Oxandrolone

{{Short description|Androgen and anabolic steroid}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = verified | verifiedrevid = 462266722 | IUPAC_name = (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isoch | image = Oxandrolone.svg | image_class = skin-invert-image | width = 225px | image2 = Oxandrolone molecule ball.png | image_class2 = bg-transparent | width2 = 235px

| tradename = Oxandrin, Anavar, others<ref name="TradeNames1">{{cite journal | vauthors = Mavros Y, O'Neill E, Connerty M, Bean JF, Broe K, Kiel DP, Maclean D, Taylor A, Fielding RA, Singh MA | title = Oxandrolone Augmentation of Resistance Training in Older Women: A Randomized Trial | journal = Medicine and Science in Sports and Exercise | volume = 47 | issue = 11 | pages = 2257–2267 | date = November 2015 | pmid = 25899102 | doi = 10.1249/MSS.0000000000000690 | quote = Oxandrolone (trade name Anavar or Oxandrin) }}</ref> | Drugs.com = {{drugs.com|monograph|oxandrolone}} | MedlinePlus = a604024 | pregnancy_category = X | legal_BR = C5 | legal_BR_comment = <ref name="Anvisa-2023">{{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_US = Schedule III | routes_of_administration = By mouth | class = Androgen; Anabolic steroid

| bioavailability = 97%<ref name="MozayaniRaymon2003">{{cite book|vauthors=Mozayani A, Raymon L|title=Handbook of Drug Interactions: A Clinical and Forensic Guide|url=https://books.google.com/books?id=dwMyBwAAQBAJ&pg=PA513|date=15 October 2003|publisher=Springer Science & Business Media|isbn=978-1-59259-654-6|pages=513–|access-date=6 November 2017|archive-date=14 January 2023|archive-url=https://web.archive.org/web/20230114000800/https://books.google.com/books?id=dwMyBwAAQBAJ&pg=PA513|url-status=live}}</ref> | protein_bound = 94–97%<ref name="MozayaniRaymon2003" /> | metabolism = Kidneys (primarily), liver<ref name="Hemat2003">{{cite book|vauthors=Hemat RA|title=Andropathy|url=https://books.google.com/books?id=hfwlDwAAQBAJ&pg=PA108|date=2 March 2003|publisher=Urotext|isbn=978-1-903737-08-8|pages=108–|access-date=2017-11-06|archive-date=2023-01-14|archive-url=https://web.archive.org/web/20230114000803/https://books.google.com/books?id=hfwlDwAAQBAJ&pg=PA108|url-status=live}}</ref><ref name="MozayaniRaymon2003" /> | elimination_half-life = Adults: 9.4–10.4 hours<ref name="MozayaniRaymon2003" /><ref name="pmid19170590">{{cite journal | vauthors = Miller JT, Btaiche IF | title = Oxandrolone treatment in adults with severe thermal injury | journal = Pharmacotherapy | volume = 29 | issue = 2 | pages = 213–226 | date = February 2009 | pmid = 19170590 | doi = 10.1592/phco.29.2.213 | hdl-access = free | s2cid = 25780591 | hdl = 2027.42/90285 }}</ref> Elderly: 13.3 hours<ref name="pmid19170590" /> | excretion = Urine: 28% (unchanged)<ref name="pmid19170590" /> Feces: 3%<ref name="pmid19170590" />

| IUPHAR_ligand = 7092 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 53-39-4 | ATC_prefix = A14 | ATC_suffix = AA08 | ATC_supplemental = | PubChem = 5878 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00621 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 5667 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7H6TM3CT4L | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D00462 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 7820 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1200436 | synonyms = Var; CB-8075; NSC-67068; SC-11585; Protivar; 17α-Methyl-2-oxa-4,5α-dihydrotestosterone; 17α-Methyl-2-oxa-DHT; 17α-Methyl-2-oxa-5α-androstan-17β-ol-3-one

| C=19 | H=30 | O=3 | SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(COC(=O)C4)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = QSLJIVKCVHQPLV-PEMPUTJUSA-N }}  '''Oxandrolone''' is an androgen and synthetic anabolic steroid (AAS) medication to help promote weight gain in various situations, to help offset protein catabolism caused by long-term corticosteroid therapy, to support recovery from severe burns, to treat bone pain associated with osteoporosis, to aid in the development of girls with Turner syndrome, and for other indications.<ref name="Llewellyn2011">{{cite book|vauthors=Llewellyn W|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT342|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=342–352|access-date=2017-11-06|archive-date=2024-04-07|archive-url=https://web.archive.org/web/20240407100842/https://books.google.com/books?id=afKLA-6wW0oC&pg=PT342#v=onepage&q&f=false|url-status=live}}</ref><ref name="LiGuo2016" /><ref name="RojasFinnerty2012" /> It is taken by mouth.<ref name="Llewellyn2011" /> It was sold under the brand names Oxandrin and Anavar, among others.<ref name="TradeNames1"/>

The drug is a synthetic androgen and anabolic steroid, hence is an agonist of the androgen receptor (AR), the biological target of androgens such as testosterone and dihydrotestosterone.<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 = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> Side effects of oxandrolone include severe cases of peliosis hepatis, sometimes associated with liver failure and intra-abdominal hemorrhage; liver tumors, sometimes fatal; and blood lipid changes associated with increased risk of atherosclerosis. Additional warnings include the risks associated with cholestatic hepatitis, hypercalcemia in patients with breast cancer, and increased risk for the development of prostatic hypertrophy and prostatic carcinoma in older patients.<ref name="fda923" /> It has strong anabolic effects and weak androgenic effects, which gave it a mild side effect profile in that regard and made it especially suitable for use in women.<ref name="Llewellyn2011" /> Milder side effects in women were increased sexual desire, symptoms of hyperandrogenism such as acne, and symptoms of masculinization such as increased hair growth and voice changes.<ref name="Llewellyn2011" />

