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{{Drugbox
#REDIRECT [[Androstanolone (disambig)]]
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459443200
| IUPAC_name = (5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[''a'']phenanthren-3-one
| image = Androstanolone.svg
| width = 250
| image2 = Dihydrotestosterone-3D-balls.png
| width2 = 250


<!--Clinical data-->
{{R from move}}
| tradename = Anaboleen, Anabolex, Anaprotin, Andractim, Androlone, Apeton, Gelovit, Neodrol, Ophtovital, Pesomax, Stanaprol, and Stanolone
| pregnancy_category = X
| routes_of_administration = Intramuscular, transdermal

<!--Pharmacokinetic data-->
| bioavailability = Oral: 0–2%{{Citation needed|date=November 2016}}
| metabolism = Hepatic
| elimination_half-life =
| excretion = Renal

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 521-18-6
| ATC_prefix = A14
| ATC_suffix = AA01
| PubChem = 10635
| IUPHAR_ligand = 2856
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02901
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10189
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 08J2K08A3Y
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16330
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 27769

<!--Chemical data-->
| C=19 | H=30 | O=2
| molecular_weight = 290.442 g/mol
| SMILES = O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)CC4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NVKAWKQGWWIWPM-ABEVXSGRSA-N
| synonyms = Stanolone; Dihydrotestosterone; DHT; 5α-Dihydrotestosterone; 5α-DHT
}}
{{About|dihydrotestosterone as a medication|as a natural hormone|Dihydrotestosterone}}

'''Androstanolone''', or '''stanolone''', also known as '''dihydrotestosterone''' ('''DHT'''), is a [[natural product|naturally occurring]] [[anabolic-androgenic steroid]] (AAS) and [[androgen]] [[steroid hormone]] which is used medically in the treatment of male [[hypogonadism]] (androgen deficiency). It is a [[chemical derivative|derivative]] of [[testosterone (medication)|testosterone]], specifically being 5α-dihydrotestosterone, and is a [[potency (pharmacology)|potent]] [[agonist]] of the [[androgen receptor]] (AR). Relative to testosterone, androstanolone is a considerably more potent as an AR agonist.

==Medical uses==
Androstanolone is available in [[pharmaceutical drug|pharmaceutical]] [[drug form|formulation]]s for [[medicine|medical use]] as an androgen and AAS.<ref name="HydeGengenbach2007">{{cite book | first1 = Thomas E. | last1 = Hyde | first2 = Marianne S. | last2 = Gengenbach | name-list-format = vanc | title = Conservative Management of Sports Injuries|url=https://books.google.com/books?id=uzPwfNYyjjUC&pg=PA1100|year=2007|publisher=Jones & Bartlett Learning|isbn=978-0-7637-3252-3|pages=1100–}}</ref> It is used mainly in the treatment of male [[hypogonadism]].<ref name="AdisInsight" />

Androstanolone was under development in a topical formulation for the treatment of [[cachexia]] in [[cancer]] patients, and reached [[Phases of clinical research#Phase III|phase III]] [[clinical trial]]s for this indication, but ultimately was not introduced for this purpose.<ref name="AdisInsight" /> Although androstanolone itself has not been approved for the treatment of cachexia, an [[oral administration|orally active]] synthetic derivative of androstanolone, [[oxandrolone]] (2-oxa-17α-methylandrostanolone), is approved and used for this indication.<ref name="NelmsSucher2010">{{cite book | first1 = Marcia | last1 = Nelms | first2 = Kathryn P. | last2 = Sucher | first3 = Karen | last3 = Lacey | first4 = Sara Long | last4 = Roth | name-list-format = vanc | title = Nutrition Therapy and Pathophysiology|url=https://books.google.com/books?id=rSgIAAAAQBAJ&pg=PT766|date=16 June 2010|publisher=Cengage Learning|isbn=1-133-00809-7|pages=766–}}</ref><ref name="Mantovani2007">{{cite book | first = Giovanni | last = Mantovani | name-list-format = vanc | title = Cachexia and Wasting: A Modern Approach|url=https://books.google.com/books?id=lQyGxrmQ17AC&pg=PA673|date=6 October 2007|publisher=Springer Science & Business Media|isbn=978-88-470-0552-5|pages=673–}}</ref>

