Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Trenbolone: Difference between pages

{{Short description|Anabolic steroid}}

{{Distinguish|Trestolone}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470612755

| IUPAC_name = (8''S'',13''S'',14''S'',17''S'')-17-Hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1''H''-cyclopenta[''a'']phenanthren-3-one

| image = Trenbolone.svg

| image_class = skin-invert-image

| width = 225px

| image2 = Trenbolone-AugustusMinusOne.png

| image_class2 = bg-transparent

| tradename =

| Drugs.com = {{Drugs.com|international|trenbolone}}

| legal_BR = C5

| legal_BR_comment = {{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}}

| legal_CA = Schedule IV

| legal_US = Schedule III

| legal_status =

| DailyMedID = Trenbolone

| routes_of_administration = [[Intramuscular injection|Intramuscular]] (as [[trenbolone ester|ester]]s)

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

| protein_bound =

| metabolism = [[Liver]]

| elimination_half-life = 6–8 hours{{Citation needed|date=June 2021}}

| excretion = [[Urine]]

| CAS_number = 10161-33-8

| ATC_prefix = None

| ChEBI = 35018

| ChEMBL = 3182355

| KEGG = D08627

| DrugBank = DB11551

| synonyms = Trienolone; Trienbolone; RU-2341; Δ^9,11-Nandrolone; 19-Nor-δ^9,11-testosterone; Estra-4,9,11-trien-17β-ol-3-one

| H = 22

| O = 2

| SMILES = O=C4\C=C2/C(=C1/C=C\[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4

'''Trenbolone''' is an [[androgen]] and [[anabolic steroid]] (AAS) of the [[nandrolone]] group which itself was never marketed for human use. {{Clarify|date=March 2024|what was never marketed—trenbolone, or nandrolone?}}{{cite book|vauthors=Elks J|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|access-date=11 November 2017|archive-date=11 January 2023|archive-url=https://web.archive.org/web/20230111061405/https://books.google.com/books?id=0vXTBwAAQBAJ|url-status=live}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1636|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|page=1591}}{{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=PA279|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=279–|access-date=11 November 2017|archive-date=11 January 2023|archive-url=https://web.archive.org/web/20230111163525/https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA279|url-status=live}}{{Cite web|url=https://www.drugs.com/international/trenbolone.html|title=Trenbolone|access-date=2017-11-11|archive-date=2020-07-07|archive-url=https://web.archive.org/web/20200707053342/https://www.drugs.com/international/trenbolone.html|url-status=live}}{{cite book| vauthors = Llewellyn W |title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT618|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=491–499, 618–,724–}} [[Trenbolone ester]] [[prodrug]]s, including [[trenbolone acetate]] (brand names '''Finajet''', '''Finaplix''', others) and [[trenbolone hexahydrobenzylcarbonate]] (brand names '''Parabolan''', '''Hexabolan'''), are or have been marketed for veterinary and clinical use.{{cite web | title = Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol) | url = http://www.depts.ttu.edu/afs/implantdb/dbhome/Revalor%20Tech%20Bulletin%2012.pdf | publisher = Merck Animal Health | vauthors = Nichols W, Hutcheson J, Streeter M, Corrigan M, Nuttelman B | access-date = 2011-08-22 | archive-date = 2012-10-13 | archive-url = https://web.archive.org/web/20121013190902/http://www.depts.ttu.edu/afs/implantdb/dbhome/Revalor%20Tech%20Bulletin%2012.pdf | url-status = live }}{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }} Trenbolone acetate is used in [[veterinary medicine]] in [[livestock]] to increase [[myotrophy|muscle growth]] and [[appetite]], while trenbolone hexahydrobenzylcarbonate was formerly used clinically in humans but is now no longer marketed. In addition, although it is not approved for clinical or veterinary use, [[trenbolone enanthate]] is sometimes sold on the [[black market]] under the name trenabol.

[[File:A vial of injectable Trenbolone..jpg|thumb|223x223px|A vial of injectable [[trenbolone acetate]]]]

==Uses==

===Veterinary===

Trenbolone, as trenbolone acetate, improves muscle mass, feed efficiency, and mineral absorption in cattle.

==Side effects==

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

Sometimes human users may experience an event called "tren cough" shortly after or during an injection, where the user experiences a violent and extreme coughing fit, which can last for minutes and in some cases even longer.

