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

{{Short description|Androgen and anabolic steroid}}

{{Redirect-distinguish|Androyd|Android (disambiguation){{!}}Android}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 462267488

| IUPAC_name = (2''Z'',5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[''a'']phenanthren-3-one

| image = Oxymetholone.svg

| width = 250px

<!--Clinical data-->

| Drugs.com = {{drugs.com|CDI|oxymetholone}}

| 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 =

| dependency_liability = Moderate <ref name="d982">{{cite web | title=Anabolic steroid misuse | website=nhs.uk | date=2022-11-04 | url=https://www.nhs.uk/conditions/anabolic-steroid-misuse/ | access-date=2024-07-12}}</ref>

| addiction_liability = Moderate <ref name="d982">{{cite web | title=Anabolic steroid misuse | website=nhs.uk | date=2022-11-04 | url=https://www.nhs.uk/conditions/anabolic-steroid-misuse/ | access-date=2024-07-12}}</ref>

| routes_of_administration = [[Oral administration|By mouth]]

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

<!--Pharmacokinetic data-->

| protein_bound =

| metabolism = [[Liver]]

| elimination_half-life =

| excretion = [[Urine]]

<!--Identifiers-->

| CAS_number = 434-07-1

| ATC_prefix = A14

| ATC_suffix = AA05

| PubChem = 5281034

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB06412

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

| ChemSpiderID = 4444502

| UNII_Ref = {{fdacite||FDA}}

| UNII = L76T0ZCA8K

| = {{|changed|}}

| ChEBI = 7864

| = {{||}}

| KEGG = D00490

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1200585

| synonyms = CI-406; NSC-26198; 2-Hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone; 2-Hydroxymethylene-17α-methyl-DHT; 2-Hydroxymethylene-17α-methyl-5α-androstan-17β-ol-3-one

<!--Chemical data-->| C = 21

| H = 32

| O = 3

| SMILES = O=C4/C(=C\O)C[C@]1([C@@H](CC[C@@H]2[C@@H]1CC[C@]3([C@H]2CC[C@@]3(O)C)C)C4)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12-/t14-,15+,16-,17-,19-,20-,21-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ICMWWNHDUZJFDW-DHODBPELSA-N

<!-- Definition and medical uses -->

'''Oxymetholone''', sold under the brand names '''Anadrol''' and '''Anapolon''' among others, is an [[androgen]] and [[anabolic steroid]] (AAS) medication which is used primarily in the treatment of [[anemia]].<ref name="Llewellyn2011">{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT323|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=323–334}}</ref><ref name="pmid11440282">{{cite journal | vauthors = Pavlatos AM, Fultz O, Monberg MJ, Vootkur A | title = Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid | journal = Clinical Therapeutics | volume = 23 | issue = 6 | pages = 789–801; discussion 771 | date = June 2001 | pmid = 11440282 | doi = 10.1016/s0149-2918(01)80070-9 }}</ref> It is also used to treat [[osteoporosis]], [[HIV/AIDS]] [[wasting syndrome]], and to promote [[weight gain]]<ref>{{Cite web |title=Oxymetholone Powder Uses |url=https://www.aea.ltd/product/oxymetholone-powder/ |access-date=2022-12-17 |website=aea.ltd |language=en-US}}</ref> and [[muscle growth]] in certain situations.<ref name="Llewellyn2011" /> It is taken [[oral administration|by mouth]].<ref name="Llewellyn2011" /><ref name="pmid11440282" />

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

[[Side effect]]s of oxymetholone include increased [[libido|sexual desire]] as well as [[symptom]]s of [[virilization|masculinization]] like [[acne]], [[hirsutism|increased hair growth]], and [[voice deepening|voice changes]].<ref name="Llewellyn2011" /> It can also cause [[hepatotoxicity|liver damage]].<ref name="Llewellyn2011" /><ref name="pmid11440282" /> The drug is a [[synthetic compound|synthetic]] androgen and anabolic steroid and hence is an [[agonist]] 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> It has strong [[anabolic]] effects and weak [[androgen]]ic effects.<ref name="Llewellyn2011" />

