Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the

dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production o ...

(DHT) group which was never marketed. An androgen ester

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

of drostanolone, drostanolone propionate, was formerly used in the treatment of

breast cancer Breast cancer is a cancer that develops from breast tissue. Signs of breast cancer may include a Breast lump, lump in the breast, a change in breast shape, dimpling of the skin, Milk-rejection sign, milk rejection, fluid coming from the nipp ...

in women under brand names such as Drolban, Masteril, and Masteron. This has also been used non-medically for physique- or performance-enhancing purposes.

Pharmacology

Pharmacodynamics

Like other AAS, drostanolone 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). 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

anabolic Anabolism () is the set of metabolic pathways that construct macromolecules like DNA or RNA from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catab ...

to androgenic activity. As a DHT derivative, drostanolone is not a substrate for

aromatase Aromatase (), also called estrogen synthetase or estrogen synthase, is an enzyme responsible for a key step in the biosynthesis of estrogens. It is CYP19A1, a member of the cytochrome P450 superfamily, which are monooxygenases that catalyze man ...

and hence cannot be aromatized into

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 ...

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. 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, it is not known to cause

hepatotoxicity Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdr ...

Chemistry

Drostanolone, also known as 2α-methyl-5α-dihydrotestosterone (2α-methyl-DHT) or as 2α-methyl-5α-androstan-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

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 DHT. It is specifically DHT with a

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...

at the C2α position.

History

Drostanolone and its ester drostanolone propionate were first described in 1959. Drostanolone propionate was first introduced for medical use in 1961.

Society and culture

Generic names

''Drostanolone'' is the generic name of the drug and its , , and . It has also been referred to as ''dromostanolone''.

Legal status

Drostanolone, along with other AAS, is a schedule III controlled substance in 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 ...

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 ...

Potential side effects

Like other AAS, drostanolone can cause a variety of side effects, including: * Virilization: This refers to the development of masculine characteristics in women, such as deepening of the voice, increased body hair growth, and clitoral enlargement. * Acne: AAS can increase sebum production, leading to acne. * Hair loss: Drostanolone can accelerate male pattern baldness. * Cardiovascular issues: AAS can negatively affect cholesterol levels and increase the risk of cardiovascular disease. * Liver damage: Although drostanolone is not 17α-alkylated, high doses or prolonged use can still potentially damage the liver. * Mood swings: AAS can cause aggression, irritability, and mood swings.

Non-medical uses

''Drostanolone'' is used by some bodybuilders and athletes to increase muscle mass and strength. It is often used during "cutting cycles" to help preserve muscle mass while losing body fat. However, the use of AAS for non-medical purposes is not recommended due to the potential for serious side effects.

Synthesis

Bolazine is when react 2 eq. with hydrazine to give dimer Drostanolone synthesis

Treatment of DHT (androstan-17β-ol-3-one, stanolone) 21-18-6(1) with methyl formate and the strong base sodium methoxide gives 033-95-8(2). The newly added formyl function in the product is shown in the enol form. Catalytic hydrogenation reduces that function to a methyl group (3). The addition of hydrogen from the bottom face of the molecule leads to the formation of β-methyl isomer where the methyl group occupies the higher-energy axial position. Strong base-induced equilibration of the methyl group leads to the formation of the sterically favoured equatorial α-methyl isomer, affording dromostanolone (4).

References

External links

Masteron (drostanolone propionate) - William Llewellyn's Anabolic.org
{{Androgen receptor modulators Cyclopentanols Anabolic–androgenic steroids Androstanes Ketones