"Tren cough", despite its name, is not exclusive to trenbolone. It can occur when injecting any oil-steroid solutions, if the solution accidentally is injected intravenously. When the oil-steroid solution gets into the bloodstream, the steroid oil solution travels into the lungs, therefore causing a coughing fit. There are several theories on why this phenomenon happens.{{cite journal | vauthors = Russell M, Storck A, Ainslie M | title = Acute respiratory distress following intravenous injection of an oil-steroid solution | journal = Canadian Respiratory Journal | volume = 18 | issue = 4 | pages = e59–e61 | date = 2011 | doi = 10.1155/2011/743151 | doi-access = free | pmid = 22059184 | pmc = 3205107 }}

It is possible that the androgenic effect from steroids activates a variety of lipid-like active compounds which are called [[Prostaglandin|prostaglandins]].{{cite journal | vauthors = Notelovitz M | title = Androgen effects on bone and muscle | journal = Fertility and Sterility | volume = 77 | issue = Suppl 4 | pages = S34–S41 | date = April 2002 | pmid = 12007900 | doi = 10.1016/s0015-0282(02)02968-0 | doi-access = free }} Many of these prostaglandins are inflammatory and vasoconstrictive. Prostaglandins are signalled through two varying pathways [[Cyclooxygenase|cyclooxygenase (COX)]] (Also known as: [[prostaglandin-endoperoxide synthase]]) and [[Lipoxygenase|lipoxygenases (LOX)]] (also known as: [[EC 1.13.11.34]], [[EC 1.13.11.33]], etc.).{{cite journal | vauthors = Kam PC, See AU | title = Cyclo-oxygenase isoenzymes: physiological and pharmacological role | journal = Anaesthesia | volume = 55 | issue = 5 | pages = 442–449 | date = May 2000 | pmid = 10792135 | doi = 10.1046/j.1365-2044.2000.01271.x }} The bradykinin peptide is well known to promote a cough reaction associated with [[ACE inhibitor]] medications prescribed for [[hypertension]].{{cite journal | vauthors = Fox AJ, Lalloo UG, Belvisi MG, Bernareggi M, Chung KF, Barnes PJ | title = Bradykinin-evoked sensitization of airway sensory nerves: a mechanism for ACE-inhibitor cough | journal = Nature Medicine | volume = 2 | issue = 7 | pages = 814–817 | date = July 1996 | pmid = 8673930 | doi = 10.1038/nm0796-814 }}

==Pharmacology==

===Pharmacodynamics===

Trenbolone has both [[anabolic]] and [[androgenic]] effects. Once [[metabolized]], trenbolone esters have the effect of increasing [[ammonium]] ion uptake by muscles, leading to an increase in the rate of [[protein synthesis]]. It may also have the secondary effects of stimulating appetite and decreasing the rate of [[catabolism]], as all [[anabolic steroids]] are believed to; however, catabolism likely increases significantly once the steroid is no longer taken.{{Cite book | vauthors = Fahey TD | chapter = Anabolic Steroids: Mechanisms and Effects | title = Encyclopedia of sports medicine and science. Internet Society for Sport Science | date = March 1998 | chapter-url = http://www.sportsci.org/encyc/anabster/anabster.html | access-date = 2011-08-23 | archive-date = 2011-08-23 | archive-url = https://web.archive.org/web/20110823213449/http://www.sportsci.org/encyc/anabster/anabster.html | url-status = live }} At least one study in rats has shown trenbolone to cause gene expression of the [[androgen receptor]] (AR) at least as potent as [[dihydrotestosterone]] (DHT). This evidence tends to indicate trenbolone can cause an increase in male [[secondary sex characteristic]]s without the need to convert to a more potent androgen in the body.{{cite journal | vauthors = Wilson VS, Lambright C, Ostby J, Gray LE | title = In vitro and in vivo effects of 17beta-trenbolone: a feedlot effluent contaminant | journal = Toxicological Sciences | volume = 70 | issue = 2 | pages = 202–211 | date = December 2002 | pmid = 12441365 | doi = 10.1093/toxsci/70.2.202 | doi-access = free }}

Studies on metabolism are mixed, with some studies showing that it is metabolized by [[aromatase]] into [[estrogen (medication)|estrogen]]ic compounds, or by [[5α-reductase]] into 5α-reduced androgenic compounds.{{cite journal | vauthors = Yarrow JF, McCoy SC, Borst SE | title = Tissue selectivity and potential clinical applications of trenbolone (17beta-hydroxyestra-4,9,11-trien-3-one): A potent anabolic steroid with reduced androgenic and estrogenic activity | journal = Steroids | volume = 75 | issue = 6 | pages = 377–389 | date = June 2010 | pmid = 20138077 | doi = 10.1016/j.steroids.2010.01.019 | s2cid = 205253265 }}{{cite journal | vauthors = Gettys TW, D'Occhio MJ, Henricks DM, Schanbacher BD | title = Suppression of LH secretion by oestradiol, dihydrotestosterone and trenbolone acetate in the acutely castrated bull | journal = The Journal of Endocrinology | volume = 100 | issue = 1 | pages = 107–112 | date = January 1984 | pmid = 6361192 | doi = 10.1677/joe.0.1000107 }}

