Testosterone cypionate, sold under the brand name Depo-Testosterone 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 used mainly in the treatment of low testosterone levels in men, including

hormone therapy 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 hormonal therap ...

for

transgender men A trans man or transgender man is a man who was assigned female at birth. Trans men have a male gender identity, and many trans men undergo medical and social transition to alter their appearance in a way that aligns with their gender identi ...

. It is given by injection into muscle or

subcutaneously The subcutaneous tissue (), also called the hypodermis, hypoderm (), subcutis, or superficial fascia, is the lowermost layer of the integumentary system in vertebrates. The types of cells found in the layer are fibroblasts, adipose cells, and m ...

, once every one to four weeks, depending on clinical indication.

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 testosterone cypionate 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 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 a medical term commonly used in three medical a ...

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 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 ...

. Testosterone supplementation is also known to reduce the threshold for

aggressive behavior Aggression is behavior aimed at opposing or attacking something or someone. Though often done with the intent to cause harm, some might channel it into creative and practical outlets. It may occur either reactively or without provocation. In h ...

in men. The drug is a

synthetic Synthetic may refer to: Science * Synthetic biology * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic elements, chemical elements that are not naturally found on Earth and therefore have to be created in ...

androgen and anabolic steroid and hence 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 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). Testosterone cypionate is converted by the body to testosterone that has both

ic effects and

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 ...

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), is a form of hormone therapy in which androgens, often testosterone, are supplemented or replaced. It typically involves the administration of tes ...

; still, the relative potency of these effects can depend on various factors and is a topic of ongoing research. Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into DHT or aromatized to estradiol (E2). Both testosterone and DHT bind to an androgen receptor; however, DHT has a stronger binding affinity than testosterone and may have more androgenic effect in certain tissues at lower levels. Testosterone cypionate is a

testosterone 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 ...

and a long-lasting

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 ...

in the body. Because of this, it is considered to be a natural and bioidentical form of testosterone. Testosterone cypionate was introduced for medical use in 1951. Along with

testosterone enanthate Testosterone enanthate is used in the treatment of low testosterone levels in men. It is also used in hormone therapy for women and transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks. ...

testosterone undecanoate Testosterone undecanoate, sold under the brand name Nebido among others, is an androgen and anabolic steroid (AAS) medication that is used mainly in the treatment of low testosterone levels in men, It is taken by mouth or given by injection ...

, and

testosterone propionate Testosterone propionate, sold under the brand name Testoviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It has also been used to treat breast cance ...

, it is one of the most commonly used testosterone esters. It is used mainly 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 ...

. In addition to its medical use, testosterone cypionate 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 cypionate is used primarily in

. It is currently FDA approved for the treatment of primary or hypogonadotropic

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 ...

(either congenital or acquired). The drug's safety in andropause (

late-onset hypogonadism Late-onset hypogonadism (LOH) or testosterone deficiency syndrome (TDS) is a condition in older men characterized by measurably low testosterone levels and clinical symptoms mostly of a sexual nature, including decreased desire for mating, fewer s ...

in men) has not yet been established, and there are concerns that it may escalate the risks of

benign prostatic hyperplasia Benign prostatic hyperplasia (BPH), also called prostate enlargement, is a noncancerous increase in size of the prostate gland. Symptoms may include frequent urination, trouble starting to urinate, weak stream, urinary retention, inability t ...

prostate cancer Prostate cancer is the neoplasm, uncontrolled growth of cells in the prostate, a gland in the male reproductive system below the bladder. Abnormal growth of the prostate tissue is usually detected through Screening (medicine), screening tests, ...

and heart diseases. It is currently used off-label for

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 ...

breast disorder Breast diseases make up a number of conditions. The most common symptoms are a breast mass, breast pain, and nipple discharge. A majority of breast diseases are noncancerous. Although breast disease may be benign, or non-life threatening there ...

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 hormone, hormonal signs that puberty has begun. In the United States ...

in boys,

oligospermia Terms oligospermia, oligozoospermia, and low sperm count refer to semen with a low concentration of sperm and is a common finding in male infertility. Often, semen with a decreased sperm concentration may also show significant abnormalities in sper ...

