Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an
androgen
An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This in ...
and
anabolic steroid (AAS) medication which is used mainly in the treatment of
anemia
Anemia or anaemia (British English) is a blood disorder in which the blood has a reduced ability to carry oxygen due to a lower than normal number of red blood cells, or a reduction in the amount of hemoglobin. When anemia comes on slowly, t ...
due to
bone marrow failure.
It is taken
by mouth
Oral administration is a route of administration where a substance is taken through the mouth. Per os abbreviated to P.O. is sometimes used as a direction for medication to be taken orally. Many medications are taken orally because they are i ...
.
Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.
A related drug,
metenolone enanthate
Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It ...
, is given by
injection into muscle.
Side effect
In medicine, a side effect is an effect, whether therapeutic or adverse, that is secondary to the one intended; although the term is predominantly employed to describe adverse effects, it can also apply to beneficial, but unintended, consequence ...
s of metenolone acetate include
symptoms of
masculinization like
acne
Acne, also known as ''acne vulgaris'', is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and ...
,
increased hair growth,
voice changes
'
A voice change or voice mutation, sometimes referred to as a voice break or voice crack, commonly refers to the deepening of the voice of men as they reach puberty. Before puberty, both sexes have roughly similar vocal pitch, but during puberty ...
, and increased
sexual desire
Sexual desire is an emotion and motivational state characterized by an interest in sexual objects or activities, or by a drive to seek out sexual objects or to engage in sexual activities. It is an aspect of sexuality, which varies significantly f ...
.
The drug is a
synthetic androgen and anabolic steroid and hence is an
agonist of the
androgen receptor (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 sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...
and
dihydrotestosterone
Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues includ ...
(DHT).
It has moderate
anabolic
Anabolism () is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking ...
effects and weak
androgen
An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This in ...
ic effects, as well as no
estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...
ic effects or risk of
liver damage
Liver disease, or hepatic disease, is any of many diseases of the liver. If long-lasting it is termed chronic liver disease. Although the diseases differ in detail, liver diseases often have features in common.
Signs and symptoms
Some of the si ...
.
Metenolone enanthate is a
metenolone ester
This is a list of androgen esters, including esters (as well as ethers) of natural androgens like testosterone and dihydrotestosterone (DHT) and synthetic anabolic–androgenic steroids (AAS) like nandrolone (19-nortestosterone).
Esters of nat ...
and a
prodrug of
metenolone
Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate (brand name Primobolan, Nibal) and metenolone enanthate (brand name Primobolan Depot, Nibal Injection). Meten ...
in the body.
Metenolone acetate was introduced for medical use in 1961.
In addition to its medical use, metenolone acetate is used to
improve physique and performance.
The drug is a
controlled substance
A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Single ...
in many countries and so non-medical use is generally illicit.
It remains marketed for medical use only in a few countries, such as
Japan and
Moldova
Moldova ( , ; ), officially the Republic of Moldova ( ro, Republica Moldova), is a landlocked country in Eastern Europe. It is bordered by Romania to the west and Ukraine to the north, east, and south. The unrecognised state of Transnistr ...
.
Side effects
Pharmacology
Chemistry
Metenolone acetate, or metenolone 17β-acetate, is a
synthetic androstane
Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane.
File:androstane.png, 5α-Androstane
File:androstane 5beta.png, 5β-Androstane
Pharmacology ...
steroid and a
derivative
In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...
of DHT.
It is the C17β
acetate ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...
of
metenolone
Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate (brand name Primobolan, Nibal) and metenolone enanthate (brand name Primobolan Depot, Nibal Injection). Meten ...
, which itself is 1-methyl-δ
1-4,5α-dihydrotestosterone (1-methyl-δ
1-DHT) or 1-methyl-5α-androst-1-en-17β-ol-3-one.
History
Metenolone acetate was first introduced for medical use in
West Germany
West Germany is the colloquial term used to indicate the Federal Republic of Germany (FRG; german: Bundesrepublik Deutschland , BRD) between its formation on 23 May 1949 and the German reunification through the accession of East Germany on 3 O ...
in 1961 under the brand name Primobolan and in the United States in 1962.
Society and culture
Generic names
''Metenolone acetate'' is the
generic name of the drug and its , while ''methenolone acetate'' is its and .
Brand names
Metenolone acetate is or has been marketed under a number of brand names including Primobolan, Primobolan S, Primonabol, and Nibal.
Availability
Metenolone acetate is marketed in
Japan and
Moldova
Moldova ( , ; ), officially the Republic of Moldova ( ro, Republica Moldova), is a landlocked country in Eastern Europe. It is bordered by Romania to the west and Ukraine to the north, east, and south. The unrecognised state of Transnistr ...
.
References
External links
*
{{Androgen receptor modulators
Acetate esters
Androgen esters
Androgens and anabolic steroids
Androstanes
Enones
Prodrugs
World Anti-Doping Agency prohibited substances