Oxandrolone was first described in 1962 and introduced for medical use in 1964.<ref name="Llewellyn2011" /> The drug is a controlled substance in many countries, so non-medical use for purposes such as improving physique and performance has been generally illicit.<ref name="Llewellyn2011" /><ref name="pmid9414081">{{cite journal | vauthors = Korkia P, Stimson GV | title = Indications of prevalence, practice and effects of anabolic steroid use in Great Britain | journal = International Journal of Sports Medicine | volume = 18 | issue = 7 | pages = 557–562 | date = October 1997 | pmid = 9414081 | doi = 10.1055/s-2007-972681 | s2cid = 260169851 | quote = Low dose 28 +/- 18; High dose 80 +/- 13 }}</ref><ref name="FDA2009" /><ref name="CanadaLaws" /><ref name="GovUK" />

In the United States, the FDA's Endocrinologic and Metabolic Drugs Advisory Committee unanimously concluded in 1984 that there was no evidence of efficacy for oxandrolone.<ref name="OxandroloneFDAwithdrawal">{{cite web |title=Gemini Laboratories, LLC, et al.; Withdrawal of Approval of One New Drug Application for OXANDRIN (Oxandrolone) Tablets and Four Abbreviated New Drug Applications for Oxandrolone Tablets |url=https://www.federalregister.gov/documents/2023/06/28/2023-13733/gemini-laboratories-llc-et-al-withdrawal-of-approval-of-one-new-drug-application-for-oxandrin |website=Federal Register |date=28 June 2023 |publisher=Office of the Federal Register of the National Archives and Records Administration |access-date=1 January 2025}}</ref> On March 26, 2019, Gemini asked FDA to withdraw approval for all doses of the drug, stating that they were no longer marketing it.<ref name="fda923" /><ref name="OxandroloneFDAwithdrawal"/> FDA notified Gemini and other license holders on December 16, 2022, that it believed that the potential problems with the drug that the drug were sufficiently serious that it should be removed from the market, citing the 1984 finding of lack of efficacy and the extensive safety warnings and precautions listed on the prescribing information, "including peliosis hepatis, sometimes associated with liver failure and intra-abdominal hemorrhage; liver cell tumors, sometimes fatal; and blood lipid changes that are known to be associated with increased risk of atherosclerosis" as well as "cholestatic hepatitis, hypercalcemia in patients with breast cancer, and increased risk for the development of prostatic hypertrophy and prostatic carcinoma in geriatric patients."<ref name="OxandroloneFDAwithdrawal"/> Gemini and Sandoz requested that the FDA completely withdraw approval for the drug.<ref name="OxandroloneFDAwithdrawal"/>

==Medical uses== Oxandrolone has been researched and prescribed as a treatment for a wide variety of conditions. It was FDA-approved for treating bone pain associated with osteoporosis, aiding weight gain following surgery or physical trauma, during chronic infection, or in the context of unexplained weight loss, and counteracting the catabolic effect of long-term corticosteroid therapy.<ref name="UpsherSmithLabel">{{cite web | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/076761lbl.pdf | title = Oxandrolone Tablets, USP - Rx only | publisher = U.S. Food and Drug Administration | work = Drugs@FDA | date = 1 December 2006 | access-date = 21 June 2016 | archive-date = 26 August 2016 | archive-url = https://web.archive.org/web/20160826023419/https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/076761lbl.pdf }}</ref><ref name="BTGLabel">{{cite web | url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/13718slr022_Oxandrin_lbl.pdf | title=Oxandrin (oxandrolone tablets, USP) | publisher=BTG Pharmaceuticals, U.S. Food and Drug Administration | work=Drugs@FDA | date=21 April 2003 | access-date=21 June 2016 | archive-date=1 March 2017 | archive-url=https://web.archive.org/web/20170301103150/http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/13718slr022_Oxandrin_lbl.pdf | url-status=live }}</ref> Oxandrolone is used to quicken recovery from severe burns.<ref name="LiGuo2016"/><ref name="pmid37403125">{{cite journal |vauthors=Wischmeyer PE, Bear DE, Berger MM, De Waele E, Gunst J, McClave SA, Prado CM, Puthucheary Z, Ridley EJ, Van den Berghe G, van Zanten AR |title=Personalized nutrition therapy in critical care: 10 expert recommendations |journal=Crit Care |volume=27 |issue=1 |article-number=261 |date=July 2023 |pmid=37403125 |doi=10.1186/s13054-023-04539-x |doi-access=free |pmc=10318839 }}</ref><ref name="pmid38746694">{{cite journal |vauthors=Mrazek AA, Simpson P, Lee JO |title=Nutrition in Pediatric Burns |journal=Semin Plast Surg |volume=38 |issue=2 |pages=125–132 |date=May 2024 |pmid=38746694 |doi=10.1055/s-0044-1782648 |pmc=11090660 |url=}}</ref>

