Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an

androgen An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes ...

and

anabolic steroid Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor (AR). Anabolism, Anaboli ...

(AAS) medication which is mostly no longer prescribed. It is also used non-medically for physique- and performance-enhancing purposes. It is often taken

by mouth Oral administration is a route of administration whereby a substance is taken through the Human mouth, mouth, swallowed, and then processed via the digestive system. This is a common route of administration for many medications. Oral administ ...

Side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...

s of metandienone include

symptom Signs and symptoms are diagnostic indications of an illness, injury, or condition. Signs are objective and externally observable; symptoms are a person's reported subjective experiences. A sign for example may be a higher or lower temperature ...

s of masculinization like

acne Acne ( ), also known as ''acne vulgaris'', is a long-term Cutaneous condition, skin condition that occurs when Keratinocyte, dead skin cells and Sebum, oil from the skin clog hair follicles. Typical features of the condition include comedo, ...

, increased hair growth,

voice The human voice consists of sound made by a human being using the vocal tract, including talking, singing, laughing, crying, screaming, shouting, humming or yelling. The human voice frequency is specifically a part of human sound produ ...

changes, and increased sexual desire,

estrogen Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three ...

ic effects like fluid retention and breast enlargement, and liver damage. The drug is an

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

of the

androgen receptor The androgen receptor (AR), also known as NR3C4 (nuclear receptor subfamily 3, group C, member 4), is a type of nuclear receptor that is activated by binding any of the androgenic hormones, including testosterone and dihydrotestosterone, in th ...

(AR), the

biological target A biological target is anything within a living organism to which some other entity (like an endogenous ligand or a drug) is directed and/or binds, resulting in a change in its behavior or function. Examples of common classes of biological targets ...

of androgens like

testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...

and dihydrotestosterone (DHT), and has strong anabolic effects and moderate

ic effects. It also has moderate estrogenic effects. Metandienone was originally developed in 1955 by CIBA and marketed in

Germany Germany, officially the Federal Republic of Germany, is a country in Central Europe. It lies between the Baltic Sea and the North Sea to the north and the Alps to the south. Its sixteen States of Germany, constituent states have a total popu ...

and the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

. As the CIBA product Dianabol, metandienone quickly became the first widely used AAS among professional and amateur athletes, and remains the most common orally active AAS for non-medical use. It is currently a controlled substance in the United States and

United Kingdom The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom (UK) or Britain, is a country in Northwestern Europe, off the coast of European mainland, the continental mainland. It comprises England, Scotlan ...

and remains popular among bodybuilders. Metandienone is readily available without a prescription in certain countries such as

Mexico Mexico, officially the United Mexican States, is a country in North America. It is the northernmost country in Latin America, and borders the United States to the north, and Guatemala and Belize to the southeast; while having maritime boundar ...

, and is also manufactured in some

Asia Asia ( , ) is the largest continent in the world by both land area and population. It covers an area of more than 44 million square kilometres, about 30% of Earth's total land area and 8% of Earth's total surface area. The continent, which ...

n countries.

Medical uses

Metandienone was formerly approved and marketed as a form of androgen replacement therapy for the treatment of

hypogonadism Hypogonadism means diminished functional activity of the human gonad, gonads—the testicles or the ovary, ovaries—that may result in diminished biosynthesis, production of sex hormones. Low androgen (e.g., testosterone) levels are referred t ...

in men, but has since been discontinued and withdrawn in most countries, including in the

. 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

competitive Competition is a rivalry where two or more parties strive for a common goal which cannot be shared: where one's gain is the other's loss (an example of which is a zero-sum game). Competition can arise between entities such as organisms, indi ...

athletes, bodybuilders, and powerlifters. It is said to be the most widely used AAS for such purposes both today and historically.

Side effects

Androgen An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes ...

side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...

s such as oily skin,

, seborrhea, increased facial/body hair growth, scalp hair loss, and virilization may occur.

Estrogen Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three ...

ic 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 liver damage without appropriate precautions.

