Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, 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 was used to treat

breast cancer Breast cancer is cancer that develops from breast tissue. Signs of breast cancer may include a lump in the breast, a change in breast shape, dimpling of the skin, milk rejection, fluid coming from the nipple, a newly inverted nipple, or a r ...

in women but is now no longer marketed.https://www.drugs.com/international/dromostanolone.html 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 drostanolone propionate 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 ...

. It has no 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 ...

. 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

ic effects, which give it a mild side effect profile and make it especially suitable for use in women. The drug has 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. Drostanolone propionate is an

androgen ester An androgen or anabolic steroid ester is an ester of an androgen/anabolic steroid (AAS) such as the natural testosterone or dihydrotestosterone (DHT) or the synthetic nandrolone (19-nortestosterone). Esterification renders AAS into metabolism-re ...

and a long-lasting prodrug of

drostanolone Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. An androgen ester prodrug of drostanolone, drostanolone propionate, was formerly used in the treatment ...

in the body. Drostanolone propionate was first described in 1959 and was introduced for medical use in 1961. In addition to its medical use, drostanolone propionate 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.

Medical uses

The principal clinical indication of drostanolone propionate in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

as well as international markets was the treatment of advanced inoperable

in women.

Hormonal treatment Hormone therapy or hormonal therapy is the use of hormones in medical treatment. Treatment with hormone antagonists may also be referred to as hormonal therapy or antihormone therapy. The most general classes of hormone therapy are oncologic ho ...

is part of the complex therapy for some kind of

tumors A neoplasm () is a type of abnormal and excessive growth of tissue. The process that occurs to form or produce a neoplasm is called neoplasia. The growth of a neoplasm is uncoordinated with that of the normal surrounding tissue, and persists ...

, particularly the ones associated with hormone-active tissues like breast or prostate cancer. Some types of

cells, expressing

estrogen receptor Estrogen receptors (ERs) are a group of proteins found inside cells. They are receptors that are activated by the hormone estrogen (17β-estradiol). Two classes of ER exist: nuclear estrogen receptors ( ERα and ERβ), which are members of the ...

s (called ER+ cancers), use

for their growth and dissemination. That is why drugs that block estrogen receptors or decrease their expression on the cell membrane,

antiestrogen Antiestrogens, also known as estrogen antagonists or estrogen blockers, are a class of drugs which prevent estrogens like estradiol from mediating their biological effects in the body. They act by blocking the estrogen receptor (ER) and/or ...

s, could limit the tumor spread and size. Drostanolone propionate has been FDA approved as an

ic drug for the treatment of breast cancer. By the time of its release, there were not many alternatives for patients with breast cancer and drostanolone propionate was a revolution for these patients. As it has lower

ic rate compared to testosterone (medication), testosterone, the risk of virilization is much lighter. Due to this fact, women, who usually do not respond well to any AAS, were having much greater chance to survive cancer. Drostanolone propionate can also be used for breast tumors that do not respond well to other treatments or also as palliative care for advanced incurable tumors. The effects of the product depend of course on the dose and period of administration. The risk of virilization becomes greater with high doses and continuous administration period.

Non-medical uses

Drostanolone propionate is or has been used for performance-enhancing drug, physique- and performance-enhancing purposes by competition, competitive athletes, bodybuilders, and powerlifters.

Side effects

Drostanolone propionate produces considerably less virilization in women compared to equal doses of testosterone propionate. However, since the given dosage for breast cancer was relatively high (200 mg/twice a week), mild virilization including oily skin,

, voice deepening, hirsutism, and clitoromegaly, clitoral enlargement could still occur, and marked virilization could manifest with long-term therapy. The drug has no

ic activity and hence has no propensity for causing gynecomastia (in males) or water retention (medicine), fluid retention. Drostanolone propionate is not known to pose a risk of hepatotoxicity.

Pharmacology

Pharmacodynamics

Drostanolone propionate is a prodrug of

. Like other AAS, drostanolone is an agonist of the androgen receptor (AR). It is not a substrate for 5α-reductase and is a poor substrate for 3α-hydroxysteroid dehydrogenase (3α-HSD), and therefore shows a high ratio of

to androgenic activity. As a DHT derivative, drostanolone is not a substrate (biochemistry), substrate for aromatase and hence cannot be aromatized into

ic metabolites. While no data are available on the progestogenic activity of drostanolone, it is thought to have low or no such activity similarly to other DHT derivatives. Since the drug is not 17α-alkylated anabolic steroid, 17α-alkylated, it is not known to cause hepatotoxicity. Drostanolone propionate, via its active form drostanolone, interacts with the AR and activates a cascade of genetic changes, including increased protein synthesis (anabolism) and decreased amino acid metabolism, degradation (catabolism). It also induces a reduction or inhibition of prolactin inhibiting factor, prolactin or

s in the breasts, which is linked to its antitumor effects.

Pharmacokinetics

Drostanolone propionate is not active via the oral administration, oral route and must be administered via intramuscular injection. The elimination half-life of the drug via this route is approximately 2 days. It has a much longer elimination half-life via intramuscular injection than drostanolone. Drostanolone propionate is metabolism, metabolized into drostanolone, which is the active form.

Chemistry

Drostanolone propionate, or drostanolone 17β-propionate, is a synthetic androstane steroid and a chemical derivative, derivative of DHT. It is the C17β propionate (propanoate) ester of

, which itself is 2α-methyl-4,5α-dihydrotestosterone (2α-methyl-DHT) or 2α-methyl-5α-androstan-17β-ol-3-one.

History

Drostanolone and drostanolone propionate were first described in 1959. The related AAS oxymetholone and methasterone (methyldrostanolone) were first described in the same paper as well. Drostanolone propionate was introduced for medical use in the

in 1961 and in Europe shortly thereafter.

Society and culture

Generic names

''Drostanolone propionate'' is the generic term, generic name of the drug and its , while ''dromostanolone propionate'' is the and ; there is no for this form. The generic name of the unesterified form of the drug is ''drostanolone'' or ''dromostanolone'' and the former is its , , and while there is no .

Brand names

Drostanolone propionate was marketed under a variety of brand names including Drolban, Masterid, Masteril, Masteron, Masterone, Mastisol, Metormon, Permastril, and Prometholone.

Availability

Drostanolone propionate appears to no longer be marketed. It was previously available in the

, Europe, and Japan. In Europe, it was specifically marketed in the United Kingdom, Germany, Belgium, France, Spain, Portugal, Italy, and Bulgaria.

Legal status

Drostanolone propionate, along with other AAS, is a Controlled Substances Act#Schedule III controlled substances, schedule III

in the

under the Controlled Substances Act.

References

External links

{{Androgen receptor modulators Androgen esters Androgens and anabolic steroids Androstanes Bodybuilding Hormonal antineoplastic drugs Ketones Prodrugs Propionate esters World Anti-Doping Agency prohibited substances