In the management of severe burn injuries, clinical trials have demonstrated the therapeutic advantages of oxandrolone, and it was widely adopted as a standard treatment protocol in burn centers globally. Meta-analyses of clinical trials substantiate the efficacy of oxandrolone in severe burn cases: the benefits are manifold and significant, and include a reduction in catabolic weight loss, augmentation of lean body mass, enhancement of donor-site wound healing, and a decrease in the duration of both intensive care unit (ICU) and overall hospital stay. These benefits do not appear to be accompanied by an increased risk of infection, hyperglycemia, or hepatic dysfunction, which underscores the safety profile of oxandrolone in severe burn patient population.<ref name="pmid37403125"/> Data analysis confirms oxandrolone's advantage in promoting skin healing as an adjunct therapy for adult burn patients.<ref name="pmid36127967">{{cite journal |vauthors=Jalkh AP, Eastmond AK, Shetty C, Rizvi SM, Sharaf J, Williams KD, Tariq M, Acharekar MV, Guerrero Saldivia SE, Unnikrishnan SN, Chavarria YY, Akindele AO, Hamid P |title=Oxandrolone Efficacy in Wound Healing in Burned and Decubitus Ulcer Patients: A Systematic Review |journal=Cureus |volume=14 |issue=8 |article-number=e28079 |date=August 2022 |pmid=36127967 |pmc=9477554 |doi=10.7759/cureus.28079 |doi-access=free |url=}}</ref> Oxandrolone improves weight regain, bone mineral density, lean body mass, and accelerates wound healing for donor graft sites.<ref name="pmid31504621">{{cite journal |vauthors=Ring J, Heinelt M, Sharma S, Letourneau S, Jeschke MG |title=Oxandrolone in the Treatment of Burn Injuries: A Systematic Review and Meta-analysis |journal=J Burn Care Res |volume=41 |issue=1 |pages=190–199 |date=January 2020 |article-number=irz155 |pmid=31504621 |doi=10.1093/jbcr/irz155 |url=}}</ref> Oxandrolone was recommended as an adjunctive therapy, alongside insulin, metformin, and closely monitored propranolol, in severe burn patients, for metabolic and nutritional support.<ref name="pmid33834987">{{cite journal |vauthors=Wang L, Chen R, Dong J, Guo Z |title=[Nutrition support in the chronic critically ill patients] |language=Chinese |journal=Zhonghua Wei Zhong Bing Ji Jiu Yi Xue |volume=33 |issue=3 |pages=381–384 |date=March 2021 |pmid=33834987 |doi=10.3760/cma.j.cn121430-20201010-00665 |url=}}</ref><ref name="pmid37149383">{{cite journal |vauthors=Shahrokhi S, Jeschke MG |title=Metabolic and Nutritional Support |journal=Surg Clin North Am |volume=103 |issue=3 |pages=473–482 |date=June 2023 |pmid=37149383 |doi=10.1016/j.suc.2023.01.009 |url=}}</ref> Oxandrolone improves both short-term and long-term outcomes in people recovering from severe burns and was well-established as a safe treatment for this indication.<ref name="LiGuo2016">{{cite journal | vauthors = Li H, Guo Y, Yang Z, Roy M, Guo Q | title = The efficacy and safety of oxandrolone treatment for patients with severe burns: A systematic review and meta-analysis | journal = Burns | volume = 42 | issue = 4 | pages = 717–727 | date = June 2016 | pmid = 26454425 | doi = 10.1016/j.burns.2015.08.023 | s2cid = 24139354 }}</ref><ref name="RojasFinnerty2012">{{cite journal | vauthors = Rojas Y, Finnerty CC, Radhakrishnan RS, Herndon DN | title = Burns: an update on current pharmacotherapy | journal = Expert Opinion on Pharmacotherapy | volume = 13 | issue = 17 | pages = 2485–2494 | date = December 2012 | pmid = 23121414 | pmc = 3576016 | doi = 10.1517/14656566.2012.738195 }}</ref> One of the underlying mechanisms in burn management is that oxandrolone helps reduce hypermetabolic response, which is characterized by increased energy expenditure, elevated stress hormones levels such as cortisol, insulin resistance, muscle wasting, and impaired wound healing; this response is reduced by improving whole-body nitrogen balance as well as preserving lean body mass during recovery.<ref name="pmid35832568">{{cite journal |vauthors=Kopel J, Sorensen G, Griswold J |title=A Reappraisal of Oxandrolone in Burn Management |journal=J Pharm Technol |volume=38 |issue=4 |pages=232–238 |date=August 2022 |pmid=35832568 |pmc=9272491 |doi=10.1177/87551225221091115 |url=}}</ref>

As of 2019, oxandrolone was prescribed off-label for the development of girls with Turner syndrome,<ref name="pmid31684688"/> and counteract wasting of diverse origin.<ref name="pmid31684688"/>

As of 2012, oxandrolone was used in the treatment of idiopathic short stature, anemia, hereditary angioedema,<ref name="pmid22729959">{{cite journal | vauthors = Bork K | title = Current management options for hereditary angioedema | journal = Current Allergy and Asthma Reports | volume = 12 | issue = 4 | pages = 273–280 | date = August 2012 | pmid = 22729959 | doi = 10.1007/s11882-012-0273-4 | s2cid = 207323793 }}</ref> hypogonadism and alcoholic hepatitis.<ref name="pmid22541704">{{cite journal | vauthors = Choi G, Runyon BA | title = Alcoholic hepatitis: a clinician's guide | journal = Clinics in Liver Disease | volume = 16 | issue = 2 | pages = 371–385 | date = May 2012 | pmid = 22541704 | doi = 10.1016/j.cld.2012.03.015 }}</ref>{{Update inline|date=March 2024}}

