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
CompTox Dashboard (EPA)
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 women [6] and transsexual men [ medical citation needed ]. 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] Esterase enzymes break the ester bond in testosterone enantate, releasing free testosterone and enanthic acid through hydrolysis. [10] [11] [12] This process ensures a sustained release of testosterone in the body. [13]

Testosterone enanthate was introduced for medical use in 1954. [14] [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] [15] 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. [16] 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 5α-dihydrotestosterone in normal men. [17] 5α-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. [18] [19] Testosterone enanthate can also be converted to estradiol (E2) by the aromatase enzyme, [20] which may lead to gynecomastia in males. Aromatase inhibitors, such as anastrozole, letrozole, exemestane, etc., can help to prevent the subsequent estrogenic activity of testosterone enanthate metabolites in the body. [20]

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 enanthate 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. [21] [22] Esterase enzymes break the ester bond in testosterone enantate, releasing free testosterone and enanthic acid through hydrolysis. This process ensures a sustained release of free bioavailable and bioactive testosterone in the body. Testosterone can either directly exert effects on target tissues or be metabolized by the 5α-reductase enzymes into 5α-dihydrotestosterone (DHT) or aromatized to estradiol (E2). [21] Aromatization in this context is the process where testosterone is converted to estradiol (E2) by the enzyme aromatase (CYP19A1 in humans). This conversion involves changing the structure of testosterone to include an aromatic ring A of a steroid nucleus, making it an estrogen, a so-called female hormone, which plays various roles in the body, such as regulating reproductive functions and bone density. If not aromatized (not converted into an estrogen), both testosterone and DHT are bioactive and bind to an androgen receptor; however, DHT has a stronger binding affinity than testosterone and may have more androgenic effect in certain tissues (such as prostate gland, skin and hair follicles) [23] at lower levels. [21]

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] When testosterone enanthate is dissolved in an oil (such as castor oil), the oil acts as a depot, or reservoir, that slowly releases the drug into the bloodstream. This slow release is due to the oil's viscosity and the gradual breakdown of the ester bond by esterase enzymes. The oil creates a barrier that slows the diffusion of testosterone enanthate into the surrounding tissues, resulting in a more controlled and prolonged release compared to injecting pure testosterone enanthate. [24] [25] The rate at which testosterone enanthate is released from oils can vary based on the oil's viscosity and other properties such as drug solubility in the oil. [26] [27] [28] [29]

Chemistry

Testosterone enanthate, or testosterone 17β-heptanoate, is a synthetic androstane steroid and a derivative of testosterone. [30] [31] It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone. [30] [31]

History

Testosterone enanthate was described as early as 1952 [32] and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl. [14] [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. [30] [31] [33] [34] It has also referred to as testosterone heptanoate. [30] [31] [33] [34]

Brand names

Testosterone enanthate is marketed primarily under the brand name Delatestryl. [30] [31] [33] [34]

It is or has been marketed under a variety of other brand names as well, including, among others: [30] [31] [33] [34] [35]

Availability

Testosterone enanthate is available in the United States and widely elsewhere throughout the world. [36] [31] [34] Testosterone enanthate (testosterone heptanoate) is often available in concentrations of 200 mg per milliliter of fluid. [37]

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. [38] [39]

Research

As of October 2017, an auto-injection formulation of testosterone enanthate was in preregistration for the treatment of hypogonadism in the United States. [40]

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. [41]

Related Research Articles

<span class="mw-page-title-main">Dihydrotestosterone</span> Human hormone

Dihydrotestosterone 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 of sebum and body hair composition.

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

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen. 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 now used by oral administration or 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 names Rolon and Deca-Durabolin, 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">Trenbolone</span> Anabolic steroid

Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed. Trenbolone ester prodrugs, including trenbolone acetate and trenbolone hexahydrobenzylcarbonate, are or have been marketed for veterinary and clinical use. Trenbolone acetate is used in veterinary medicine in livestock to increase muscle growth and appetite, while trenbolone hexahydrobenzylcarbonate was formerly used clinically in humans but is now no longer marketed. In addition, although it is not approved for clinical or veterinary use, trenbolone enanthate is sometimes sold on the black market under the nickname Trenabol.

<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, including 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">Trestolone</span> Chemical compound

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

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

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

<span class="mw-page-title-main">Anabolic steroid</span> Class of drugs

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). 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 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 into muscle.

<span class="mw-page-title-main">Androstanolone enanthate</span> Synthetic androgen and anabolic steroid

Androstanolone enanthate, also known as stanolone enanthate or dihydrotestosterone heptanoate (DHTH), as well as 5α-androstan-17β-ol-3-one 17β-heptanoate, is a synthetic androgen and anabolic steroid and a dihydrotestosterone ester. It is used as an injectable and acts as a prodrug of androstanolone. The drug has been studied in and found to be effective in the treatment of gynecomastia in boys and adult men. The pharmacology of androstanolone enanthate has been studied.

<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 transdermal patch that is applied to the skin topically, intramuscular injection (IM), buccally, or as an oral tablet.

<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.

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