Testosterone propionate, sold under the brand name Testoviron 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 Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone as well as synthetic androgens that are structurally related and have similar effects t ...

(AAS) medication which is used mainly in the treatment of low testosterone levels in men. It has also been 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 ...

in women. It is given by

injection into muscle Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have l ...

usually once every two to three days.

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 testosterone propionate include

symptom Signs and symptoms are the observed or detectable signs, and experienced symptoms of an illness, injury, or condition. A sign for example may be a higher or lower temperature than normal, raised or lowered blood pressure or an abnormality showi ...

s 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, 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 ...

. The drug is a

synthetic Synthetic things are composed of multiple parts, often with the implication that they are artificial. In particular, 'synthetic' may refer to: Science * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic o ...

androgen and anabolic steroid and hence is an

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

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 characteris ...

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 incl ...

(DHT). It has strong

ic effects and 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-d ...

effects, which make it useful for producing masculinization and suitable for

androgen replacement therapy Androgen replacement therapy (ART), often referred to as testosterone replacement therapy (TRT) or hormone replacement therapy (HRT), is a form of hormone therapy in which androgens, often testosterone, are supplemented or replaced exogenousl ...

. Testosterone propionate is a testosterone ester and a relatively short-acting prodrug of

in the body. Because of this, it is considered to be a natural and bioidentical form of testosterone. Testosterone propionate was discovered in 1936 and was introduced for medical use in 1937. It was the first testosterone ester to be marketed, and was the major form of testosterone used in medicine until about 1960. The introduction of longer-acting testosterone esters like testosterone enanthate, testosterone cypionate, and

testosterone undecanoate Testosterone undecanoate, sold under the brand names Andriol and Aveed among others, is an androgen and anabolic steroid (AAS) medication that is used mainly in the treatment of low testosterone levels in men, including hormone therapy for tr ...

starting in the 1950s resulted in testosterone propionate mostly being superseded. As such, it is rarely used today. In addition to its medical use, testosterone 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 Sing ...

in many countries and so non-medical use is generally illicit.

Medical uses

Testosterone propionate is used primarily in

. It is specifically approved for the treatment of

hypogonadism Hypogonadism means diminished functional activity of the gonads—the testes or the ovaries—that may result in diminished production of sex hormones. Low androgen (e.g., testosterone) levels are referred to as hypoandrogenism and low est ...

in men,

, low sexual desire,

delayed puberty Delayed puberty is when a person lacks or has incomplete development of specific sexual characteristics past the usual age of onset of puberty. The person may have no physical or hormonal signs that puberty has begun. In the United States, girls ar ...

in boys, and menopausal

Available forms

Testosterone propionate is usually provided as an

oil solution An oil is any nonpolar chemical substance A chemical substance is a form of matter having constant chemical composition and characteristic properties. Some references add that chemical substance cannot be separated into its constituent C ...

for use by intramuscular injection. It was also previously available as an 30 mg or 50 mg

aqueous suspension In chemistry, a suspension is a heterogeneous mixture of a fluid that contains solid particles sufficiently large for sedimentation. The particles may be visible to the naked eye, usually must be larger than one micrometer, and will eventually s ...

. Buccal tablets of testosterone propionate were previously available as well.

Side effects

s of testosterone propionate include

virilization Virilization or masculinization is the biological development of adult male characteristics in young males or females. Most of the changes of virilization are produced by androgens. Virilization is most commonly used in three medical and biology ...

among others. Testosterone propionate is often a painful injection, which is attributed to its short ester chain.

Pharmacology

Pharmacodynamics

Testosterone propionate is a prodrug of testosterone and is an androgen and

anabolic–androgenic steroid Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone as well as synthetic androgens that are structurally related and have similar effects ...

(AAS). That is, it is an

of the androgen receptor (AR).

Pharmacokinetics

Testosterone propionate is administered in oil via

intramuscular injection Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have ...

. It has a relatively short

elimination half-life Biological half-life (also known as elimination half-life, pharmacologic half-life) is the time taken for concentration of a biological substance (such as a medication) to decrease from its maximum concentration ( Cmax) to half of Cmax in the bl ...

and mean residence time of 2 days and 4 days, respectively. As such, it has a short

duration of action Pharmacodynamics (PD) is the study of the biochemical and physiology, physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or combinations of o ...

and must be administered two to three times per week. Intramuscular injection of testosterone propionate as an

, and

emulsion An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althou ...

has been compared.

Chemistry

Testosterone propionate, or testosterone 17β-propanoate, is a

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 Pharmacolo ...

steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and ...

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. ...

. It 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-res ...

; specifically, it is the C17β propionate (propanoate)

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 ...

of testosterone.

History

Testosterone esters were synthesized for the first time in 1936, and were found to have greatly improved potency relative to testosterone. Among the esters synthesized, testosterone propionate was the most potent, and for this reason, was selected for further development, subsequently being marketed. Testosterone propionate was introduced in 1937 by Schering AG in

Germany Germany, officially the Federal Republic of Germany (FRG),, is a country in Central Europe. It is the most populous member state of the European Union. Germany lies between the Baltic and North Sea to the north and the Alps to the sou ...

under the brand name Testoviron. It was the first commercially available form of testosterone, and the first testosterone ester, to be introduced. The medication was the major form of testosterone used medically before 1960. Buccal testosterone propionate tablets were introduced for medical use in the mid-to-late 1940s under the brand name Oreton Buccal Tablets. An

of testosterone propionate was marketed by Ciba by 1950. In the 1950s, longer-acting testosterone esters like testosterone enanthate and testosterone cypionate were introduced and superseded testosterone propionate. Although rarely used nowadays due to its short duration, testosterone propionate remains medically available.

Society and culture

Generic names

''Testosterone propionate'' is the generic name of the drug and its and . It has also been referred to as ''testosterone propanoate'' or as ''propionyltestosterone''.

Brand names

Testosterone propionate is or has been marketed under a variety of brand names, including, among numerous others: * Agrovirin * Andronate * Andrusol-P * Anertan * Masenate * Neo-Hombreol * Oreton * Perandren * Synandrol * Testoviron

Availability

Testosterone propionate is no longer available commercially 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 U.S. state, states, a Washington, D.C., federal district, five ma ...

except via a compounding pharmacy.

Legal status

Testosterone propionate, along with other AAS, is a schedule III

in the

under the

Controlled Substances Act The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States ...

and a schedule IV controlled substance in

Canada Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by tota ...

under the

Controlled Drugs and Substances Act The ''Controlled Drugs and Substances Act'' (french: Loi réglementant certaines drogues et autres substances) (the ''Act'') is Canada's federal drug control statute. Passed in 1996 under Prime Minister Jean Chrétien's government, it repeals ...

References

{{Estrogen receptor modulators Androgens and anabolic steroids Androstanes Ketones Propionate esters Testosterone esters