Medical research established the effectiveness of oxandrolone in aiding the development of girls with Turner syndrome. Although oxandrolone had long been used to accelerate growth in children with idiopathic short stature, it is unlikely to increase adult height, and in some cases may even decrease it;{{citation needed|date=December 2019}} as such, as of 2015, oxandrolone has largely been replaced by growth hormone for this use.<ref name="pmid26051296">{{cite journal | vauthors = Wit JM, Oostdijk W | title = Novel approaches to short stature therapy | journal = Best Practice & Research. Clinical Endocrinology & Metabolism | volume = 29 | issue = 3 | pages = 353–366 | date = June 2015 | pmid = 26051296 | doi = 10.1016/j.beem.2015.01.003 }}</ref>{{Update inline|date=March 2024}} However, a 2019 Cochrane review comparing effects of adding oxandrolone to growth hormone treatment to growth hormone alone found moderate-quality evidence that the addition of oxandrolone led to an increase in final adult height of girls with Turner syndrome, and low-quality evidence showed no increase in adverse effects.<ref name="pmid31684688">{{cite journal | vauthors = Mohamed S, Alkofide H, Adi YA, Amer YS, AlFaleh K | title = Oxandrolone for growth hormone-treated girls aged up to 18 years with Turner syndrome | journal = The Cochrane Database of Systematic Reviews | volume = 2019 | issue = 10 | date = October 2019 | pmid = 31684688 | pmc = 6820693 | doi = 10.1002/14651858.CD010736.pub2 | collaboration = Cochrane Metabolic and Endocrine Disorders Group }}</ref> When the same review assessed the effects of adding oxandrolone to growth hormone treatment on speech, cognition and psychological status, the results were inconclusive due to very-low quality evidence.<ref name="pmid31684688" /> Children with idiopathic short stature or Turner syndrome were given doses of oxandrolone far smaller than those given to people with burns to minimize the likelihood of virilization and premature maturation.<ref name="pmid26051296" /><ref name="SasGault2014">{{cite journal | vauthors = Sas TC, Gault EJ, Bardsley MZ, Menke LA, Freriks K, Perry RJ, Otten BJ, de Muinck Keizer-Schrama SM, Timmers H, Wit JM, Ross JL, Donaldson MD | title = Safety and efficacy of oxandrolone in growth hormone-treated girls with Turner syndrome: evidence from recent studies and recommendations for use | journal = Hormone Research in Paediatrics | volume = 81 | issue = 5 | pages = 289–297 | year = 2014 | pmid = 24776783 | doi = 10.1159/000358195 | doi-access = free }}</ref>{{Incomprehensible inline|date=March 2024|reason=Sources should be used to make verifiable statements, but the sources themselves should not normally be discussed in an article, see WP:MEDSAY - just give a conclusion of the sources without mentioning that a review X found Y (simply say "Y" unless there is a conflict; in case of conflict, follow Wikipedia:These are not original research#Conflict between sources; the sources are of low-quality evidence, don't mention it per WP:MEDRS.)}}

Oxandrolone shows positive effects on cardiometabolic health and visual, motor, and psychosocial functions in adolescent males with preserved testosterone production, such as those with Klinefelter syndrome.<ref name="pmid37149383" />

==Non-medical uses== {{See also|List of doping in sport cases#Oxandrolone}} Oxandrolone has been used illicitly by bodybuilders and athletes for its muscle-building effects as a doping agent in sports. Cases of doping with oxandrolone by professional athletes have been reported.<ref name="Llewellyn2011" /> Because it is more anabolic than androgenic, women and those seeking less intense steroid regimens used it particularly often.<ref name="Llewellyn2011" /> In the past{{when?|date=March 2024}} many{{who?|date=March 2024}} valued oxandrolone's supposed{{clarify|date=March 2024|reason is that supposed low hepatotoxicity true or false?}} low hepatotoxicity relative to most other orally active AASs.<ref name="Llewellyn2011" />

==Contraindications== Like other AASs, oxandrolone may worsen hypercalcemia by increasing osteolytic bone resorption.<ref name="UpsherSmithLabel" /> When taken by pregnant women, oxandrolone may have unintended effects such as masculinization on the fetus.<ref name="UpsherSmithLabel" />

==Side effects== {{See also|Anabolic steroid#Adverse effects}} As of 2004, it was thought that "uniquely" among 17α-alkylated AASs, oxandrolone showed little to no hepatotoxicity, even at high doses.<ref name="pmid15025546">{{cite journal | vauthors = Orr R, Fiatarone Singh M | title = The anabolic androgenic steroid oxandrolone in the treatment of wasting and catabolic disorders: review of efficacy and safety | journal = Drugs | volume = 64 | issue = 7 | pages = 725–750 | year = 2004 | pmid = 15025546 | doi = 10.2165/00003495-200464070-00004 | s2cid = 32262454 }}</ref> However, elevated liver enzymes have been observed in some people, particularly with high doses and/or prolonged treatment, although sometimes returning to normal ranges following discontinuation.<ref name="pmid15025546" /> However, there have been documented severe cases of peliosis hepatis, sometimes associated with liver failure and intra-abdominal hemorrhage; liver tumors, sometimes fatal; and blood lipid changes associated with increased risk of atherosclerosis. This led the FDA to remove approval in June 2023. Additional warnings include the risks associated with cholestatic hepatitis, hypercalcemia in patients with breast cancer, and increased risk for the development of prostatic hypertrophy and prostatic carcinoma in older patients.<ref name="fda923" />

Women who are administered oxandrolone may experience virilization, irreversible development of masculine features such as voice deepening, hirsutism, menstruation abnormalities, male-pattern hair loss, and clitoral enlargement.<ref name="pmid26051296" /><ref name="UpsherSmithLabel" /><ref name="SasGault2014" /> Because of these side effects, doses given to women and children are minimized and people are usually monitored for virilization and growth abnormalities.<ref name="pmid26051296" /><ref name="SasGault2014" /> Like other androgens, oxandrolone can cause or worsen acne and priapism (unwanted or prolonged erections).<ref name="UpsherSmithLabel" /><ref name="medline">{{cite web | url=https://www.medlineplus.gov/druginfo/meds/a604024.html | title=Oxandrolone | publisher=The American Society of Health-System Pharmacists, Inc. | work=MedlinePlus | date=15 May 2016 | access-date=21 June 2016 | archive-date=5 July 2016 | archive-url=https://web.archive.org/web/20160705113245/https://www.nlm.nih.gov/medlineplus/druginfo/meds/a604024.html | url-status=live }}</ref> Oxandrolone can also reduce males' fertility, another side effect common among androgens.<ref name="medline" /> In an attempt to compensate for the exogenous increase in androgens, the body may reduce testosterone production via testicular atrophy and inhibition of gonadotropic activity.<ref name="UpsherSmithLabel" />