(low sperm count), transmasculine hormone replacement therapy in

transgender A transgender (often shortened to trans) person has a gender identity different from that typically associated with the sex they were sex assignment, assigned at birth. The opposite of ''transgender'' is ''cisgender'', which describes perso ...

men, and

osteoporosis Osteoporosis is a systemic skeletal disorder characterized by low bone mass, micro-architectural deterioration of bone tissue leading to more porous bone, and consequent increase in Bone fracture, fracture risk. It is the most common reason f ...

Side effects

s of testosterone cypionate 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 a medical term commonly used in three medical a ...

among others. Diminished sperm production is a common side-effect of testosterone replacement therapy because of the decreased intra-testicular concentration of testosterone and suppression of the hypothalamic-pituitary-gonadal axis.

Pharmacology

Pharmacodynamics

Testosterone cypionate is a

of testosterone and is an androgen and

anabolic–androgenic 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). That is, it is an

of the

(AR). Testosterone cypionate is converted by the body to testosterone that has both

ic effects and

effects; still, the relative potency of these effects can depend on various factors and is a topic of ongoing research. Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into dihydrotestosterone (DHT) or aromatized to estradiol (E2). Both testosterone and DHT bind to an androgen receptor; however, DHT has a stronger binding affinity than testosterone and may have more androgenic effect in certain tissues at lower levels.

Pharmacokinetics

The

pharmacokinetics Pharmacokinetics (from Ancient Greek ''pharmakon'' "drug" and ''kinetikos'' "moving, putting in motion"; see chemical kinetics), sometimes abbreviated as PK, is a branch of pharmacology dedicated to describing how the body affects a specific su ...

of testosterone cypionate via depot

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

, including its

elimination half-life Biological half-life (elimination half-life, pharmacological 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 blood plasma. ...

and

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

, are said to be extremely comparable to and hence essentially the same as those of

. As such, testosterone cypionate and testosterone enanthate are considered to be "functionally interchangeable" as medications. For reference, testosterone enanthate has an elimination half-life of 4.5 days and a mean residence time of 8.5 days and requires frequent administration of approximately once per week. Large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological. The pharmacokinetics of testosterone cypionate have been studied and reported.

Chemistry

Testosterone cypionate, or testosterone 17β-cyclopentylpropionate, 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 Pharmacolog ...

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 ...

. 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 cyclopentylpropionate (cypionate)

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

of testosterone.

History

Testosterone cypionate was first synthesized in 1951 and was introduced for medical use in the

the same year under the brand name Depo-Testosterone.

Society and culture

Generic names

''Testosterone cypionate'' is the generic name of the drug and its .

Brand names

Testosterone cypionate is or has been marketed under a variety of brand names, including: * Andro Cyp * Andronaq LA * Andronate * Dep Andro * Dep Test * Deposteron * Depostomead * Depotest * Depo-Testosterone * Depovirin * Durandro * Duratest * Jectatest * Malogen CYP * Pertestis * Testa-C * Testadiate Depo * Testex Elmu Prolongatum * Testoject LA * Virilon

Availability

Testosterone cypionate is marketed in the

. It is not widely available outside of the United States, though it has been marketed in

Canada Canada is a country in North America. Its Provinces and territories of Canada, ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, making it the world's List of coun ...

Australia Australia, officially the Commonwealth of Australia, is a country comprising mainland Australia, the mainland of the Australia (continent), Australian continent, the island of Tasmania and list of islands of Australia, numerous smaller isl ...

Spain Spain, or the Kingdom of Spain, is a country in Southern Europe, Southern and Western Europe with territories in North Africa. Featuring the Punta de Tarifa, southernmost point of continental Europe, it is the largest country in Southern Eur ...

Brazil Brazil, officially the Federative Republic of Brazil, is the largest country in South America. It is the world's List of countries and dependencies by area, fifth-largest country by area and the List of countries and dependencies by population ...

, and

South Africa South Africa, officially the Republic of South Africa (RSA), is the Southern Africa, southernmost country in Africa. Its Provinces of South Africa, nine provinces are bounded to the south by of coastline that stretches along the Atlantic O ...

Legal status

Testosterone cypionate, 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 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 ...

and a schedule IV controlled substance in

under the

Controlled Drugs and Substances Act Control may refer to: Basic meanings Economics and business * Control (management), an element of management * Control, an element of management accounting * Comptroller (or controller), a senior financial officer in an organization * Controll ...

References

{{Estrogen receptor modulators Anabolic–androgenic steroids Androstanes Cypionate esters Ketones Testosterone esters