ref><ref name="pmid11086369">{{cite journal | vauthors = Catlin DH, Leder BZ, Ahrens B, Starcevic B, Hatton CK, Green GA, Finkelstein JS | title = Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite | journal = JAMA | volume = 284 | issue = 20 | pages = 2618–21 | year = 2000 | pmid = 11086369 | doi = 10.1001/jama.284.20.2618 | doi-access = free }}</ref><ref name="isbn0-9626523-7-7">{{cite book | vauthors = Baselt RC | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 8th | publisher = Biomedical Publications | location = Foster City, CA | year = 2008 | isbn = 978-0-9626523-7-0 | pages = 1078–1080 | url = http://www.biomedicalpublications.com/ | access-date = 2010-08-19 | archive-date = 2020-12-04 | archive-url = https://web.archive.org/web/20201204114016/http://www.biomedicalpublications.com/ | url-status = dead }}</ref>

A number of nandrolone cases in [[athletics (sport)|athletics]] occurred in 1999, which included high-profile athletes such as [[Merlene Ottey]], [[Dieter Baumann]], and [[Linford Christie]].<ref>{{cite web | title=The Drugs Issue: Baumann to fight all the way | vauthors=Baron P | website=The Telegraph | date=19 September 2000 | url=https://www.telegraph.co.uk/sport/4771735/The-Drugs-Issue-Baumann-to-fight-all-the-way.html | access-date=2010-11-13 | url-access=subscription }}</ref> However, the following year the detection method for nandrolone at the time was proved to be faulty. [[Mark Richardson (athlete)|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.<ref>{{cite news | url = https://www.theguardian.com/sport/2004/feb/19/athletics.comment | title = Athletics: Mark Richardson explains how he felt at his disciplinary hearing | vauthors = Richardson M | date = 2004-02-19 | work = [[The Guardian]] | access-date = 2010-11-13 }}</ref>

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 [[shotput]]ter [[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.<ref>{{cite web | url = https://www.npr.org/2007/10/05/15027417/track-star-marion-jones-to-admit-steroid-use | title = Track Star Marion Jones to Admit Steroid Use | publisher = National Public Radio | date = 2007-10-05 | access-date = 2009-11-09 }}</ref> 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.<ref>{{cite report | author = UK Sport Anti-doping Directorate |date=January 2000 | title = Nandrolone Review | url=http://www.uksport.gov.uk/images/uploaded/nandrevv2.pdf | archive-url = https://web.archive.org/web/20050404200642/http://www.uksport.gov.uk/images/uploaded/nandrevv2.pdf | archive-date=2005-04-04 | publisher=[[UK Sport]] | access-date = 2013-02-02 }}</ref>

[[Mass spectrometry]] is also used to detect small amounts of nandrolone in urine samples.<ref>{{cite journal | vauthors = Buiarelli F, Giannetti L, Jasionowska R, Cruciani C, Neri B | journal=Rapid Communications in Mass Spectrometry | title=Determination of nandrolone metabolites in human urine: comparison between liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry | volume=24 | issue=13 | pages=1881–1894 | date=July 2010 | doi=10.1002/rcm.4583| pmid=20533318 | bibcode=2010RCMS...24.1881B | doi-access=free }}</ref>

==History==

[[File:DECA QV 300.jpg|right|thumb|150px|QV Nandrolone Deca, a form of nandrolone used by athletes.]]

Nandrolone was first [[chemical synthesis|synthesized]] in 1950.<ref name="Elks2014" /><ref name="Schnitzer1967" /><ref name=HemmersbachChapter2009/>{{rp|130}}<ref name="Birch1950">{{cite journal| vauthors = Birch AJ |title=80. Hydroaromatic steroid hormones. Part I. 10-Nortestosterone|journal=Journal of the Chemical Society (Resumed)|year=1950|pages=367|issn=0368-1769|doi=10.1039/jr9500000367}}</ref> It was first introduced, as nandrolone phenylpropionate, in 1959, and then as nandrolone decanoate in 1962, followed by additional esters.<ref>{{cite book|title=Consolidated List of Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments|url=https://books.google.com/books?id=leVCukUgNlsC&pg=PA154|year=1983|publisher=United Nations Publications|isbn=978-92-1-130230-1|pages=154–}}{{Dead link|date=January 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