==Pharmacology==
Androstanolone is a [[potency (pharmacology)|potent]] [[agonist]] of the AR. It has an [[affinity (pharmacology)|affinity]] (K<sub>d</sub>) of 0.25 to 0.5&nbsp;nM for the human AR, which is about 2- to 3-fold higher than that of [[testosterone]] (K<sub>d</sub> = 0.4 to 1.0&nbsp;nM)<ref name="MozayaniRaymon2011">{{cite book | first1 = Ashraf | last1 = Mozayani | first2 = Lionel | last2 = Raymon | name-list-format = vanc | title = Handbook of Drug Interactions: A Clinical and Forensic Guide | url = https://books.google.com/books?id=NhBJ6kg_uP0C&pg=PA656 | date = 18 September 2011 | publisher = Springer Science & Business Media|isbn=978-1-61779-222-9|pages=656–}}</ref> and the [[dissociation rate]] of androstanolone from the AR is also about 5-fold slower than that of testosterone.<ref>{{cite journal | vauthors = Grino PB, Griffin JE, Wilson JD | title = Testosterone at high concentrations interacts with the human androgen receptor similarly to dihydrotestosterone | journal = Endocrinology | volume = 126 | issue = 2 | pages = 1165–72 | date = February 1990 | pmid = 2298157 | doi = 10.1210/endo-126-2-1165 }}</ref> The [[EC50|EC<sub>50</sub>]] of androstanolone for activation of the AR is 0.13&nbsp;nM, which is about 5-fold stronger than that of testosterone (EC<sub>50</sub> = 0.66&nbsp;nM).<ref>{{cite book | first = Peter A. | last = Wilderer | name-list-format = vanc | title = Treatise on Water Science, Four-Volume Set | chapter = Bioassays for Estrogenic and Androgenic Effects of Water Constituents | url = https://books.google.com/books?id=HSPtBDpRSXMC&pg=PT1805 | date = 1 September 2010 | publisher = Newnes | isbn = 978-0-444-53199-5 | pages = 1805– }}</ref> In [[bioassay]]s, androstanolone has been found to be 2.5- to 10-fold more potent than testosterone.<ref name="MozayaniRaymon2011" />

Unlike testosterone and various other AAS, androstanolone cannot be [[aromatase|aromatized]], and for this reason, poses no risk of [[estrogen]]ic [[side effect]]s like [[gynecomastia]] at any dosage.<ref name="Malven1993">{{cite book | first = Paul V. | last = Malven | name-list-format = vanc | title = Mammalian Neuroendocrinology|url=https://books.google.com/books?id=nZoRPQa_qTkC&pg=PA228|date=12 January 1993|publisher=CRC Press|isbn=978-0-8493-8757-9|pages=228–}}</ref> In addition, androstanolone cannot be [[metabolism|metabolized]] by [[5α-reductase]] (as it is already 5α-reduced), and for this reason, is not potentiated in so-called "androgenic" tissues like the [[skin]], [[hair follicle]]s, and [[prostate gland]]. This provides androstanolone with a greater ratio of [[anabolic]] to [[androgen]]ic effects compared to testosterone, and androstanolone may be less prone to producing certain skin and hair-related side effects like [[acne]], [[oily skin]], [[seborrhea]], [[hirsutism]] (excess facial/body hair growth), and [[androgenic alopecia]] (pattern hair loss), as well as [[prostate enlargement]] (which can lead to [[benign prostatic hyperplasia]]) and an increased risk of [[prostate cancer]].

