Androgen and anabolic steroid
"Androyd" redirects here. Not to be confused with
Android .
Oxymetholone
Trade names Anadrol, Anapolon, others Other names 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
AHFS /
Drugs.com
Consumer Drug Information
Pregnancy category
Routes of administration
By mouth
Drug class
Androgen ;
Anabolic steroid
ATC code
Legal status
Bioavailability Well-absorbed
[2]
Metabolism
Liver
[2]
[3]
Elimination half-life Unknown
[3]
Excretion
Urine
[2]
[3]
(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
CAS Number
PubChem
CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.006.454
Formula C 21 H 32 O 3
Molar mass 332.484 g·mol−1 3D model (
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
Y Key:ICMWWNHDUZJFDW-DHODBPELSA-N
Y
N Y
(what is this?)
(verify)
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 .
[4]
[5] It is also used to treat
osteoporosis ,
HIV/AIDS
wasting syndrome , and to promote
weight gain
[6] and
muscle growth in certain situations.
[4] It is taken
by mouth .
[4]
[5]
Side effects of oxymetholone include increased
sexual desire as well as
symptoms of
masculinization like
acne ,
increased hair growth , and
voice changes .
[4] It can also cause
liver damage .
[4]
[5] The drug is a
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).
[4]
[7] It has strong
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
FDA Tooltip Food and Drug Administration -approved indication is the treatment of
anemia .
[4]
[12]
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.
[4] The drug remained available despite this and eventually found a new use in treating
HIV/AIDS
wasting syndrome .
[4]
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.
[4]
[13] Similarly, there is a risk of
side effects .
[14]
[15] Oxymetholone is highly effective in promoting extensive gains in body mass, mostly by greatly improving protein synthesis.
[4] For this reason, it is often used by
bodybuilders and
athletes .
[4]
Non-medical uses
Oxymetholone is used for
physique- and performance-enhancing purposes by
competitive
athletes ,
bodybuilders , and
powerlifters .
[4]
Side 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 .
[14] 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 .
[4]
[14] Because of its 17α-alkylated structure, oxymetholone is
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
Like other AAS, oxymetholone is an
agonist of the
androgen receptor (AR).
[4] 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.
[4]
As a DHT derivative, oxymetholone is not a
substrate for
aromatase and hence cannot be aromatized into
estrogenic
metabolites .
[4] 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 .
[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
pharmacokinetics of oxymetholone.
[5] It appears to be
well-absorbed with
oral administration .
[5] 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.
[2] 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 .
[5]
[3] The C2 hydroxymethylene group of oxymetholone can be
cleaved to form
mestanolone (17α-methyl-DHT), which may contribute to the effects of oxymetholone.
[4] The
elimination half-life of oxymetholone is unknown.
[3] Oxymetholone and its
metabolites are
eliminated in the
urine .
[2]
[3]
Chemistry
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.
[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
generic name of the drug and its
INN Tooltip International Nonproprietary Name ,
USAN Tooltip United States Adopted Name ,
USP Tooltip United States Pharmacopeia ,
BAN Tooltip British Approved Name , and
JAN Tooltip Japanese Accepted Name , while oxymétholone is its
DCF Tooltip 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
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
^
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 .
^
a
b
c
d
e Saartok T, Dahlberg E, Gustafsson JA (June 1984). "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". Endocrinology . 114 (6): 2100–6.
doi :
10.1210/endo-114-6-2100 .
PMID
6539197 .
^
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d
e
f Hochadel M (1 April 2015).
Mosby's Drug Reference for Health Professions . Elsevier Health Sciences. pp. 1221–.
ISBN
978-0-323-31103-8 .
^
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l
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ab
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ad
ae
af
ag
ah William Llewellyn (2011).
Anabolics . Molecular Nutrition Llc. pp. 323–334.
ISBN
978-0-9828280-1-4 .
^
a
b
c
d
e
f Pavlatos AM, Fultz O, Monberg MJ, Vootkur A (June 2001). "Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid". Clinical Therapeutics . 23 (6): 789–801, discussion 771.
doi :
10.1016/s0149-2918(01)80070-9 .
PMID
11440282 .
^
"Oxymetholone Powder Uses" . aea.ltd . Retrieved 2022-12-17 .
^ Kicman AT (June 2008).
"Pharmacology of anabolic steroids" . British Journal of Pharmacology . 154 (3): 502–21.
doi :
10.1038/bjp.2008.165 .
PMC
2439524 .
PMID
18500378 .
^
a
b Zderic JA, Carpio H, Ringold HJ (January 1959). "Steroids. CVI. Synthesis of 7β-Methyl Hormone Analogs". Journal of the American Chemical Society . 81 (2): 432–436.
doi :
10.1021/ja01511a041 .
^
a
b
"Advertisements" . Proceedings of the Royal Society of Medicine . 54 (3): XLI. 1961.
PMC
1870224 .
^
a
b
"Advertisements" (PDF) . British Medical Journal . 1 (5224). 1961.
PMC
1953122 .
^
a
b
c
d
"Oxymetholone" .
^
"Oxymetholone" . AdisInsight . Springer Nature Switzerland AG.
^
"Anadrol-50" (PDF) . Meda Pharmaceuticals. December 2006. Archived from
the original (PDF) on 11 June 2014. Retrieved 8 January 2012 .
^
a
b
c
"Oxymetholone Side Effects" . drugs.com.
^
a
b
"Anadrol Official FDA Information, Side Effects and Uses" . drugs.com.
^ Hengge UR, Stocks K, Wiehler H, Faulkner S, Esser S, Lorenz C, et al. (March 2003).
"Double-blind, randomized, placebo-controlled phase III trial of oxymetholone for the treatment of HIV wasting" . AIDS . 17 (5): 699–710.
doi :
10.1097/00002030-200303280-00008 .
PMID
12646793 .
S2CID
29998317 .
^ 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.
^ 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.
^
a
b
c Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 924–.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d
Index Nominum 2000: International Drug Directory . Taylor & Francis. January 2000. pp. 779–.
ISBN
978-3-88763-075-1 .
^ Locum R (1961).
"Latest Pharmaceutical Preparations" (PDF) . The Central African Journal of Medicine . 7 (11): 443–444.
^ Clark GM (August 1962). "New drugs in rheumatic disease". Arthritis and Rheumatism . 5 (4): 415–8.
doi :
10.1002/art.1780050411 .
PMID
13879693 .
^ Matusow PD (1962).
"If - Then; C.A.M.S.I.; In the future" (PDF) . Dalhousie Medical Journal . 15 (1).
^ Morton IK, Hall JM (6 December 2012).
Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. pp. 212–.
ISBN
978-94-011-4439-1 .
^ Kochakian CD (6 December 2012).
Anabolic-Androgenic Steroids . Springer Science & Business Media. pp. 632–.
ISBN
978-3-642-66353-6 .
^
a
b
"Drugs@FDA: FDA Approved Drug Products" . United States Food and Drug Administration. Retrieved 17 December 2016 .
^ Karch SB (21 December 2006).
Drug Abuse Handbook, Second Edition . CRC Press. pp. 30–.
ISBN
978-1-4200-0346-8 .
Further reading
Pavlatos AM, Fultz O, Monberg MJ, Vootkur A (June 2001). "Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid". Clinical Therapeutics . 23 (6): 789–801, discussion 771.
doi :
10.1016/s0149-2918(01)80070-9 .
PMID
11440282 .
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