Unlike some AASs, oxandrolone does not generally cause gynecomastia because it is not aromatized into estrogenic metabolites.<ref name="CoronaRastrelli2012">{{cite journal | vauthors = Corona G, Rastrelli G, Vignozzi L, Maggi M | title = Emerging medication for the treatment of male hypogonadism | journal = Expert Opinion on Emerging Drugs | volume = 17 | issue = 2 | pages = 239–259 | date = June 2012 | pmid = 22612692 | doi = 10.1517/14728214.2012.683411 | s2cid = 22068249 }}</ref> However, although no reports of gynecomastia were made in spite of widespread use, oxandrolone was reported in a publication in 1991 to have been associated with 33 cases of gynecomastia in adolescent boys treated with it for short stature.<ref name="Aronson2009">{{cite book| vauthors = Aronson JK |title=Meyler's Side Effects of Endocrine and Metabolic Drugs|url=https://books.google.com/books?id=BWMeSwVwfTkC&pg=PA142|date=21 February 2009|publisher=Elsevier|isbn=978-0-08-093292-7|pages=142–}}</ref><ref name="MooreRuvalcaba1991">{{cite journal | vauthors = Moore D, Ruvalcaba R | title = Late Onset Gynecomastia Associated with Oxandrolone Therapy in Adolescents with Short Stature | journal = Journal of Pediatric Endocrinology and Metabolism | volume = 4 | issue = 4 | year = 1991 | doi = 10.1515/JPEM.1991.4.4.249 | issn = 2191-0251 | s2cid = 56669464 }}</ref> The gynecomastia developed during oxandrolone therapy in 19 of the boys and after the therapy was completed in 14 of the boys, and 10 of the boys had transient gynecomastia, while 23 had persistent gynecomastia that necessitated mastectomy.<ref name="Aronson2009" /><ref name="MooreRuvalcaba1991" /> Though transient gynecomastia is a natural and common occurrence in pubertal boys, the gynecomastia associated with oxandrolone was of a late/delayed onset and was persistent in a high percentage of the cases.<ref name="Aronson2009" /><ref name="MooreRuvalcaba1991" /> As such, the researchers stated, "although oxandrolone cannot be implicated as stimulatory [in] gynecomastia", a possible relationship should be considered in clinicians using oxandrolone in adolescents for growth stimulation.<ref name="Aronson2009" /><ref name="MooreRuvalcaba1991" />

== Drug-drug interactions ==

As of 2004 it was known that oxandrolone greatly increases warfarin's blood-thinning effect, sometimes dangerously so.<ref name="demling2004">{{cite web | url=https://www.fda.gov/ohrms/dockets/dailys/04/sep04/092004/04p-0074-sup0001-02-Attachment-01-Demling-vol1.pdf | title=Oxandrolone (Oxandrin) use and the interaction with warfarin | publisher=U.S. Food and Drug Administration | date=September 2004 | access-date=20 June 2016 | vauthors=Demling RH | archive-date=15 February 2017 | archive-url=https://web.archive.org/web/20170215164006/http://www.fda.gov/OHRMS/dockets/dailys/04/sep04/092004/04p-0074-sup0001-02-Attachment-01-Demling-vol1.pdf }}</ref> In April 2004, Savient Pharmaceuticals published a safety alert through the FDA warning healthcare professionals of this.<ref name="warfarin-safety-alert">{{Cite web |date=20 April 2004 |title=Oxandrin (oxandrolone) Dear Healthcare Professional Letter |url=https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm166497.htm |access-date=20 June 2016 |website=Safety Alerts for Human Medical Products |publisher=U.S. Food and Drug Administration |vauthors=Ottery FD |archive-date=21 August 2016 |archive-url=https://web.archive.org/web/20160821134044/http://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm166497.htm }}</ref> Oxandrolone also inhibits the metabolism of oral hypoglycemic agents.<ref name="UpsherSmithLabel" /> It may worsen edema when taken alongside corticosteroids or adrenocorticotropic hormone.<ref name="UpsherSmithLabel" />

==Pharmacology==

===Pharmacodynamics=== {{Relative androgenic to anabolic activity in animals}}

Like other AASs, oxandrolone is an agonist of the androgen receptor, similar to androgens such as testosterone and DHT.<ref name="Llewellyn2011" /> The relative binding affinity of oxandrolone for the androgen receptor is about 0.3% of that of metribolone.<ref name="DaltonGao2010">{{cite book| vauthors = Dalton JT, Gao W |title=Nuclear Receptors |chapter=Androgen Receptor|series=Proteins and Cell Regulation |year=2010|pages=143–182|publisher=Springer |doi=10.1007/978-90-481-3303-1_6|isbn=978-90-481-3302-4}}</ref> Activation of the androgen receptor stimulates protein synthesis, which increases muscle growth, lean body mass, and bone mineral density.<ref name="RojasFinnerty2012" />

Compared to testosterone and many other AASs, oxandrolone is less androgenic relative to its strength as an anabolic.<ref name="Llewellyn2011" /><ref name="katzung">{{cite book | veditors = Katzung BG | vauthors = Chrousos GP | chapter = The Gonadal Hormones & Inhibitors | title = Basic & Clinical Pharmacology | publisher = McGraw-Hill Medical McGraw-Hill distributor | location = New York London | year = 2012 | isbn = 978-0-07-176401-8 | page = 735 }}</ref> Oxandrolone has as much as six times the anabolic potency of testosterone<ref name="Llewellyn2011" /> and has significantly reduced androgenic potency in comparison:<ref name="Llewellyn2011" /> oxandrolone exhibits significantly lower virilizing androgenic properties compared to testosterone, with a relative androgenic potency of only 5%.<ref name="pmid33909503">{{cite journal |vauthors=Knuth CM, Auger C, Jeschke MG |title=Burn-induced hypermetabolism and skeletal muscle dysfunction |journal=Am J Physiol Cell Physiol |volume=321 |issue=1 |pages=C58–C71 |date=July 2021 |pmid=33909503 |pmc=8321793 |doi=10.1152/ajpcell.00106.2021 |url=}}</ref>