==Pharmacokinetics==
The [[terminal half-life]] of androstanolone in the body (53&nbsp;minutes) is longer than that of testosterone (34&nbsp;minutes), and this may account for some of the difference in their potency.<ref name="Publishers1999">{{cite journal | vauthors = Diamanti-Kandarakis E | title = Current aspects of antiandrogen therapy in women | journal = Current Pharmaceutical Design | volume = 5 | issue = 9 | pages = 707–23 | year = 1999 | pmid = 10495361 | doi = | url = https://books.google.com/books?id=9rfNZL6oEO0C&pg=PA708}}</ref> A study of transdermal androstanolone and testosterone treatment reported terminal half-lives of 2.83&nbsp;hours and 1.29&nbsp;hours, respectively.<ref name="MozayaniRaymon2003">{{cite book | first1 = Daniel A. | last1 = von Deutsch | first2 = Imad K. | last2 = Abukhalaf | first3 = Rigobert | last3 = Lapu-Bula | editor-first1 = Ashraf | editor-last1 = Mozayani | editor-first2 = Lionel | editor-last2 = Raymon | name-list-format = vanc | chapter = Anabolic Doping Agents | title=Handbook of Drug Interactions: A Clinical and Forensic Guide | url = https://books.google.com/books?id=dwMyBwAAQBAJ&pg=PA510 | date = 15 October 2003 | publisher = Springer Science & Business Media | isbn = 978-1-59259-654-6 | pages = 510– | doi = 10.1007/978-1-61779-222-9_15 }}</ref>

==Chemistry==
{{Main|Dihydrotestosterone#Chemistry}}
{{See also|List of androgen esters#Dihydrotestosterone esters|List of androgens/anabolic steroids}}

Androstanolone, also known as '''5α-androstan-17β-ol-3-one''' or as '''5α-dihydrotestosterone''' ('''5α-DHT'''), is an [[androstane]] [[steroid]] with a [[ketone group]] at the C3 position and a [[hydroxyl group]] at the C17β position. It is the [[chemical derivative|derivative]] of testosterone in which the [[double bond]] between the C4 and C5 positions has been [[redox|reduced]] or [[hydrogenation|hydrogenated]].

Several C17β [[ester]] [[prodrug]]s of DHT, including [[androstanolone benzoate]], [[androstanolone enanthate]], [[androstanolone propionate]], and [[androstanolone valerate]], have been developed and introduced for medical use as AAS.<ref name="Elks2014"/><ref name="MortonHall2012">{{cite book | first1 = I.K. | last1 = Morton | first2 = Judith M. | last2 = Hall | name-list-format = vanc | title = Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA261|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=261–}}</ref>

==History==
Androstanolone was first discovered and synthesized in 1935 by [[Adolf Butenandt]] and his colleagues.<ref name="Schnitzer1967">{{cite book|author=R Schnitzer|title=Experimental Chemotherapy|url=https://books.google.com/books?id=elAJWRnKqDEC&pg=PA156|date=1 January 1967|publisher=Elsevier Science|isbn=978-0-323-14611-1|pages=156–}}</ref><ref name="Krüskemper2013">{{cite book|author=H.-L. Krüskemper|title=Anabolic Steroids|url=https://books.google.com/books?id=4xIlBQAAQBAJ&pg=PA12|date=22 October 2013|publisher=Elsevier|isbn=978-1-4832-6504-9|pages=12–}}</ref>

==Society and culture==

===Generic names===
When used as a drug, it is referred to as androstanolone ([[International Nonproprietary Name|INN]]) or as stanolone ([[British Approved Name|BAN]]).<ref name="HydeGengenbach2007" /><ref name="Elks2014">{{cite book | first = J. | last = Elks | name-list-format = vanc | title = The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=640–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA63|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=63–}}</ref>

===Brand names===
Brand names of androstanolone include Anaboleen, Anabolex, Anaprotin ({{abbr|UK|United Kingdom}}), Andractim (formerly AndroGel-DHT) ({{abbr|FR|France}}, {{abbr|BE|Belgium}}, {{abbr|LU|Luxembourg}}), Androlone, Apeton, Gelovit ({{abbr|ES|Spain}}), Neodrol, Ophtovital, ({{abbr|DE|Germany}}), Pesomax ({{abbr|IT|Italy}}), Stanaprol, and Stanolone, among others.<ref name="HydeGengenbach2007" /><ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="AdisInsight" /><ref name="ListHörhammer2013">{{cite book | first1 = Paul Heinz | last1 = List | first2 = Ludwig | last2 = Hörhammer | name-list-format = vanc | title = Chemikalien und Drogen: Teil B: R, S|url=https://books.google.com/books?id=VXutBgAAQBAJ&pg=PA523|date=12 March 2013|publisher=Springer-Verlag|isbn=978-3-642-66377-2|pages=523–}}</ref>

