Testosterone cypionate

Last updated
Testosterone cypionate
Testosterone cypionate.svg
Testosterone cypionate molecule ball.png
Clinical data
Trade names Depo-Testosterone, others
Other namesTC; TCPP; Testosterone cipionate; Testosterone cyclopentylpropionate; Testosterone cyclopentanepropionate; Testosterone 17β-cyclopentylpropionate
Routes of
administration 		Intramuscular injection
Drug class Androgen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
Bioavailability Oral: very low
Intramuscular: very high
Metabolism Liver
Elimination half-life ~8 days i.m. Tooltip intramuscular injection) [1]
Excretion 90% Urine; 6% feces [1]
Identifiers
  • [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.000.335 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H40O3
Molar mass 412.614 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=CC(=O)CC[C@]35C
  • InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1
  • Key:HPFVBGJFAYZEBE-ZLQWOROUSA-N

Testosterone cypionate, sold under the brand name Depo-Testosterone among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. [2] [3] [4] It is also used in hormone therapy for transgender men. [5] [6] It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication. [4] [7] [8] [9]

Contents

Side effects of testosterone cypionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [4] Testosterone supplementation is also known to reduce the threshold for aggressive behavior in men. [10] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). [11] [4] Testosterone cypionate is converted by the body to testosterone that has both androgenic effects and anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy; [4] still, the relative potency of these effects can depend on various factors and is a topic of ongoing research. [12] [13] Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into DHT or aromatized to estradiol (E2). [12] 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. [12] Testosterone cypionate is a testosterone ester and a long-lasting prodrug of testosterone in the body. [7] [2] [3] Because of this, it is considered to be a natural and bioidentical form of testosterone. [14]

Testosterone cypionate was introduced for medical use in 1951. [15] [16] Along with testosterone enanthate, testosterone undecanoate, and testosterone propionate, it is one of the most commonly used testosterone esters. [11] [4] It is used mainly in the United States. [4] In addition to its medical use, testosterone cypionate is used to improve physique and performance. [4] The drug is a controlled substance in many countries and so non-medical use is generally illicit. [4]

Medical uses

Testosterone cypionate is used primarily in androgen replacement therapy. [17] It is currently FDA approved for the treatment of primary or hypogonadotropic hypogonadism (either congenital or acquired). The drug's safety in andropause (late-onset hypogonadism in men) has not yet been established, [1] and there are concerns that it may escalate the risks of benign prostatic hyperplasia, prostate cancer and heart diseases. [18] It is currently used off-label for breast cancer, breast disorders, delayed puberty in boys, oligospermia (low sperm count), transmasculine hormone replacement therapy in transgender men, [9] and osteoporosis. [19] [1]

Side effects

Side effects of testosterone cypionate include virilization among others. [4] It can also create conditions for heart attack, enlargement of prostate gland, liver malfunction, issues related to coagulation, pulmonary embolism, and polycythemia. [20] 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. [21]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
MedicationRatioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes:a = Ratio of androgenic to anabolic activity. Sources: See template.

Testosterone cypionate is a prodrug of testosterone and is an androgen and anabolic–androgenic steroid (AAS). That is, it is an agonist of the androgen receptor (AR).

Testosterone cypionate is converted by the body to testosterone that has both androgenic effects and anabolic effects; [4] still, the relative potency of these effects can depend on various factors and is a topic of ongoing research. [12] [13] Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into dihydrotestosterone (DHT) or aromatized to estradiol (E2). [12] 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. [12]

Pharmacokinetics

The pharmacokinetics of testosterone cypionate via depot intramuscular injection, including its elimination half-life and duration of action, are said to be extremely comparable to and hence essentially the same as those of testosterone enanthate. [4] [3] As such, testosterone cypionate and testosterone enanthate are considered to be "functionally interchangeable" as medications. [4] 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. [22] Large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological. [22] The pharmacokinetics of testosterone cypionate have been studied and reported. [23]

Chemistry

Testosterone cypionate, or testosterone 17β-cyclopentylpropionate, is a synthetic androstane steroid and a derivative of testosterone. [24] [25] It is an androgen ester; specifically, it is the C17β cyclopentylpropionate (cypionate) ester of testosterone. [24] [25]

History

Testosterone cypionate was first synthesized in 1951 [26] and was introduced for medical use in the United States the same year under the brand name Depo-Testosterone. [15] [16]