Compared to methyltestosterone, oxandrolone has about 322 to 633% of the anabolic potency and 24% of the androgenic potency.<ref name="Llewellyn2011" />

The reduced ratio of anabolic to androgenic activity of oxandrolone motivated its medical use in children and women because less androgenic effect implies less risk of virilization.<ref name="Llewellyn2011" /> The bodybuilding community also considers this fact when choosing between AASs.<ref name="Llewellyn2011" />

As of 2003 and 2011 Oxandrolone was thought to be "uniquely" far less hepatotoxic than other 17α-alkylated AASs, which was thought to be due to differences in metabolism.<ref name="pmid15025546" /><ref name="Llewellyn2011" /><ref name="Hemat2003" /><ref name="pmid19170590" /> This turned out not to be the case in the long run, which is why it was taken off the US market in 2023.<ref name="fda923" />{{improper synthesis|date=March 2024}}{{speculation inline|date=March 2024}}

=== Steroid configuration === {{See also|Steroid}} class=skin-invert-image|thumb|left|upright=0.5|Numbering of carbon atoms up to position 17 in a hypothetical steroid nucleus class=skin-invert-image|thumb|left|upright=0.5|Oxandrolone chemical formula structure

Oxandrolone is based on the tetracyclic steroid framework, which consists of three cyclohexane rings (A, B, and C) and one cyclopentane ring (D). This is a common structure shared by all steroids.<ref name = "IUPAC_steroids">{{cite journal | journal = Pure Appl. Chem. | volume = 61 | issue = 10 | pages = 1783–1822 | year = 1989 | title = Nomenclature of steroids, recommendations 1989 | vauthors = Moss GP, ((the Working Party of the IUPAC-IUB Joint Commission on Biochemical Nomenclature)) | doi = 10.1351/pac198961101783 | s2cid = 97612891 | url = http://iupac.org/publications/pac/pdf/1989/pdf/6110x1783.pdf | access-date = 21 February 2012 | archive-date = 30 November 2012 | archive-url = https://web.archive.org/web/20121130182412/http://iupac.org/publications/pac/pdf/1989/pdf/6110x1783.pdf | url-status = live }}</ref>

The oxygen atom in the lactone bridge replaces a carbon atom at position 2 of the steroid nucleus, classifying oxandrolone as a 2-oxa-steroid. There is a hydroxyl group (-OH) attached at stereo-direction β to carbon 17, which is a characteristic of 17β-hydroxy-steroids.<ref name="pmid10877360">{{cite journal |vauthors=Anthony A, Jaskólski M, Nangia A |title=Crystal chemistry of some synthetic 2-oxa-steroids: conformation, packing motifs and isostructurality |journal=Acta Crystallogr B |volume=56|pages=512–25 |date=June 2000 |issue=3 |pmid=10877360 |doi=10.1107/s0108768199015542}}</ref>

The overall structure of oxandrolone is distinguished by these modifications to the standard steroid nucleus, which contribute to its unique properties as an anabolic steroid. The presence of the lactone bridge, i.e., the 2-oxa-steroid classification, is particularly noteworthy, as it is not commonly found in the steroid family. This structural element is what gives oxandrolone its distinctive chemical identity within the class of anabolic steroids.<ref name="pmid15304998">{{cite journal |vauthors=Ginotra SK, Chhikara BS, Singh M, Chandra R, Tandon V |author-link5=Vibha Tandon|title=Efficient oxidizing methods for the synthesis of oxandrolone intermediates |journal=Chem Pharm Bull (Tokyo) |volume=52 |issue=8 |pages=989–91 |date=August 2004 |pmid=15304998 |doi=10.1248/cpb.52.989}}</ref><ref name="pmid10877360"/> Due to its lactone bridge, oxandrolone is resistant to inactivation by 3α-hydroxysteroid dehydrogenase in skeletal muscle.<ref name="Llewellyn2011" /> This resistance, in contrast to DHT, is believed to underlie oxandrolone's preserved anabolic potency<ref name="Llewellyn2011" />

As oxandrolone is already a 5α-reduced steroid (has a single bond between carbons 4 and 5), it is not a substrate for the 5α-reductase enzyme, hence is not potentiated in androgenic tissues such as the skin, hair follicles, and prostate gland.<ref name="Llewellyn2011" /> In addition, the 5α-reduced state preserves oxandrolone from being a substrate for the aromatase enzyme; therefore, oxandrolone cannot be aromatized into metabolites with estrogenic activity.<ref name="Llewellyn2011" /> Oxandrolone similarly possesses no progestogenic activity.<ref name="Llewellyn2011" />

===Pharmacokinetics=== The oral bioavailability of oxandrolone is 97%.<ref name="MozayaniRaymon2003" /> Its plasma protein binding is 94 to 97%.<ref name="MozayaniRaymon2003" /> The drug is metabolized primarily by the kidneys and to a lesser extent by the liver.<ref name="Hemat2003" /><ref name="MozayaniRaymon2003" /> Oxandrolone is the only AAS that is not primarily or extensively metabolized by the liver, and this is thought to be related to its diminished hepatotoxicity relative to other AASs.<ref name="Hemat2003" /><ref name="pmid19170590" /> Its elimination half-life is reported as 9.4 to 10.4 hours, but is extended to 13.3 hours in the elderly.<ref name="MozayaniRaymon2003" /><ref name="pmid19170590" /> About 28% of an oral dose of oxandrolone is eliminated unchanged in the urine and 3% is excreted in the feces.<ref name="pmid19170590" />