===Availability===
The availability of pharmaceutical androstanolone is limited; it is not available in the [[United States]] or [[Canada]],<ref name="Drugs@FDA">{{cite web |title=Drugs@FDA: FDA Approved Drug Products |publisher=United States Food and Drug Administration |accessdate=16 November 2016 |url=http://www.accessdata.fda.gov/scripts/cder/daf/}}</ref><ref name="DPD@HealthCanada">{{cite web |title=Drug Product Database - Health Canada |publisher=Health Canada |url=http://www.hc-sc.gc.ca/dhp-mps/prodpharma/databasdon/index-eng.php |accessdate=13 November 2016}}</ref> but is available in certain [[Europe]]an countries, including the [[United Kingdom]], [[Germany]], [[France]], [[Spain]], [[Italy]], [[Belgium]], and [[Luxembourg]].<ref name="IndexNominum2000" /><ref name="AdisInsight">{{cite web | url = https://adisinsight.springer.com/drugs/800011409 | title = Androstanolone Drug Profile | work = Adis Insight | date = 4 December 2006 }}</ref>

The available formulations of androstanolone include [[buccal administration|buccal]] or [[sublingual administration|sublingual]] [[tablet (pharmacy)|tablet]]s (Anabolex, Stanolone), [[topical medication|topical]] [[gel]]s (Andractim, Gelovit, Ophtovital), and, as [[ester]]s in [[oil]], [[injectable]]s like [[dihydrotestosterone propionate]] (Pesomax) and [[dihydrotestosterone valerate]] (Apeton).<ref name="HydeGengenbach2007" /><ref name="AdisInsight" /><ref name="ListHörhammer2013" />

Esters of androstanolone act as [[prodrug]]s of androstanolone in the body and have a long-lasting [[depot injection|depot]] when given via [[intramuscular injection]].<ref name="HydeGengenbach2007" /> [[Dihydrotestosterone benzoate]] (Ermalone-Amp, Hermalone, Sarcosan) and [[dihydrotestosterone enanthate]] (Anaboleen Depot) are additional androstanolone esters that are also available for medical use, while a few others, including [[dihydrotestosterone acetate]], [[dihydrotestosterone butyrate]], and [[dihydrotestosterone formate]], were developed but never marketed.<ref name="Elks2014" />

==References==
{{Reflist|33em}}

{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}
{{GABAA receptor positive allosteric modulators}}

[[Category:Alcohols]]
[[Category:Androgens and anabolic steroids]]
[[Category:Androstanes]]
[[Category:GABAA receptor positive allosteric modulators]]
[[Category:Ketones]]
[[Category:Testosterone]]
[[Category:World Anti-Doping Agency prohibited substances]]

Revision as of 23:51, 30 June 2017

Androstanolone
Clinical data
Trade namesAnaboleen, Anabolex, Anaprotin, Andractim, Androlone, Apeton, Gelovit, Neodrol, Ophtovital, Pesomax, Stanaprol, and Stanolone
Other namesStanolone; Dihydrotestosterone; DHT; 5α-Dihydrotestosterone; 5α-DHT
Pregnancy
category
  • X
Routes of
administration		Intramuscular, transdermal
ATC code
Pharmacokinetic data
BioavailabilityOral: 0–2%[citation needed]
MetabolismHepatic
ExcretionRenal
Identifiers
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H30O2
Molar mass290.442 g/mol g·mol−1
3D model (JSmol)
  • O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)CC4
  • InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1 checkY
  • Key:NVKAWKQGWWIWPM-ABEVXSGRSA-N checkY
 ☒NcheckY (what is this?)  (verify)
This article is about dihydrotestosterone as a medication. For as a natural hormone, see Dihydrotestosterone.