The potency of trenbolone is not known, although it's often falsely believed to be five times higher than [[Testosterone (medication)|testosterone]].{{Cite book | vauthors = Llewellyn W | url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT618 |title=Anabolics |date=2011 |publisher=Molecular Nutrition Llc |isbn=978-0-9828280-1-4 |language=en}}{{Cite book | vauthors = Wiebe JP |chapter = The microenvironment in health and cancer of the mammary gland | veditors = Mascie-Taylor CG, Rosetta L | chapter-url=https://books.google.com/books?id=7eVVK3vfAc0C&pg=PA69 |title=Reproduction and Adaptation: Topics in Human Reproductive Ecology|date=2011-01-13 |publisher=Cambridge University Press |isbn=978-1-139-49430-4 |language=en | page = 69 }} This is based on a book by William Llewellyn but has not been definitively proven. Trenbolone was never approved for human use, and therefore limited data on the subject exists. The relevant studies are usually done in rats, which makes the 500/100 potency number inaccurate. Rats respond differently and are less sensitive to androgens. While some literature report a 5 fold higher potency, two other scientific reviews report a 3 fold higher potency.{{cite journal | vauthors = Neumann F | title = Pharmacological and endocrinological studies on anabolic agents | journal = Environmental Quality and Safety. Supplement | issue = 5 | pages = 253–264 | date = 1976 | pmid = 782871 }}{{cite journal | vauthors = Yarrow JF, McCoy SC, Borst SE | title = Tissue selectivity and potential clinical applications of trenbolone (17beta-hydroxyestra-4,9,11-trien-3-one): A potent anabolic steroid with reduced androgenic and estrogenic activity | journal = Steroids | volume = 75 | issue = 6 | pages = 377–389 | date = June 2010 | pmid = 20138077 | doi = 10.1016/j.steroids.2010.01.019 }} Trenbolone also binds with high [[affinity (pharmacology)|affinity]] to the [[progesterone receptor]],{{cite book |url=https://books.google.com/books?id=7eVVK3vfAc0C&pg=PA69 |title=Reproduction and Adaptation: Topics in Human Reproductive Ecology |vauthors=Nicholas Mascie-Taylor CG, Rosetta L |date=13 January 2011 |publisher=Cambridge University Press |isbn=978-1-139-49430-4 |pages=69–}}{{cite book|title=APMIS.: Supplementum|url=https://books.google.com/books?id=szFYAAAAYAAJ|year=2001|publisher=Munksgaard|page=5339|isbn = 9788716164575}}{{cite book| vauthors = McKerns KW |title=Reproductive Processes and Contraception|url=https://books.google.com/books?id=JM6oBwAAQBAJ&pg=PA171|date=13 March 2013|publisher=Springer Science & Business Media|isbn=978-1-4684-3824-6|pages=171–}} and binds to the [[glucocorticoid receptor]] as well.

===Pharmacokinetics===

To prolong its [[elimination half-life]], trenbolone is administered as a [[prodrug]] as an [[ester]] conjugate such as [[trenbolone acetate]], [[trenbolone enanthate]], or [[trenbolone hexahydrobenzylcarbonate]]. Plasma [[lipase]]s then cleave the ester group in the bloodstream leaving free trenbolone.{{citation needed|date=June 2016}}

Trenbolone and 17-epitrenbolone are both excreted in urine as conjugates that can be hydrolyzed with beta-glucuronidase.{{cite journal | vauthors = Schänzer W | title = Metabolism of anabolic androgenic steroids | journal = Clinical Chemistry | volume = 42 | issue = 7 | pages = 1001–1020 | date = July 1996 | pmid = 8674183 | doi = 10.1093/clinchem/42.7.1001 | doi-access = free }} This implies that trenbolone leaves the body as beta-[[glucuronide]]s or [[sulfate]]s.