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

Oxandrolone is a synthetic androstane steroid and a 17α-alkylated 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=PA911|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=911–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA767|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=767–}}</ref><ref name="Llewellyn2011" /> It is also known as 2-oxa-17α-methyl-5α-dihydrotestosterone (2-oxa-17α-methyl-DHT) or as 2-oxa-17α-methyl-5α-androstan-17β-ol-3-one, and is DHT with a methyl group at the C17α position and the C2 carbon replaced with an oxygen atom.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> Closely related AASs include the marketed AAS mestanolone (17α-methyl-DHT), oxymetholone (2-hydroxymethylene-17α-methyl-DHT), and stanozolol (a 2,3-pyrazole A ring-fused derivative of 17α-methyl-DHT) and the never-marketed/designer AAS desoxymethyltestosterone (3-deketo-17α-methyl-δ2-DHT), methasterone (2α,17α-dimethyl-DHT), methyl-1-testosterone (17α-methyl-δ1-DHT), and methylstenbolone (2,17α-dimethyl-δ1-DHT).<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />

==History== Oxandrolone was first made by Raphael Pappo and Christopher J. Jung while at Searle Laboratories, now part of Pfizer and they first described the drug in 1962.<ref name="PappoJung1962">{{cite journal| vauthors = Pappo R, Jung CJ |title=2-oxasteroids: A new class of biologically active compounds|journal=Tetrahedron Letters|volume=3|issue=9|year=1962|pages=365–371|issn=0040-4039|doi=10.1016/S0040-4039(00)70883-5}}</ref><ref name="FoxMinot1962">{{cite journal | vauthors = Fox M, Minot AS, Liddle GW | title = Oxandrolone: a potent anabolic steroid of novel chemical configuration | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 22 | issue = 9 | pages = 921–924 | date = September 1962 | pmid = 13894381 | doi = 10.1210/jcem-22-9-921 }}</ref> They were immediately interested in oxandrolone's very weak androgenic effects relative to its anabolic effects.<ref name="PappoJung1962" /> It was introduced as a pharmaceutical drug in the United States in 1964.<ref name="Llewellyn2011" />

It was prescribed to promote muscle regrowth in disorders which cause involuntary weight loss, and is used as part of treatment for HIV/AIDS.<ref name="Llewellyn2011" /> It had also been shown to be partially successful in treating cases of osteoporosis.<ref name="Llewellyn2011" /> However, in 1989, in part due to bad publicity from its illicit use by bodybuilders, production of Anavar was discontinued by Searle Laboratories.<ref name="Llewellyn2011" /> It was picked up by Bio-Technology General Corporation, which changed its name to Savient Pharmaceuticals. In 1995, following successful clinical trials, Savient released it under the brand name ''Oxandrin''.<ref name="Llewellyn2011" /> As of 2011 BTG subsequently had won approvals for orphan drug status by the Food and Drug Administration for treating alcoholic hepatitis, Turner syndrome, and HIV-induced weight loss and as an offset to protein catabolism caused by long-term administration of corticosteroids.<ref name="Llewellyn2011" />

==Society and culture==

===Generic names=== Oxandrolone is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|USP|United States Pharmacopeia}}, {{abbrlink|BAN|British Approved Name}}, {{abbrlink|DCF|Dénomination Commune Française}}, {{abbrlink|DCIT|Denominazione Comune Italiana}}, and {{abbrlink|JAN|Japanese Accepted Name}}, while ''ossandrolone'' is or was formerly the {{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=PA211|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=211–}}</ref><ref name="Drugs.com">{{Cite web |last=Cerner Multum. |date=2023-06-08 |title=Oxandrolone |url=https://www.drugs.com/international/oxandrolone.html |website=drugs.com |access-date=2017-11-12 |archive-date=2017-11-12 |archive-url=https://web.archive.org/web/20171112074139/https://www.drugs.com/international/oxandrolone.html |url-status=live }}</ref><ref name="Organization1982">{{cite book|author=World Health Organization|title=International Nonproprietary Names (INN) for Pharmaceutical Substances: Cumulative List: Dénominations Communes Internationales (DCI) Pour Les Substances Pharmaceutiques: Liste Récapitulative|url=https://books.google.com/books?id=IcUjAQAAMAAJ|year=1982|isbn=978-92-4-056013-0|page=225}}</ref>

===Brand names=== The original brand name of oxandrolone was ''Anavar'', which was marketed in the United States and the Netherlands.<ref name="Llewellyn2011" /><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2935-IA119|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=2935–}}</ref> This product was eventually discontinued and replaced in the United States with a new name of ''Oxandrin'', which as of 2011 was the sole remaining brand name for oxandrolone in the United States.<ref name="Llewellyn2011" /><ref name="Drugs@FDA" /> Oxandrolone has also been sold under the brand names ''Antitriol'' (Spain), ''Anatrophill'' (France), ''Lipidex'' (Brazil), ''Lonavar'' (Argentina, Australia, Italy), Protivar, and ''Vasorome'' (Japan), among others.<ref name="IndexNominum2000" /><ref name="Publishing2013" /><ref name="DEA2011">{{cite book | url=https://commons.wikimedia.org/wiki/File:Drugs_of_Abuse.pdf | title=Drugs of Abuse | publisher=United States Drug Enforcement Administration | year=2011 | page=22 | access-date=2016-06-19 | archive-date=2016-08-22 | archive-url=https://web.archive.org/web/20160822201356/https://commons.wikimedia.org/wiki/File:Drugs_of_Abuse.pdf | url-status=live }}</ref><ref name="Llewellyn2011" /> As of 2016, among those using oxandrolone for nonmedical purposes, it has been referred to colloquially as "Var", a shortened form of the old brand name Anavar.<ref name="LevounisZerbo2016">{{cite book| vauthors = Levounis P, Zerbo E, Aggarwal R |title=Pocket Guide to Addiction Assessment and Treatment|url=https://books.google.com/books?id=caciDAAAQBAJ&pg=PA69|date=3 May 2016|publisher=American Psychiatric Pub|isbn=978-1-61537-072-6|pages=69–}}</ref><ref name="Benavidez2013">{{cite book| vauthors = Benavidez EJ |title=Getting High: The Effects of Drugs|url=https://books.google.com/books?id=M2hCDIXHAiQC&pg=PA39|date=26 February 2013|publisher=Xlibris Corporation|isbn=978-1-4797-9450-8|pages=39–}}</ref> Additional brand names existed for products that were manufactured for the steroid black market.<ref name="Llewellyn2011" />