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT), is a naturally occurring anabolic-androgenic steroid (AAS) and androgen steroid hormone which is used medically in the treatment of male hypogonadism (androgen deficiency). It is a derivative of testosterone, specifically being 5α-dihydrotestosterone, and is a potent agonist of the androgen receptor (AR). Relative to testosterone, androstanolone is a considerably more potent as an AR agonist.

Medical uses

Androstanolone is available in pharmaceutical formulations for medical use as an androgen and AAS.[1] It is used mainly in the treatment of male hypogonadism.[2]

Androstanolone was under development in a topical formulation for the treatment of cachexia in cancer patients, and reached phase III clinical trials for this indication, but ultimately was not introduced for this purpose.[2] Although androstanolone itself has not been approved for the treatment of cachexia, an orally active synthetic derivative of androstanolone, oxandrolone (2-oxa-17α-methylandrostanolone), is approved and used for this indication.[3][4]

Pharmacology

Androstanolone is a potent agonist of the AR. It has an affinity (Kd) of 0.25 to 0.5 nM for the human AR, which is about 2- to 3-fold higher than that of testosterone (Kd = 0.4 to 1.0 nM)[5] and the dissociation rate of androstanolone from the AR is also about 5-fold slower than that of testosterone.[6] The EC50 of androstanolone for activation of the AR is 0.13 nM, which is about 5-fold stronger than that of testosterone (EC50 = 0.66 nM).[7] In bioassays, androstanolone has been found to be 2.5- to 10-fold more potent than testosterone.[5]

Unlike testosterone and various other AAS, androstanolone cannot be aromatized, and for this reason, poses no risk of estrogenic side effects like gynecomastia at any dosage.[8] In addition, androstanolone cannot be metabolized by 5α-reductase (as it is already 5α-reduced), and for this reason, is not potentiated in so-called "androgenic" tissues like the skin, hair follicles, and prostate gland. This provides androstanolone with a greater ratio of anabolic to androgenic effects compared to testosterone, and androstanolone may be less prone to producing certain skin and hair-related side effects like acne, oily skin, seborrhea, hirsutism (excess facial/body hair growth), and androgenic alopecia (pattern hair loss), as well as prostate enlargement (which can lead to benign prostatic hyperplasia) and an increased risk of prostate cancer.

Pharmacokinetics

The terminal half-life of androstanolone in the body (53 minutes) is longer than that of testosterone (34 minutes), and this may account for some of the difference in their potency.[9] A study of transdermal androstanolone and testosterone treatment reported terminal half-lives of 2.83 hours and 1.29 hours, respectively.[10]

Chemistry

Main article: Dihydrotestosterone § Chemistry
See also: List of androgen esters § Dihydrotestosterone esters, and List of androgens/anabolic steroids

Androstanolone, also known as 5α-androstan-17β-ol-3-one or as 5α-dihydrotestosterone (5α-DHT), is an androstane steroid with a ketone group at the C3 position and a hydroxyl group at the C17β position. It is the derivative of testosterone in which the double bond between the C4 and C5 positions has been reduced or hydrogenated.

Several C17β ester prodrugs of DHT, including androstanolone benzoate, androstanolone enanthate, androstanolone propionate, and androstanolone valerate, have been developed and introduced for medical use as AAS.[11][12]

History

Androstanolone was first discovered and synthesized in 1935 by Adolf Butenandt and his colleagues.[13][14]

Society and culture

Generic names

When used as a drug, it is referred to as androstanolone (INN) or as stanolone (BAN).[1][11][15]

Brand names

Brand names of androstanolone include Anaboleen, Anabolex, Anaprotin (UK), Andractim (formerly AndroGel-DHT) (FR, BE, LU), Androlone, Apeton, Gelovit (ES), Neodrol, Ophtovital, (DE), Pesomax (IT), Stanaprol, and Stanolone, among others.[1][11][15][2][16]

Availability

The availability of pharmaceutical androstanolone is limited; it is not available in the United States or Canada,[17][18] but is available in certain European countries, including the United Kingdom, Germany, France, Spain, Italy, Belgium, and Luxembourg.[15][2]

