Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol ( D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer prescribed.
of metandienone include of virilization like acne, hirsutism, voice changes, and increased libido, estrogenic effects like fluid retention and gynecomastia, and hepatotoxicity.
Metandienone was originally developed in 1955 by CIBA and marketed in Germany and the United States.
Medical uses
Metandienone was formerly approved and marketed as a form of androgen replacement therapy for the treatment of
hypogonadism in men, but has since been discontinued and withdrawn in most countries, including in the
United States.
It was given at a dosage of 5 to 10 mg/day in men and 2.5 mg/day in women.
Available forms
Metandienone was provided in the form of 2.5, 5 and 10 mg oral tablets.
Non-medical uses
Metandienone is used for physique- and performance-enhancing purposes by
competition ,
, and
.
It is said to be the most widely used AAS for such purposes both today and historically.
Side effects
such as
oily skin,
acne,
seborrhea,
hirsutism, scalp hair loss, and
virilization may occur.
Estrogenic side effects such as
gynecomastia and fluid retention can also occur.
Case reports of gynecomastia exist.
As with other 17α-alkylated steroids, methandienone poses a risk of
hepatotoxicity and use over extended periods of time can result in
cirrhosis without appropriate precautions.
Pharmacology
Pharmacodynamics
Methandienone binds to and activates the androgen receptor (AR) in order to exert its effects.
These include dramatic increases in protein synthesis,
glycogenolysis, and muscle strength over a short space of time. While it can be
metabolism by 5α-reductase into methyl-1-testosterone (17α-methyl-δ
1-DHT), a more potent AAS, the drug has extremely low affinity for this
enzyme and methyl-1-testosterone is thus produced in only trace amounts.
As such, 5α-reductase inhibitors like
finasteride and
dutasteride do not reduce the androgenic effects of metandienone.
Nonetheless, while the ratio of
anabolic to
activity of metandienone is improved relative to that of testosterone, the drug does still possess moderate androgenic activity and is capable of producing severe
virilization in women and children.
As such, it is only really commonly used in men.
Metandienone is a substrate for aromatase and can be metabolism into the estrogen methylestradiol (17α-methylestradiol).
As with other 17α-alkylated AAS, metandienone may be hepatotoxic, especially with prolonged use of high doses.
Pharmacokinetics
Metandienone has high oral
bioavailability.
It has very low affinity for human serum sex hormone-binding globulin (SHBG), about 10% of that of testosterone and 2% of that of DHT.
The drug is
metabolism in the
liver by 6β-
hydroxylation, 3α- and 3β-
oxidation, 5β-reduction, 17-
epimerization, and conjugation among other reactions.
Unlike methyltestosterone, owing to the presence of its C1(2)
double bond, metandienone does not produce 5α-reduced
.
The elimination half-life of metandienone is about 3 to 6 hours.
It is eliminated in the
urine.
Chemistry
Metandienone, also known as 17α-methyl-δ
1-testosterone or as 17α-methylandrost-1,4-dien-17β-ol-3-one, is a synthetic
androstane steroid and a 17α-alkylated derivative of testosterone.
It is a modification of testosterone with a
methyl group at the C17α position and an additional
double bond between the C1 and C2 positions.
The drug is also the 17α-methylated derivative of
boldenone (δ
1-testosterone) and the δ
1 analogue of methyltestosterone (17α-methyltestosterone).
Detection in body fluids
Metandienone is subject to extensive hepatic biotransformation by a variety of enzymatic pathways. The primary urinary metabolites are detectable for up to 3 days, and a recently discovered hydroxymethyl metabolite is found in urine for up to 19 days after a single 5 mg oral dose.
Several of the metabolites are unique to metandienone. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry.
History
Metandienone was first described in 1955.
It was synthesized by researchers at the CIBA laboratories in Basel, Switzerland. CIBA filed for a U.S. patent in 1957,
and began marketing the drug as Dianabol in 1958 in the U.S.
It was initially prescribed to burn victims and the elderly. It was also prescribed off-label as a pharmaceutical performance enhancement to weight lifters and other athletes.
Early adopters included players for Oklahoma University and San Diego Chargers head coach
Sid Gillman, who administered Dianabol to his team starting in 1963.
After the Kefauver Harris Amendment was passed in 1962, the U.S. FDA began the DESI review process to ensure the safety and efficacy of drugs approved under the more lenient pre-1962 standards, including Dianabol.
Following further FDA pressure, CIBA withdrew Dianabol from the U.S. market in 1983.
Society and culture
Generic names
Metandienone is the
generic term of the drug and its , while
methandienone is its and
métandiénone is its .
It is also referred to as
methandrostenolone and as
dehydromethyltestosterone.
The former synonym should not be confused with
methylandrostenolone, which is another name for a different AAS known as
metenolone.
Brand names
Metandienone was introduced and formerly sold primarily under the brand name Dianabol.
It has also been marketed under a variety of other brand names including Anabol, Averbol, Chinlipan, Danabol, Dronabol, Metanabol, Methandon, Naposim, Reforvit-B, and Vetanabol among others.
Legal status
Metandienone, along with other AAS, is a schedule III controlled substance in the
United States under the Controlled Substances Act.
Doping in sports
There are many known cases of doping in sports with metandienone by professional
.
External links