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

Oxymetholone was first prescribed in 1959 and was introduced for medical use but shortly after was discontinued due its high lipid toxicity in the year 1961.<ref name="Llewellyn2011" /><ref name="ZdericCarpio1959" /><ref name="ProcRSocMed1961" /><ref name="BrMedJ1961" /> It is used mostly in the [[United States]].<ref name="Llewellyn2011" /><ref name="Drugs.com" /> In addition to its medical use, oxymetholone is used to [[performance-enhancing substance|improve physique and performance]].<ref name="Llewellyn2011" /> The drug is a [[controlled substance]] in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" />

{{TOC limit|3}}

==Medical uses==

The primary clinical applications of oxymetholone include treatment of [[anemia]] and [[osteoporosis]], as well as stimulating [[muscle hypertrophy|muscle growth]] in malnourished or underdeveloped patients.<ref name="Llewellyn2011" /> However, in the [[United States]], the only remaining {{abbrlink|FDA|Food and Drug Administration}}-approved indication is the treatment of [[anemia]].<ref name="Llewellyn2011" /><ref name="AdisInsight">{{Cite web | url=http://adisinsight.springer.com/drugs/800010476 |title = Oxymetholone | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref>

Following the introduction of oxymetholone, [[nonsteroidal]] drugs such as [[epoetin alfa]] were developed and shown to be more effective as a treatment for [[anemia]] and [[osteoporosis]] without the [[side effect]]s of oxymetholone.<ref name="Llewellyn2011" /> The drug remained available despite this and eventually found a new use in treating [[HIV/AIDS]] [[wasting syndrome]].<ref name="Llewellyn2011" />

Presented most commonly as a 50&nbsp;mg [[tablet (pharmacy)|tablet]], oxymetholone has been said to be one of the "strongest" and "most powerful" AAS available for medical use.<ref name="Llewellyn2011" /><ref>{{cite web|url=http://www.meda.us/products/pi/Anadrol-50_PI.pdf|title=Anadrol-50|date=December 2006|publisher=Meda Pharmaceuticals|access-date=8 January 2012|archive-url=https://web.archive.org/web/20140611072023/http://www.meda.us/products/pi/Anadrol-50_PI.pdf|archive-date=11 June 2014|url-status=dead}}</ref> Similarly, there is a risk of [[adverse drug reaction|side effects]].<ref name=drugs1>{{cite web | url = https://www.drugs.com/sfx/oxymetholone-side-effects.html | title = Oxymetholone Side Effects | publisher = drugs.com}}</ref><ref name=drugs2>{{cite web | url = https://www.drugs.com/pro/anadrol.html | title = Anadrol Official FDA Information, Side Effects and Uses | publisher = drugs.com}}</ref> Oxymetholone is highly effective in promoting extensive gains in body mass, mostly by greatly improving protein synthesis.<ref name="Llewellyn2011" /> For this reason, it is often used by [[bodybuilder]]s and [[sportsperson|athlete]]s.<ref name="Llewellyn2011" />

==Non-medical uses==

Oxymetholone is 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}}

The common [[side effect]]s of oxymetholone include [[depression (mood)|depression]], [[lethargy]], [[headache]], [[swelling (medical)|swelling]], fast and excessive [[weight gain]], [[priapism]], changes in skin color, urination problems, [[nausea]], [[vomiting]], [[stomach pain]] (if taken on an empty stomach), [[anorexia (symptom)|loss of appetite]], [[jaundice]], [[gynecomastia|breast swelling]] in men, feeling restless or excited, [[insomnia]], and [[diarrhea]].<ref name=drugs1/> In women, side effects also include [[acne]], changes in [[menstrual period]]s, [[voice deepening]], [[hirsutism|hair growth on the chin or chest]], [[pattern hair loss]], [[clitoromegaly|enlarged clitoris]], and changes in [[libido]].<ref name="Llewellyn2011" /><ref name=drugs1/> Because of its 17α-alkylated structure, oxymetholone is [[hepatotoxic]].<ref name="Llewellyn2011" /> Long term use of the drug can cause a variety of serious ailments, including [[hepatitis]], [[hepatocellular carcinoma|liver cancer]], and [[cirrhosis]]; therefore periodic [[liver function tests]] are recommended for those taking oxymetholone.<ref name=drugs2/>