==Chemistry==

{{See also|List of androgens/anabolic steroids}}

Trenbolone, also known as 19-nor-δ^9,11-testosterone or as estra-4,9,11-trien-17β-ol-3-one, is a [[synthetic compound|synthetic]] [[estrane]] [[steroid]] and a [[chemical derivative|derivative]] of [[nandrolone]] (19-nortestosterone). It is specifically nandrolone with two additional [[double bond]]s in the steroid nucleus. [[Trenbolone ester]]s, which have an [[ester]] at the C17β position, include [[trenbolone acetate]], [[trenbolone enanthate]], [[trenbolone hexahydrobenzylcarbonate]], and [[trenbolone undecanoate]].{{Cite journal| vauthors = Borodi G, Turza A, Camarasan PA, Ulici A |date=2020|title=Structural studies of Trenbolone, Trenbolone Acetate, Hexahydrobenzylcarbonate and Enanthate esters|journal=Journal of Molecular Structure|volume=1212|article-number=128127|doi=10.1016/j.molstruc.2020.128127|bibcode=2020JMoSt121228127B|s2cid=216299984|issn=0022-2860}}

{| class="wikitable"

|+Basic information about different types steroids included base trenbolone inside structure.

!Name:

!Trenbolone

![[Trenbolone acetate]]

![[Trenbolone enanthate]]

![[Trenbolone hexahydrobenzylcarbonate]]

(cyclohexylmethylcarbonate)

|-

|Structural

|[[File:Trenbolone.svg|class=skin-invert-image|frameless]]

|[[File:Trenbolone acetate.svg|class=skin-invert-image|frameless]]

|[[File:Trenbolone enanthate.svg|class=skin-invert-image|frameless]]

|[[File:Trenbolone cyclohexylmethylcarbonate.svg|class=skin-invert-image|frameless]]

|-

|Formula

|C₁₈H₂₂O₂

|C₂₀H₂₄O₃

|C₂₅H₃₄O₃

|C₂₆H₃₄O₄

|-

|Crystal system

|

|monocrystalic

|monocrystalic

|monocrystalic

|-

|Elimination half-life

|48–72 hours{{citation needed|date=October 2020}}

|short

1–2 days; 3 days{{Cite book| vauthors = Ruiz P, Strain EC |url=https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358|title=Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook|date=2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-60547-277-5|language=en}}

|long

11 days

|8 days

|}

==History==

Trenbolone was first [[chemical synthesis|synthesized]] in 1963.{{cite journal | vauthors = Schänzer W | title = Metabolism of anabolic androgenic steroids | journal = Clinical Chemistry | volume = 42 | issue = 7 | pages = 1001–1020 | date = July 1996 | pmid = 8674183 | doi = 10.1093/clinchem/42.7.1001 | doi-access = free }}

==Society and culture==

===Generic names===

''Trenbolone'' is the [[generic term|generic name]] of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}}. It has also been referred to as ''trienolone'' or ''trienbolone'' or tren.{{cite book|author=Food and Agriculture Organization of the United Nations|title=Residues of Some Veterinary Drugs in Animals and Foods: Monographs Prepared by the Thirty-Fourth Meeting of the Joint FAO/WHO Expert Committee on Food Additives, Geneva, 30 January-8 February 1989|url=https://books.google.com/books?id=BCw1OUlrT-QC&pg=PA88|year=1990|publisher=Food & Agriculture Org.|isbn=978-92-5-102933-6|pages=88–}}