The available formulations of androstanolone include buccal or sublingual tablets (Anabolex, Stanolone), topical gels (Andractim, Gelovit, Ophtovital), and, as esters in oil, injectables like dihydrotestosterone propionate (Pesomax) and dihydrotestosterone valerate (Apeton).[1][2][16]

Esters of androstanolone act as prodrugs of androstanolone in the body and have a long-lasting depot when given via intramuscular injection.[1] Dihydrotestosterone benzoate (Ermalone-Amp, Hermalone, Sarcosan) and dihydrotestosterone enanthate (Anaboleen Depot) are additional androstanolone esters that are also available for medical use, while a few others, including dihydrotestosterone acetate, dihydrotestosterone butyrate, and dihydrotestosterone formate, were developed but never marketed.[11]

References

  1. ^ a b c d e Hyde, Thomas E.; Gengenbach, Marianne S. (2007). Conservative Management of Sports Injuries. Jones & Bartlett Learning. pp. 1100–. ISBN 978-0-7637-3252-3. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  2. ^ a b c d e "Androstanolone Drug Profile". Adis Insight. 4 December 2006.
  3. ^ Nelms, Marcia; Sucher, Kathryn P.; Lacey, Karen; Roth, Sara Long (16 June 2010). Nutrition Therapy and Pathophysiology. Cengage Learning. pp. 766–. ISBN 1-133-00809-7. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  4. ^ Mantovani, Giovanni (6 October 2007). Cachexia and Wasting: A Modern Approach. Springer Science & Business Media. pp. 673–. ISBN 978-88-470-0552-5. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  5. ^ a b Mozayani, Ashraf; Raymon, Lionel (18 September 2011). Handbook of Drug Interactions: A Clinical and Forensic Guide. Springer Science & Business Media. pp. 656–. ISBN 978-1-61779-222-9. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  6. ^ Grino PB, Griffin JE, Wilson JD (February 1990). "Testosterone at high concentrations interacts with the human androgen receptor similarly to dihydrotestosterone". Endocrinology. 126 (2): 1165–72. doi:10.1210/endo-126-2-1165. PMID 2298157.
  7. ^ Wilderer, Peter A. (1 September 2010). "Bioassays for Estrogenic and Androgenic Effects of Water Constituents". Treatise on Water Science, Four-Volume Set. Newnes. pp. 1805–. ISBN 978-0-444-53199-5. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  8. ^ Malven, Paul V. (12 January 1993). Mammalian Neuroendocrinology. CRC Press. pp. 228–. ISBN 978-0-8493-8757-9. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  9. ^ Diamanti-Kandarakis E (1999). "Current aspects of antiandrogen therapy in women". Current Pharmaceutical Design. 5 (9): 707–23. PMID 10495361.
  10. ^ von Deutsch, Daniel A.; Abukhalaf, Imad K.; Lapu-Bula, Rigobert (15 October 2003). "Anabolic Doping Agents". In Mozayani, Ashraf; Raymon, Lionel (eds.). Handbook of Drug Interactions: A Clinical and Forensic Guide. Springer Science & Business Media. pp. 510–. doi:10.1007/978-1-61779-222-9_15. ISBN 978-1-59259-654-6. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  11. ^ a b c d Elks, J. (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 640–. ISBN 978-1-4757-2085-3. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  12. ^ Morton, I.K.; Hall, Judith M. (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 261–. ISBN 978-94-011-4439-1. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  13. ^ R Schnitzer (1 January 1967). Experimental Chemotherapy. Elsevier Science. pp. 156–. ISBN 978-0-323-14611-1.
  14. ^ H.-L. Krüskemper (22 October 2013). Anabolic Steroids. Elsevier. pp. 12–. ISBN 978-1-4832-6504-9.
  15. ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 63–. ISBN 978-3-88763-075-1.
  16. ^ a b List, Paul Heinz; Hörhammer, Ludwig (12 March 2013). Chemikalien und Drogen: Teil B: R, S. Springer-Verlag. pp. 523–. ISBN 978-3-642-66377-2. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  17. ^ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 16 November 2016.
  18. ^ "Drug Product Database - Health Canada". Health Canada. Retrieved 13 November 2016.
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