==Pharmacology==

===Pharmacodynamics===

{{Relative androgenic to anabolic activity in animals}}

Like other AAS, oxymetholone is an [[agonist]] of the [[androgen receptor]] (AR).<ref name="Llewellyn2011" /> It is not a substrate for [[5α-reductase]] (as it is already 5α-reduced) and is a poor substrate for [[3α-hydroxysteroid dehydrogenase]] (3α-HSD), and therefore shows a high ratio of [[anabolic]] to [[androgenic]] activity.<ref name="Llewellyn2011" />

As a DHT derivative, oxymetholone is not a [[substrate (biochemistry)|substrate]] for [[aromatase]] and hence cannot be aromatized into [[estrogen (medication)|estrogen]]ic [[metabolite]]s.<ref name="Llewellyn2011" /> However, uniquely among DHT derivatives, oxymetholone is nonetheless associated with relatively high estrogenicity, and is known to have the potential to produce estrogenic side effects such as [[gynecomastia]] (rarely) and [[water retention (medicine)|water retention]].<ref name="Llewellyn2011" /><ref name="pmid12646793">{{cite journal | vauthors = Hengge UR, Stocks K, Wiehler H, Faulkner S, Esser S, Lorenz C, Jentzen W, Hengge D, Goos M, Dudley RE, Ringham G | display-authors = 6 | title = Double-blind, randomized, placebo-controlled phase III trial of oxymetholone for the treatment of HIV wasting | journal = AIDS | volume = 17 | issue = 5 | pages = 699–710 | date = March 2003 | pmid = 12646793 | doi = 10.1097/00002030-200303280-00008 | s2cid = 29998317 | doi-access = free }}</ref><ref name="CORTESGALLEGOSCASTANEDA1982">{{cite journal | vauthors = Cortesgallegos V, Castaneda G, Alonso R, Perezpasten E, Reyeslugo V, Barron C, Mondragon L, Villalpando S | date = January 1982 | title = Spontaneous and Oxymetholone-Induced Gynecomastia. | journal = Journal of Andrology | volume = 3 | issue = 1 | pages = 33 | publisher = C/O Allen Press, Inc Po Box 368, Lawrence, Ks 66044: Amer Soc Andrology, Inc. }}</ref><ref name="VILLALPANDOMondragon1982">{{cite journal | vauthors = Villalpando S, Mondragon L, Barron C, Reyeslugo U, Perezpasten E, Alonso R, Castaneda G, Gallegos V | title = 5-Alpha Reductase Blockade May Be Responsible for Spontaneous and Oxymetholone-Induced Gynecomastia. | journal = Archivos de Investigacion Medica | date = January 1982 | volume = 13 | issue = 2 | pages = s13 | publisher = Social Apdo Postal 73-032, Mexico Df 03020, Mexico: Inst Mexicano Seguro. }}</ref> It has been suggested that this may be due to direct binding to and activation of the [[estrogen receptor]] by oxymetholone.<ref name="Llewellyn2011" /> Oxymetholone does not possess any significant [[progestogen]]ic activity.<ref name="Llewellyn2011" />