===Legal status===

Some [[bodybuilder]]s and [[athlete]]s use trenbolone hexahydrobenzylcarbonate and other esters (acetate, enanthate) for their muscle-building and otherwise performance-enhancing effects.{{Cite web|url = https://athletway.com/articles/trenbolone-hexahydrobenzylcarbonate-use-in-bodybuilding|title = Trenbolone hexahydrobenzylcarbonate use in bodybuilding|date = 20 November 2021|access-date = 24 November 2021|archive-date = 24 November 2021|archive-url = https://web.archive.org/web/20211124032823/https://athletway.com/articles/trenbolone-hexahydrobenzylcarbonate-use-in-bodybuilding|url-status = usurped}} Such use is illegal in the United States and several European and Asian countries. The DEA classifies trenbolone and its esters as [[Controlled Substances Act#Schedule III controlled substances|Schedule III controlled substance]]s under the [[Controlled Substances Act]].{{cite web | title=Controlled Substances Act | url=https://www.fda.gov/regulatoryinformation/legislation/ucm148726.htm | publisher=United States Food and Drug Administration | date=11 June 2009 | access-date=17 June 2016 | archive-date=2 March 2017 | archive-url=https://web.archive.org/web/20170302014716/https://www.fda.gov/regulatoryinformation/legislation/ucm148726.htm | url-status=dead }} Trenbolone is classified as a Schedule 4 drug in [[Canada]]{{cite web |url=http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-24.html?term=steroids#sched4 |title=Controlled Drugs and Substances Act |website=laws-lois.justice.gc.ca |url-status=dead |archive-url=https://web.archive.org/web/20120915015257/http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-24.html?term=steroids |archive-date=2012-09-15}} and a class C drug with no penalty for personal use or possession in the [[United Kingdom]].{{cite web | title = Consideration of the Anabolic Steroids | location = London | publisher = Advisory Council on the Misuse of Drugs | date = September 2010 | url = http://www.homeoffice.gov.uk/publications/alcohol-drugs/drugs/acmd1/anabolic-steroids-report/anabolic-steroids?view=Binary. | archive-url = https://web.archive.org/web/20110922230656/http://www.homeoffice.gov.uk/publications/alcohol-drugs/drugs/acmd1/anabolic-steroids-report/anabolic-steroids?view=Binary | archive-date = 2011-09-22 }} Use or possession of steroids without a prescription is a crime in [[Australia]].{{Cite web |url=http://www.aic.gov.au/en/crime_types/drugs_alcohol/drug_types/steroids.aspx |title=Australian Institute of Criminology - Steroids |access-date=2011-08-22 |archive-date=2012-03-23 |archive-url=https://web.archive.org/web/20120323114641/http://www.aic.gov.au/en/crime_types/drugs_alcohol/drug_types/steroids.aspx |url-status=dead }}

===Doping in sports===

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

There are known cases of doping in sports with trenbolone esters by [[professional sports|professional]] [[athlete]]s.

==Environmental persistence==

Early studies suggested that the metabolites of trenbolone acetate would degrade through [[phototransformation]]. However, a 2013 paper found that the [[Endocrine disruptor|endocrine-disrupting]] metabolites were able to reform at night, resulting in a diurnal cycling of the compounds.{{cite journal | vauthors = Qu S, Kolodziej EP, Long SA, Gloer JB, Patterson EV, Baltrusaitis J, Jones GD, Benchetler PV, Cole EA, Kimbrough KC, Tarnoff MD, Cwiertny DM | title = Product-to-parent reversion of trenbolone: unrecognized risks for endocrine disruption | journal = Science | volume = 342 | issue = 6156 | pages = 347–351 | date = October 2013 | pmid = 24072818 | doi = 10.1126/science.1243192 | pmc = 4096139 }} The environmental persistence of the steroid metabolites results in the contamination of water supplies and the disruption of aquatic reproductive processes. Due to its nocturnal reformation, researchers have referred to trenbolone as the "vampire steroid".{{cite news |title='Vampire Steroid' Could Threaten Water Supply: How Does Trenbolone Reawaken In The Absence Of Sunlight?|url=https://www.medicaldaily.com/vampire-steroid-could-threaten-water-supply-how-does-trenbolone-reawaken-absence-sunlight-258301 |work=Medical Daily |date=September 27, 2013}}{{cite news |last1=Gravitz |first1=Lauren |title='Vampire' Steroids Rise After Dark |url=https://www.discovermagazine.com/environment/vampire-steroids-rise-after-dark |work=Discover Magazine |date=April 8, 2014 |language=en}}

== See also ==

* [[Metribolone]]

== References ==

{{Reflist}}

== Further reading ==

{{refbegin}}

* {{cite journal | vauthors = Meyer HH | title = Biochemistry and physiology of anabolic hormones used for improvement of meat production | journal = APMIS | volume = 109 | issue = 1 | pages = 1–8 | date = January 2001 | pmid = 11297191 | doi = 10.1111/j.1600-0463.2001.tb05785.x | s2cid = 23149070 }}

* {{cite journal | vauthors = Yarrow JF, McCoy SC, Borst SE | title = Tissue selectivity and potential clinical applications of trenbolone (17beta-hydroxyestra-4,9,11-trien-3-one): A potent anabolic steroid with reduced androgenic and estrogenic activity | journal = Steroids | volume = 75 | issue = 6 | pages = 377–389 | date = June 2010 | pmid = 20138077 | doi = 10.1016/j.steroids.2010.01.019 | s2cid = 205253265 }}

{{refend}}

{{Androgens and antiandrogens}}

{{Progestogens and antiprogestogens}}

{{Androgen receptor modulators}}

{{Progesterone receptor modulators}}

[[Category:Androgens]]

[[Category:Estranes]]

[[Category:Ketones]]

[[Category:Progestogens]]

[[Category:Secondary alcohols]]