Pharmacology

Pharmacodynamics

Methandienone binds to and activates the

(AR) in order to exert its effects. These include dramatic increases in protein synthesis,

glycogenolysis Glycogenolysis is the breakdown of glycogen (n) to glucose-1-phosphate and glycogen (n-1). Glycogen branches are catabolized by the sequential removal of glucose monomers via phosphorolysis, by the enzyme glycogen phosphorylase. Mechanis ...

, and muscle strength over a short space of time. While it can be metabolized by 5α-reductase into methyl-1-testosterone (17α-methyl-δ¹-DHT), a more potent AAS, the drug has extremely low

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

for this

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

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

ic activity of metandienone is improved relative to that of

, 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 metabolized into the

methylestradiol (17α-methylestradiol). While the rate of aromatization is reduced relative to that for

methyltestosterone Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low ...

, the estrogen produced is metabolism-resistant and hence metandienone retains moderate

ic activity. As such, it can cause side effects such as gynecomastia and fluid retention. The co-administration of an antiestrogen such as an aromatase inhibitor like anastrozole or a selective estrogen receptor modulator like tamoxifen can reduce or prevent such estrogenic side effects. Metandienone has no progestogenic activity. 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

for human serum sex hormone-binding globulin (SHBG), about 10% of that of testosterone and 2% of that of DHT. The drug is metabolized in the

liver The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...

by 6β- hydroxylation, 3α- and 3β-

oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

, 5β-reduction, 17- epimerization, and

conjugation Conjugation or conjugate may refer to: Linguistics *Grammatical conjugation, the modification of a verb from its basic form *Emotive conjugation or Russell's conjugation, the use of loaded language Mathematics *Complex conjugation, the change o ...

among other reactions. Unlike

, owing to the presence of its C1(2) double bond, metandienone does not produce 5α-reduced

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

s. The elimination half-life of metandienone is about 3 to 6 hours. It is eliminated in the

urine Urine is a liquid by-product of metabolism in humans and many other animals. In placental mammals, urine flows from the Kidney (vertebrates), kidneys through the ureters to the urinary bladder and exits the urethra through the penile meatus (mal ...

Chemistry

Metandienone, also known as 17α-methyl-δ¹-testosterone or as 17α-methylandrost-1,4-dien-17β-ol-3-one, is a synthetic androstane

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

and a 17α-alkylated

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

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 (δ¹-testosterone) and the δ¹ analogue of

(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 The San Diego Chargers were a professional American football team in the National Football League (NFL). The Chargers played in San Diego, California from 1961 until 2016, before relocating back to the Greater Los Angeles area, where the franch ...

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 Desi ( or or ; Hindustani language, Hindustani: देसी , , ) also Deshi, is a loose term used to describe the ethnic groups in South Asia, peoples, culture of South Asia, cultures, and products of the Indian subcontinent and their Sout ...

review process to ensure the safety and efficacy of drugs approved under the more lenient pre-1962 standards, including Dianabol. In 1965, the FDA pressured CIBA to further document its legitimate medical uses, and re-approved the drug for treating post-menopausal osteoporosis and pituitary-deficient dwarfism. After CIBA's patent exclusivity period lapsed, other manufacturers began to market generic metandienone in the U.S. Following further FDA pressure, CIBA withdrew Dianabol from the U.S. market in 1983. Generic production shut down two years later, when the FDA revoked metandienone's approval entirely in 1985. Non-medical use was outlawed in the U.S. under the Anabolic Steroids Control Act of 1990. While metandienone is controlled and no longer medically available in the U.S., it continues to be produced and used medically in some other countries.

Society and culture

Generic names

''Metandienone'' is the generic name 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

under the

Controlled Substances Act The Controlled Substances Act (CSA) is the statute establishing federal government of the United States, federal drug policy of the United States, U.S. drug policy under which the manufacture, importation, possession, use, and distribution of ...

Doping in sports

There are many known cases of doping in sports with metandienone by

professional A professional is a member of a profession or any person who work (human activity), works in a specified professional activity. The term also describes the standards of education and training that prepare members of the profession with the partic ...

athletes.

References

External links

{{Estrogen receptor modulators Tertiary alcohols Anabolic–androgenic steroids Androstanes Doping in sport Hepatotoxins Enones Synthetic estrogens Testosterone Veterinary drugs