===Pharmacokinetics===

There is limited information available on the [[pharmacokinetics]] of oxymetholone.<ref name="pmid11440282" /> It appears to be [[absorption (pharmacokinetics)|well-absorbed]] with [[oral administration]].<ref name="pmid11440282" /> Oxymetholone has very low [[affinity (pharmacology)|affinity]] for human serum [[sex hormone-binding globulin]] (SHBG), less than 5% of that of testosterone and less than 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> The drug is [[metabolism|metabolized]] in the [[liver]] by [[oxidation]] at the C2 position, [[redox|reduction]] at the C3 position, [[hydroxylation]] at the C17 position, and [[conjugation (biochemistry)|conjugation]].<ref name="pmid11440282" /><ref name="HochadelMosby2015">{{cite book| first1 = Maryanne | last1 = Hochadel | name-list-style = vanc |title=Mosby's Drug Reference for Health Professions|url=https://books.google.com/books?id=IuF1BwAAQBAJ&pg=PA1221|date=1 April 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-31103-8|pages=1221–}}</ref> The C2 hydroxymethylene group of oxymetholone can be [[bond cleavage|cleaved]] to form [[mestanolone]] (17α-methyl-DHT), which may contribute to the effects of oxymetholone.<ref name="Llewellyn2011" /> The [[elimination half-life]] of oxymetholone is unknown.<ref name="HochadelMosby2015" /> Oxymetholone and its [[metabolite]]s are [[elimination (pharmacology)|eliminated]] in the [[urine]].<ref name="pmid6539197" /><ref name="HochadelMosby2015" />

==Chemistry==

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

Oxymetholone, also known as 2-hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone (2-hydroxymethylene-17α-methyl-DHT) or as 2-hydroxymethylene-17α-methyl-5α-androstan-17β-ol-3-one, is a [[synthetic compound|synthetic]] [[androstane]] [[steroid]] and a [[17α-alkylated AAS|17α-alkylated]] [[chemical derivative|derivative]] of DHT.<ref name="Elks2014">{{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&pg=PA924|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=924–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA779|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=779–}}</ref><ref name="Llewellyn2011" />

==History==

Oxymetholone was first described in a 1959 paper by scientists from [[Syntelolname="Llewellyn2011" /><ref name="ZdericCarpio1959">{{cite journal | vauthors = Zderic JA, Carpio H, Ringold HJ |title=Steroids. CVI. Synthesis of 7β-Methyl Hormone Analogs|journal=Journal of the American Chemical Society|date=January 1959|volume=81|issue=2|pages=432–436|doi=10.1021/ja01511a041}}</ref> It was introduced for medical use by [[Syntex]] and [[Imperial Chemical Industries]] in the [[United Kingdom]] under the brand name Anapolon by 1961.<ref name="ProcRSocMed1961">{{cite journal | title = Advertisements | year = 1961 | journal = Proceedings of the Royal Society of Medicine | volume = 54 | issue = 3 | page = XLI | pmc = 1870224 }}</ref><ref name="BrMedJ1961">{{cite journal | title = Advertisements | year = 1961 | journal = British Medical Journal | volume = 1 | issue = 5224 | pmc = 1953122 | url = https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1953122/pdf/brmedj02881-0002.pdf}}</ref> Oxymetholone was also introduced under the brand names Adroyd ([[Parke-Davis]]) by 1961 and Anadrol (Syntex) by 1962.<ref name="Locum1961">{{cite journal | vauthors = Locum R | title = Latest Pharmaceutical Preparations | year = 1961 | journal = The Central African Journal of Medicine | volume = 7 | issue = 11 | pages = 443–444 | url = http://journals.co.za/docserver/fulltext/CAJM/7/11/7355.pdf}}</ref><ref name="pmid13879693">{{cite journal | vauthors = Clark GM | title = New drugs in rheumatic disease | journal = Arthritis and Rheumatism | volume = 5 | issue = 4 | pages = 415–8 | date = August 1962 | pmid = 13879693 | doi = 10.1002/art.1780050411 }}</ref><ref name="Matusow1962">{{cite journal | last = Matusow | first = Paul D | name-list-style = vanc | title = If - Then; C.A.M.S.I.; In the future | journal = Dalhousie Medical Journal | year = 1962 | volume = 15 | issue = 1 | url = http://dalspace.library.dal.ca/bitstream/handle/10222/56103/DMJ.1962.15.1.a01.editorials.pdf}}</ref> The drug was marketed in the [[United States]] in the early 1960s.<ref name="Llewellyn2011" />