==Society and culture==

===Generic names===

Nandrolone is the [[generic term|generic name]] of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}, {{abbrlink|DCF|Dénomination Commune Française}}, and {{abbrlink|DCIT|Denominazione Comune Italiana}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA189|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1}}</ref><ref name="Drugs.com">{{cite web | url=https://www.drugs.com/international/nandrolone.html | title=Nandrolone}}</ref> The formal generic names of nandrolone esters include [[nandrolone cyclohexylpropionate]] ({{abbrlink|BANM|British Approved Name}}), [[nandrolone cyclotate]] ({{abbrlink|USAN|United States Adopted Name}}), [[nandrolone decanoate]] ({{abbrlink|USAN|United States Adopted Name|USAN}}, {{abbrlink|USP|United States Pharmacopeia}}, {{abbrlink|BANM|British Approved Name}}, {{abbrlink|JAN|Japanese Accepted Name}}), [[nandrolone laurate]] ({{abbrlink|BANM|British Approved Name}}), [[nandrolone phenpropionate]] ({{abbrlink|USP|United States Pharmacopeia}}), and [[nandrolone phenylpropionate]] ({{abbrlink|BANM|British Approved Name}}, {{abbrlink|JAN|Japanese Accepted Name}}).<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

===Doping in sports===

{{See also|List of doping in sport cases#Nandrolone esters}}

Nandrolone was probably among the first anabolic steroids to be used as a doping agent in sports in the 1960s.{{cn|date=December 2023}} It has been banned at the Olympics since 1974.<ref name=HemmersbachChapter2009>{{cite book| vauthors = Hemmersbach P, Große J | veditors = Thieme D, Hemmersbach P |title=Doping in sports|date=2009|publisher=Springer|location=Berlin|isbn=978-3-540-79088-4|pages=127–154|chapter=Nandrolone: A Multi-Faceted Doping Agent}}</ref>{{rp|128}} There are many known cases of [[doping in sports]] with nandrolone esters by [[professional sports|professional]] [[athlete]]s.

==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 [[bisphosphonate]]s became available.<ref name="pmid27141449">{{cite journal | vauthors = Pan MM, Kovac JR | title = Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness | journal = Translational Andrology and Urology | volume = 5 | issue = 2 | pages = 213–9 | date = April 2016 | pmid = 27141449 | pmc = 4837307 | doi = 10.21037/tau.2016.03.03 | doi-access = free }}</ref> They have also been studied in [[clinical trial]]s for [[chronic kidney failure]], [[aplastic anemia]], and as [[male contraceptive]]s.<ref name=HemmersbachChapter2009/>{{rp|134}}

== References ==

{{Reflist}}

== Further reading ==

{{refbegin}}

* {{cite journal | vauthors = Geusens P | title = Nandrolone decanoate: pharmacological properties and therapeutic use in osteoporosis | journal = Clinical Rheumatology | volume = 14 | pages = 32–9 | date = September 1995 | issue = Suppl 3 | pmid = 8846659 | doi = 10.1007/bf02210686 | s2cid = 24365057 }}

* {{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–21 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}

* {{cite book | vauthors = Hemmersbach P, Grosse J | chapter = Nandrolone: A Multi-Faceted Doping Agent | title = Doping in Sports | volume = 195| issue = <!-- --> | pages = 127–54 | date = 2010 | pmid = 20020363 | doi = 10.1007/978-3-540-79088-4_6 | series = Handbook of Experimental Pharmacology | isbn = 978-3-540-79087-7 }}

* {{cite journal | vauthors = Velema MS, Kwa BH, de Ronde W | title = Should androgenic anabolic steroids be considered in the treatment regime of selected chronic obstructive pulmonary disease patients? | journal = Current Opinion in Pulmonary Medicine | volume = 18 | issue = 2 | pages = 118–24 | date = March 2012 | pmid = 22189453 | doi = 10.1097/MCP.0b013e32834e9001 | s2cid = 6155275 }}

* {{cite journal | vauthors = Busardò FP, Frati P, Sanzo MD, Napoletano S, Pinchi E, Zaami S, Fineschi V | title = The impact of nandrolone decanoate on the central nervous system | journal = Current Neuropharmacology | volume = 13 | issue = 1 | pages = 122–31 | date = January 2015 | pmid = 26074747 | pmc = 4462037 | doi = 10.2174/1570159X13666141210225822 }}

* {{cite journal | vauthors = Wu C, Kovac JR | title = Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health | journal = Current Urology Reports | volume = 17 | issue = 10 | pages = 72 | date = October 2016 | pmid = 27535042 | doi = 10.1007/s11934-016-0629-8 | s2cid = 43199715 }}

* {{cite journal | vauthors = Pan MM, Kovac JR | title = Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness | journal = Translational Andrology and Urology | volume = 5 | issue = 2 | pages = 213–9 | date = April 2016 | pmid = 27141449 | pmc = 4837307 | doi = 10.21037/tau.2016.03.03 | doi-access = free }}

{{refend}}

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