Testosterone enanthate

Last updated
Testosterone enanthate
Testosterone enanthate.svg
Testosterone enanthate molecule ball.png
Clinical data
Trade names Delatestryl, Xyosted, others
Other namesTE; Testosterone heptanoate; Testosterone 17β-heptanoate; NSC-17591
Routes of
administration 		Intramuscular injection, subcutaneous injection
Drug class Androgen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
Bioavailability Oral: very low
Intramuscular: high
Metabolism Liver
Elimination half-life Intramuscular: 4–5 days [2]
Excretion Urine
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] heptanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.005.686 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C26H40O3
Molar mass 400.603 g·mol−1
3D model (JSmol)
  • CCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
  • InChI=1S/C26H40O3/c1-4-5-6-7-8-24(28)29-23-12-11-21-20-10-9-18-17-19(27)13-15-25(18,2)22(20)14-16-26(21,23)3/h17,20-23H,4-16H2,1-3H3/t20-,21-,22-,23-,25-,26-/m0/s1
  • Key:VOCBWIIFXDYGNZ-IXKNJLPQSA-N

Testosterone enanthate is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. [3] [4] [5] It is also used in hormone therapy for transgender men. [6] It is given by injection into muscle or subcutaneously usually once every one to four weeks. [5] [7] [2]

Contents

Side effects of testosterone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [5] 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). [8] [5] Testosterone enanthate is a testosterone ester and a long-lasting prodrug of testosterone in the body. [7] [3] [4] Because of this, it is considered to be a natural and bioidentical form of testosterone, [9] which make it useful for producing masculinization and suitable for androgen replacement therapy. [5]

Testosterone enanthate was introduced for medical use in 1954. [10] [4] Along with testosterone cypionate, testosterone undecanoate, and testosterone propionate, it is one of the most widely used testosterone esters. [8] [4] [5] In addition to its medical use, testosterone enanthate is used to improve physique and performance. [5] The drug is a controlled substance in many countries and so non-medical use is generally illicit. [5]

Medical uses

Testosterone enanthate is used primarily in androgen replacement therapy. [4] [11] It is the most widely used form of testosterone in androgen replacement therapy. [4] The medication is specifically approved, in the United States, for the treatment of hypogonadism in men, delayed puberty in boys, and breast cancer in women. [12] It is also used in masculinizing hormone therapy for transgender men. [6]

Side effects

Side effects of testosterone enanthate include virilization among others. [5] Approximately 10 percent of testosterone enanthate will be converted to dihydrotestosterone in normal men. [13] Dihydrotestosterone (DHT) can promote masculine characteristics in both males and females. These masculine characteristics include: clitoral hypertrophy, androgenic alopecia, growth of body hair and deepening of the vocal cords. Dihydrotestosterone also plays an important role in male sexual function and may also be a contributing factor of ischemic priapism in males as shown in a study conducted on the use of finasteride to treat ischemic priapism in males. Testosterone enanthate can also lead to an increase in IGF-1 and IGFBP. [14] [15] Testosterone enanthate can also be converted to estradiol by aromatase, [16] which may lead to gynecomastia in males. Aromatase inhibitors can help to prevent the estrogenic activity of testosterone enanthate in the body. [16]

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 enanthate 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; [5] still, the relative potency of these effects can depend on various factors and is a topic of ongoing research. [17] [18] Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into dihydrotestosterone (DHT) or aromatized to estradiol (E2). [17] 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. [17]

Pharmacokinetics

Testosterone enanthate has an elimination half-life of 4.5 days and a mean residence time of 8.5 days when used as a depot intramuscular injection. [2] It requires frequent administration of approximately once per week, and large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological. [2]

Chemistry

Testosterone enanthate, or testosterone 17β-heptanoate, is a synthetic androstane steroid and a derivative of testosterone. [19] [20] It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone. [19] [20]

History

Testosterone enanthate was described as early as 1952 [21] and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl. [10] [4]

Society and culture

Generic names

Testosterone enanthate is the generic name of the drug and its USAN Tooltip United States Adopted Name and BAN Tooltip British Approved Name. [19] [20] [22] [23] It has also referred to as testosterone heptanoate. [19] [20] [22] [23]

Brand names

Testosterone enanthate is marketed primarily under the brand name Delatestryl. [19] [20] [22] [23]

It is or has been marketed under a variety of other brand names as well, including, among others: [19] [20] [22] [23] [24]

Availability

Testosterone enanthate is available in the United States and widely elsewhere throughout the world. [25] [20] [23] Testosterone enanthate (testosterone heptanoate) is often available in concentrations of 200 mg per milliliter of fluid. [26]

Testosterone enanthate, 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. [27] [28]

Research

As of October 2017, an auto-injection formulation of testosterone enanthate was in preregistration for the treatment of hypogonadism in the United States. [29]

Xyosted

On October 1, 2018, the U.S. Food and Drug Administration (FDA) announced the approval of Xyosted. Xyosted, a product of Antares Pharma, Inc., is a single-use disposable auto-injector that dispenses testosterone enanthate. Xyosted is the first FDA-approved subcutaneous testosterone enanthate product for testosterone replacement therapy in adult males. [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">Oxandrolone</span> Androgen and anabolic steroid

Oxandrolone is an androgen and synthetic anabolic steroid (AAS) medication to help promote weight gain in various situations, to help offset protein catabolism caused by long-term corticosteroid therapy, to support recovery from severe burns, to treat bone pain associated with osteoporosis, to aid in the development of girls with Turner syndrome, and for other indications. It is taken by mouth. It was sold under the brand names Oxandrin and Anavar, among others.

<span class="mw-page-title-main">Oxymetholone</span> Androgen and anabolic steroid

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemia. It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain and muscle growth in certain situations. It is taken by mouth.

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

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. It is also used in hormone therapy for transgender men. It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication.

<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">Androgen ester</span> Class of chemical compounds

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-resistant prohormones of themselves, improving oral bioavailability, increasing lipophilicity, and extending the elimination half-life. In addition, with intramuscular injection, AAS esters are absorbed more slowly into the body, further improving the elimination half-life. Aside from differences in pharmacokinetics, these esters essentially have the same effects as the parent drugs. They are used in androgen replacement therapy (ART), among other indications. Examples of androgen esters include testosterone esters such as testosterone cypionate, testosterone enanthate, testosterone propionate, and testosterone undecanoate and nandrolone esters such as nandrolone decanoate and nandrolone phenylpropionate.

<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 (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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