Oxymetholone

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

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 effects of oxymetholone. The drug remained available despite this and eventually found a new use in treating HIV/AIDS wasting syndrome.

Presented most commonly as a 50 mg tablet, oxymetholone has been said to be one of the "strongest" and "most powerful" AAS available for medical use.{{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}} Similarly, there is a risk of side effects.{{cite web | url = https://www.drugs.com/sfx/oxymetholone-side-effects.html | title = Oxymetholone Side Effects | publisher = drugs.com}}{{cite web | url = https://www.drugs.com/pro/anadrol.html | title = Anadrol Official FDA Information, Side Effects and Uses | publisher = drugs.com}} Oxymetholone is highly effective in promoting extensive gains in body mass, mostly by greatly improving protein synthesis. For this reason, it is often used by bodybuilders and athletes.

Oxymetholone is used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.

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

The common side effects of oxymetholone include depression, lethargy, headache, swelling, fast and excessive weight gain, priapism, changes in skin color, urination problems, nausea, vomiting, stomach pain (if taken on an empty stomach), loss of appetite, jaundice, breast swelling in men, feeling restless or excited, insomnia, and diarrhea. In women, side effects also include acne, changes in menstrual periods, voice deepening, hair growth on the chin or chest, pattern hair loss, enlarged clitoris, and changes in libido. Because of its 17α-alkylated structure, oxymetholone is hepatotoxic. Long term use of the drug can cause a variety of serious ailments, including hepatitis, liver cancer, and cirrhosis; therefore periodic liver function tests are recommended for those taking oxymetholone.

{{Relative androgenic to anabolic activity in animals}}

Like other AAS, oxymetholone is an agonist of the androgen receptor (AR). 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.

As a DHT derivative, oxymetholone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites. 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.{{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 }}{{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. }}{{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. }} It has been suggested that this may be due to direct binding to and activation of the estrogen receptor by oxymetholone. Oxymetholone does not possess any significant progestogenic activity.

There is limited information available on the pharmacokinetics of oxymetholone. It appears to be well-absorbed with oral administration. Oxymetholone has very low affinity for human serum sex hormone-binding globulin (SHBG), less than 5% of that of testosterone and less than 1% of that of DHT.{{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 }} The drug is metabolized in the liver by oxidation at the C2 position, reduction at the C3 position, hydroxylation at the C17 position, and conjugation.{{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–}} The C2 hydroxymethylene group of oxymetholone can be cleaved to form mestanolone (17α-methyl-DHT), which may contribute to the effects of oxymetholone. The elimination half-life of oxymetholone is unknown. Oxymetholone and its metabolites are eliminated in the urine.

{{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 androstane steroid and a 17α-alkylated derivative of DHT.{{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–}}{{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–}}

Oxymetholone was first described in a 1959 paper by scientists from Syntex.{{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}} It was introduced for medical use by Syntex and Imperial Chemical Industries in the United Kingdom under the brand name Anapolon by 1961.{{cite journal | title = Advertisements | year = 1961 | journal = Proceedings of the Royal Society of Medicine | volume = 54 | issue = 3 | page = XLI | pmc = 1870224 }}{{cite journal | title = Advertisements | year = 1961 | journal = British Medical Journal | volume = 1 | issue = 5224 | pmc = 1953122 }} Oxymetholone was also introduced under the brand names Adroyd (Parke-Davis) by 1961 and Anadrol (Syntex) by 1962.{{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}}{{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 }}{{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}} The drug was marketed in the United States in the early 1960s.

Oxymetholone 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}}, and {{abbrlink|JAN|Japanese Accepted Name}}, while oxymétholone is its {{abbrlink|DCF|Dénomination Commune Française}}.{{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–}}{{Cite web | url=https://www.drugs.com/international/Oxymetholone.html |title = Oxymetholone}}

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.{{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–}}

{{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.{{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/}} The others (as of August 2023) are testosterone, testosterone cypionate, testosterone enanthate, testosterone undecanoate, methyltestosterone, fluoxymesterone, and nandrolone

The availability of oxymetholone is fairly limited and seems to be scattered into isolated markets in Europe, Asia, and North and South America. It is known to be available in Turkey, Greece, Moldova, Iran, Thailand, Brazil, and Paraguay. At least historically, it has also been available in Canada, the United Kingdom, Belgium, the Netherlands, Spain, Poland,The UAE, Israel, Hong Kong, and India.

Oxymetholone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.{{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–}}

{{Reflist}}

{{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

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