==Society and culture==

===Generic names===

''Oxymetholone'' is the [[generic term|generic name]] of the and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|USP|United States Pharmacopeia}}, {{abbrlink|BAN|British Approved Name}}, and {{abbrlink|JAN|Japanese Accepted Name}}, while ''oxymétholone'' is its {{abbrlink|DCF|Dénomination Commune Française}}.<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=PA212|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=212–}}</ref><ref name="Drugs.com">{{Cite web | url=https://www.drugs.com/international/Oxymetholone.html |title = Oxymetholone}}</ref>

===Brand names===

Oxymetholone has been marketed under a variety of brand names including Anadrol, Anadroyd, Anapolon, Anasterona, Anasteronal, Anasterone, Androlic, Androyd, Hemogenin, Nastenon, Oxitoland, Oxitosona, Oxyanabolic, Oxybolone, Protanabol, Roboral, Synasterobe, Synasteron, and Zenalosyn.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="Llewellyn2011" /><ref name="Kochakian2012">{{cite book| first = Charles D. | last = Kochakian | name-list-style = vanc |title=Anabolic-Androgenic Steroids|url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA632|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6|pages=632–}}</ref>

===Availability===

====United States====

{{See also|List of androgens/anabolic steroids available in the United States}}

Oxymetholone is one of the few AAS that remains available for medical use in the [[United States]].<ref name="Drugs@FDA">{{cite web | title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | access-date = 17 December 2016 | url = http://www.accessdata.fda.gov/scripts/cder/daf/}}</ref> The others (as of August 2023) are [[testosterone (medication)|testosterone]], [[testosterone cypionate]], [[testosterone enanthate]], [[testosterone undecanoate]], [[methyltestosterone]], [[fluoxymesterone]], and [[nandrolone]]<ref name="Drugs@FDA" />

====Other countries====

The availability of oxymetholone is fairly limited and seems to be scattered into isolated markets in [[Europe]], [[Asia]], and [[North America|North]] and [[South America]].<ref name="Llewellyn2011" /> It is known to be available in [[Turkey]], [[Greece]], [[Moldova]], [[Iran]], [[Thailand]], [[Brazil]], and [[Paraguay]].<ref name="Llewellyn2011" /><ref name="Drugs.com" /> At least historically, it has also been available in [[Canada]], the [[United Kingdom]], [[Belgium]], the [[Netherlands]], [[Spain]], [[Poland]],The [[United Arab Emirates|UAE]], [[Israel]], [[Hong Kong]], and [[India]].<ref name="IndexNominum2000" />

===Legal status===

Oxymetholone, along with other AAS, is a [[Controlled Substances Act#Schedule III controlled substances|schedule III]] [[controlled substance]] in the [[United States]] under the [[Controlled Substances Act]].<ref name="FFFLM2006">{{cite book| vauthors = Karch SB |title=Drug Abuse Handbook, Second Edition|url=https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30|date=21 December 2006|publisher=CRC Press|isbn=978-1-4200-0346-8|pages=30–}}</ref>

== References ==

{{Reflist}}

== Further reading ==

{{refbegin}}

* {{cite journal | vauthors = Pavlatos AM, Fultz O, Monberg MJ, Vootkur A | title = Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid | journal = Clinical Therapeutics | volume = 23 | issue = 6 | pages = 789–801; discussion 771 | date = June 2001 | pmid = 11440282 | doi = 10.1016/s0149-2918(01)80070-9 }}

{{refend}}

{{Androgens and antiandrogens}}

{{Androgen receptor modulators}}

{{Estrogen receptor modulators}}

[[Category:3β-Hydroxysteroid dehydrogenase inhibitors]]

[[Category:Anabolic–androgenic steroids]]

[[Category:Androstanes]]

[[Category:Hepatotoxins]]

[[Category:Ketones]]

[[Category:Synthetic estrogens]]

[[Category:Tertiary alcohols]]