===Availability===

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

As of 2017, Oxandrolone was one of the few AASs that remained 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 = 11 November 2017 | url = https://www.accessdata.fda.gov/scripts/cder/daf/ | archive-date = 16 November 2016 | archive-url = https://web.archive.org/web/20161116164727/http://www.accessdata.fda.gov/scripts/cder/daf/ | url-status = live }}</ref>

In June 2023, the FDA formally withdrew approval for oxandrolone for all indications, stating that possible adverse effects of the drug were sufficiently serious to warrant removal from the US market. The FDA decision was for reasons of safety or effectiveness, following a 2019 letter from Gemini, a drug manufacturer, stating that the product was no longer being marketed.<ref name="fda923">{{Cite web |last=FDA |date=2023-09-13 |title=Determination That Oxandrin (Oxandrolone) Tablets, 2.5 Milligrams and 10 Milligrams, Were Withdrawn From Sale for Reasons of Safety or Effectiveness |url=https://www.govinfo.gov/content/pkg/FR-2023-09-13/pdf/2023-19796.pdf |access-date=2024-03-18 |website=federalregister.gov |archive-date=2024-03-18 |archive-url=https://web.archive.org/web/20240318101945/https://www.govinfo.gov/content/pkg/FR-2023-09-13/pdf/2023-19796.pdf |url-status=live }}</ref>

As of August 2023, the AASs that remained available for medical use in the US were testosterone, testosterone cypionate, testosterone enanthate, testosterone undecanoate, methyltestosterone, fluoxymesterone, and oxymetholone.<ref name="Drugs@FDA" />

====Other countries==== Generally speaking, the availability of oxandrolone is quite limited.<ref name="Llewellyn2011" /><ref name="Drugs.com" /> It is no longer available in Europe.<ref name="Llewellyn2011" /><ref name="Moldova-2021">{{Cite web|url=https://amdm.gov.md/ro/page/nomenclatorul_de_stat_amed|archive-url=https://web.archive.org/web/20210908183057/https://amdm.gov.md/ro/page/nomenclatorul_de_stat_amed|archive-date=2021-09-08|title=AMED}}</ref> Oxandrolone is available in some less-regulated markets in Asia such as Malaysia and in Mexico.<ref name="Llewellyn2011" />

Historically, oxandrolone has been marketed in Argentina, Australia, Brazil, France, Italy, Japan, and Spain,<ref name="Llewellyn2011" /><ref name="IndexNominum2000" /><ref name="Publishing2013" /> but it appears to no longer be available in these countries.<ref name="Drugs.com" />

===Legal status=== {{See also|Anabolic steroid#Legal status}}

In the United States, oxandrolone was categorized as a Schedule III controlled substance under the Controlled Substances Act along with many other AASs.<ref name="FDA2009">{{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 }}</ref> In 2017, it was a Schedule IV controlled substance in Canada,<ref name="CanadaLaws">{{Cite web|url=http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-15.html|title=Consolidated federal laws of Canada, Controlled Drugs and Substances Act=|author=Legislative Services Branch|website=laws-lois.justice.gc.ca|access-date=2017-01-14|archive-date=2017-02-05|archive-url=https://web.archive.org/web/20170205151428/http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-15.html|url-status=live}}</ref> and a Schedule 4 controlled drug in the United Kingdom.<ref name="GovUK">{{Cite web|url=https://www.gov.uk/government/publications/controlled-drugs-list--2/list-of-most-commonly-encountered-drugs-currently-controlled-under-the-misuse-of-drugs-legislation|title=List of most commonly encountered drugs currently controlled under the misuse of drugs legislation - GOV.UK|website=www.gov.uk|access-date=2017-01-14|archive-date=2019-12-08|archive-url=https://web.archive.org/web/20191208222115/https://www.gov.uk/government/publications/controlled-drugs-list--2/list-of-most-commonly-encountered-drugs-currently-controlled-under-the-misuse-of-drugs-legislation|url-status=live}}</ref>

== References == {{Reflist}}

== External links == {{Commons}} * [https://web.archive.org/web/20071228235918/http://www.savientpharma.com/products/oxandrin.asp Oxandrin Homepage], savientpharma.com (via archive.org) * [https://www.fda.gov/ohrms/dockets/dockets/05p0383/05p-0383-prc0001-03-Labeling-vol1.pdf Oxandrin Label]{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}, fda.gov (retrieved 23 October 2009) * {{cite web |url=https://www.drugs.com/MTM/oxandrolone.html |title=Oxandrolone Side Effects, Interactions and Information |publisher=drugs.com }}

Category:Androgens Category:Androstanes Category:Appetite stimulants Category:Hepatotoxins Category:Delta-lactones Category:Tertiary alcohols Category:Withdrawn drugs