Society and culture

Generic names

Testosterone cypionate is the generic name of the drug and its USP Tooltip United States Pharmacopeia. [24] [25] [27] [28] The drug does not have an INN Tooltip International Nonproprietary Name, USAN Tooltip United States Adopted Name, or BAN Tooltip British Approved Name. [24] [25] [27] [28] It has also been referred to as testosterone cipionate, as well as testosterone cyclopentylpropionate or testosterone cyclopentanepropionate. [24] [25] [27] [28]

Brand names

Testosterone cypionate is or has been marketed under a variety of brand names, including: [24] [25] [27] [28]

Availability

Testosterone cypionate is marketed in the United States. [4] [25] It is not widely available outside of the United States, though it has been marketed in Canada, Australia, Spain, Brazil, and South Africa. [4] [25]

Testosterone cypionate, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act and a schedule IV controlled substance in Canada under the Controlled Drugs and Substances Act. [29] [30]

Related Research Articles

<span class="mw-page-title-main">Methyltestosterone</span> Chemical compound

Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. It is taken by mouth or held in the cheek or under the tongue.

<span class="mw-page-title-main">Nandrolone</span> Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

<span class="mw-page-title-main">Metenolone</span> Chemical compound

Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate and metenolone enanthate. Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure. Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.

<span class="mw-page-title-main">Nandrolone decanoate</span> Anabolic steroid

Nandrolone decanoate, sold under the brand name ROLON among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women. It is given by injection into muscle or fat once every one to four weeks.

<span class="mw-page-title-main">Testosterone enanthate</span> Chemical compound

Testosterone enanthate is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone therapy for transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.

<span class="mw-page-title-main">Testosterone propionate</span> Chemical compound

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 cancer in women. It is given by injection into muscle usually once every two to three days.

<span class="mw-page-title-main">Metenolone enanthate</span> Chemical compound

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. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

<span class="mw-page-title-main">Mesterolone</span> Chemical compound

Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. It has also been used to treat male infertility, although this use is controversial. It is taken by mouth.

<span class="mw-page-title-main">Fluoxymesterone</span> Chemical compound

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth.

<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

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. Anabolic steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance.

<span class="mw-page-title-main">Testosterone undecanoate</span> Chemical compound

Testosterone undecanoate, sold under the brand names Andriol, Aveed and 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 into muscle.

<span class="mw-page-title-main">Trenbolone enanthate</span> Chemical compound

Trenbolone enanthate, known by the nickname Trenabol, is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone which was never marketed. It is the C17β enanthate ester and a long-acting prodrug of trenbolone. Trenbolone enanthate was never approved for medical or veterinary use but is used in scientific research and has been sold on the internet black market as a designer steroid for bodybuilders and athletes.

<span class="mw-page-title-main">Nandrolone phenylpropionate</span> Anabolic steroid

Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporosis in women. It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.

<span class="mw-page-title-main">Testosterone buciclate</span> Chemical compound

Testosterone buciclate is a synthetic, injected anabolic–androgenic steroid (AAS) which was never marketed. It was developed in collaboration by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and the World Health Organization (WHO) in the 1970s and early 1980s for use in androgen replacement therapy for male hypogonadism and as a potential male contraceptive. It was first described in 1986. The medication is an androgen ester – specifically, the C17β buciclate (4-butylcyclohexane-1-carboxylate) ester of testosterone – and is a prodrug of testosterone with a very long duration of action when used as a depot via intramuscular injection. Testosterone buciclate is formulated as a microcrystalline aqueous suspension with a defined particle size of at least 75% in the range of 10 to 50 μm.

<span class="mw-page-title-main">Testosterone (medication)</span> Medication and naturally occurring steroid hormone

Testosterone (T) is a medication and naturally occurring steroid hormone. It is used to treat male hypogonadism, gender dysphoria, and certain types of breast cancer. It may also be used to increase athletic ability in the form of doping. It is unclear if the use of testosterone for low levels due to aging is beneficial or harmful. Testosterone can be used as a gel or patch that is applied to the skin, injection into a muscle, tablet that is placed in the cheek, or tablet that is taken by mouth.

<span class="mw-page-title-main">Metenolone acetate</span> Chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. 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, is given by injection into muscle.

<span class="mw-page-title-main">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

<span class="mw-page-title-main">Pharmacokinetics of testosterone</span>

The pharmacology of testosterone, an androgen and anabolic steroid (AAS) medication and naturally occurring steroid hormone, concerns its pharmacodynamics, pharmacokinetics, and various routes of administration.

References

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