Oxymetholone

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Oxymetholone
Clinical data
Trade namesAnadrol, Anapolon, others
Other namesCI-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
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
  • X
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityWell-absorbed[2]
MetabolismLiver[2][3]
Elimination half-lifeUnknown[3]
ExcretionUrine[2][3]
Identifiers
  • (2Z,5S,8R,9S,10S,13S,14S,17S)-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
JSmol)
  • 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
  • InChI=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 checkY
  • Key:ICMWWNHDUZJFDW-DHODBPELSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an

muscle growth in certain situations.[4] It is taken by mouth.[4][5]

anabolic effects and weak androgenic effects.[4]

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.[4][8][9][10] It is used mostly in the United States.[4][11] In addition to its medical use, oxymetholone is used to improve physique and performance.[4] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[4]

Medical uses

The primary clinical applications of oxymetholone include treatment of anemia and osteoporosis, as well as stimulating muscle growth in malnourished or underdeveloped patients.[4] However, in the United States, the only remaining FDATooltip Food and Drug Administration-approved indication is the treatment of anemia.[4][12]

Following the introduction of oxymetholone,

wasting syndrome.[4]

Presented most commonly as a 50 mg

athletes.[4]

Non-medical uses

Oxymetholone is used for

powerlifters.[4]

Side effects

See also: Anabolic steroid § Adverse effects

The common

hepatotoxic.[4] 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.[15]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

Like other AAS, oxymetholone is an

androgenic activity.[4]

As a DHT derivative, oxymetholone is not a

water retention.[4][16][17][18] It has been suggested that this may be due to direct binding to and activation of the estrogen receptor by oxymetholone.[4] Oxymetholone does not possess any significant progestogenic activity.[4]

Pharmacokinetics

There is limited information available on the

elimination half-life of oxymetholone is unknown.[3] Oxymetholone and its metabolites are eliminated in the urine.[2][3]

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

derivative of DHT.[19][20][4]

History

Oxymetholone was first described in a 1959 paper by scientists from Syntex.[4][8] It was introduced for medical use by Syntex and Imperial Chemical Industries in the United Kingdom under the brand name Anapolon by 1961.[9][10] Oxymetholone was also introduced under the brand names Adroyd (Parke-Davis) by 1961 and Anadrol (Syntex) by 1962.[21][22][23] The drug was marketed in the United States in the early 1960s.[4]

Society and culture

Generic names

Oxymetholone is the

INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, USPTooltip United States Pharmacopeia, BANTooltip British Approved Name, and JANTooltip Japanese Accepted Name, while oxymétholone is its DCFTooltip Dénomination Commune Française.[19][20][24][11]

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.[19][20][11][4][25]

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.[26] The others (as of August 2023) are testosterone, testosterone cypionate, testosterone enanthate, testosterone undecanoate, methyltestosterone, fluoxymesterone, and nandrolone[26]

Other countries

The availability of oxymetholone is fairly limited and seems to be scattered into isolated markets in Europe, Asia, and North and South America.[4] It is known to be available in Turkey, Greece, Moldova, Iran, Thailand, Brazil, and Paraguay.[4][11] 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.[20]

Legal status

Oxymetholone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[27]

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^
    PMID 6539197
    .
  3. ^
    ISBN 978-0-323-31103-8
    .
  4. ^
    ISBN 978-0-9828280-1-4
    .
  5. ^
    PMID 11440282
    .
  6. ^ "Oxymetholone Powder Uses". aea.ltd. Retrieved 2022-12-17.
  7. PMID 18500378
    .
  8. ^
    doi:10.1021/ja01511a041
    .
  9. ^
    PMC 1870224
    .
  10. ^
    PMC 1953122
    .
  11. ^ a b c d "Oxymetholone".
  12. ^ "Oxymetholone". AdisInsight. Springer Nature Switzerland AG.
  13. ^ "Anadrol-50" (PDF). Meda Pharmaceuticals. December 2006. Archived from the original (PDF) on 11 June 2014. Retrieved 8 January 2012.
  14. ^ a b c "Oxymetholone Side Effects". drugs.com.
  15. ^ a b "Anadrol Official FDA Information, Side Effects and Uses". drugs.com.
  16. S2CID 29998317
    .
  17. ^ Cortesgallegos V, Castaneda G, Alonso R, Perezpasten E, Reyeslugo V, Barron C, Mondragon L, Villalpando S (January 1982). "Spontaneous and Oxymetholone-Induced Gynecomastia". Journal of Andrology. 3 (1). C/O Allen Press, Inc Po Box 368, Lawrence, Ks 66044: Amer Soc Andrology, Inc.: 33.
  18. ^ Villalpando S, Mondragon L, Barron C, Reyeslugo U, Perezpasten E, Alonso R, Castaneda G, Gallegos V (January 1982). "5-Alpha Reductase Blockade May Be Responsible for Spontaneous and Oxymetholone-Induced Gynecomastia". Archivos de Investigacion Medica. 13 (2). Social Apdo Postal 73-032, Mexico Df 03020, Mexico: Inst Mexicano Seguro.: s13.
  19. ^
    ISBN 978-1-4757-2085-3
    .
  20. ^
    ISBN 978-3-88763-075-1
    .
  21. ^ Locum R (1961). "Latest Pharmaceutical Preparations" (PDF). The Central African Journal of Medicine. 7 (11): 443–444.
  22. PMID 13879693
    .
  23. ^ Matusow PD (1962). "If - Then; C.A.M.S.I.; In the future" (PDF). Dalhousie Medical Journal. 15 (1).
  24. ISBN 978-94-011-4439-1
    .
  25. ISBN 978-3-642-66353-6
    .
  26. ^ a b "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 17 December 2016.
  27. ISBN 978-1-4200-0346-8
    .

Further reading

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