testosterone enanthate

{{See also|Androgen replacement therapy#Medical uses|Anabolic steroid#Medical}}

Testosterone enanthate is used primarily in androgen replacement therapy.{{Cite news |title=Testosterone Enanthate raw powder (CAS 315-37-7) ≥98% {{!}} AASraw |language=en-US |work=aasraw |url=https://www.aasraw.com/products/testosterone-enanthate/ |access-date=2022-11-20 |archive-date=2022-11-20 |archive-url=https://web.archive.org/web/20221120110631/https://www.aasraw.com/products/testosterone-enanthate/ |url-status=live }} It is the most widely used form of testosterone in androgen replacement therapy. 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.{{cite web | title = DELATESTRYL Package Insert | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009165s031lbl.pdf | publisher = Indevus Pharmaceuticals, Inc. | access-date = 2017-12-11 | archive-date = 2017-02-16 | archive-url = https://web.archive.org/web/20170216165228/http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009165s031lbl.pdf | url-status = dead }} It is also used in masculinizing hormone therapy for transgender men.

{{See also|Anabolic steroid#Adverse effects|Androgen replacement therapy#Adverse effects}}

Side effects of testosterone enanthate include virilization among others. Approximately 10 percent of testosterone enanthate will be converted to 5α-dihydrotestosterone in normal men.{{Cite web| url=https://www.medicalnewstoday.com/articles/68082.php| title=DHT (dihydrotestosterone): What is DHT's role in baldness?| date=28 July 2017| access-date=9 May 2019| archive-date=8 October 2019| archive-url=https://web.archive.org/web/20191008160340/https://www.medicalnewstoday.com/articles/68082.php| url-status=live}} 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.{{cite journal | vauthors = Ashton WS, Degnan BM, Daniel A, Francis GL | title = Testosterone increases insulin-like growth factor-1 and insulin-like growth factor-binding protein | journal = Annals of Clinical and Laboratory Science | volume = 25 | issue = 5 | pages = 381–388 | date = 1995 | pmid = 7486812 }}{{cite journal | vauthors = Hoeh MP, Levine LA | title = Management of Recurrent Ischemic Priapism 2014: A Complex Condition with Devastating Consequences | journal = Sexual Medicine Reviews | volume = 3 | issue = 1 | pages = 24–35 | date = March 2015 | pmid = 27784569 | doi = 10.1002/smrj.37 | s2cid = 24028084 }} Testosterone enanthate can also be converted to estradiol (E2) by the aromatase enzyme,{{cite journal | vauthors = Ishikawa T, Glidewell-Kenney C, Jameson JL | title = Aromatase-independent testosterone conversion into estrogenic steroids is inhibited by a 5 alpha-reductase inhibitor | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 98 | issue = 2–3 | pages = 133–138 | date = February 2006 | pmid = 16386416 | doi = 10.1016/j.jsbmb.2005.09.004 | s2cid = 25849126 }} 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.

{{See also|Testosterone#Mechanism of action|Anabolic steroid#Pharmacology}}

{{Relative androgenic to anabolic activity in animals}}

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; still, the relative potency of these effects can depend on various factors and is a topic of ongoing research.{{cite book | chapter-url=https://link.springer.com/referenceworkentry/10.1007/978-3-319-29456-8_11-1 | doi=10.1007/978-3-319-29456-8_11-1 | chapter=Anabolic and Metabolic Effects of Testosterone and Other Androgens: Direct Effects and Role of Testosterone Metabolic Products | title=Thyroid Diseases | series=Endocrinology | date=2017 | vauthors = Čeponis J, Wang C, Swerdloff RS, Liu PY | pages=1–22 | isbn=978-3-319-29195-6 | access-date=2024-04-06 | archive-date=2024-04-07 | archive-url=https://web.archive.org/web/20240407084734/https://link.springer.com/referenceworkentry/10.1007/978-3-319-29456-8_11-1 | url-status=live }}{{cite journal |vauthors=Kuhn CM |title=Anabolic steroids |journal=Recent Prog Horm Res |volume=57 |issue= |pages=411–34 |date=2002 |pmid=12017555 |doi=10.1210/rp.57.1.411 |url=|doi-access=free }} 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). 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){{cite journal|doi=10.1210/er.2016-1067 |title=Dihydrotestosterone: Biochemistry, Physiology, and Clinical Implications of Elevated Blood Levels |date=2017 |journal=Endocrine Reviews |volume=38 |issue=3 |pages=220–254 |pmid=28472278 |pmc=6459338 | vauthors = Swerdloff RS, Dudley RE, Page ST, Wang C, Salameh WA }} at lower levels.

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. 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. 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.{{Cite web |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009165s031lbl.pdf |title=Archived copy |access-date=2017-12-11 |archive-date=2017-02-16 |archive-url=https://web.archive.org/web/20170216165228/http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009165s031lbl.pdf |url-status=dead }}{{cite web | url=https://go.drugbank.com/drugs/DB13944 | title=Testosterone enanthate | access-date=2024-11-06 | archive-date=2019-06-29 | archive-url=https://web.archive.org/web/20190629184318/https://www.drugbank.ca/drugs/DB13944 | url-status=live }} 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.{{Cite web |url=https://medicalhealthinstitute.com/best-oils-to-use-when-injecting-testosterone-therapy/ |title=Archived copy |access-date=2024-11-06 |archive-date=2024-05-23 |archive-url=https://web.archive.org/web/20240523181842/https://medicalhealthinstitute.com/best-oils-to-use-when-injecting-testosterone-therapy/ |url-status=live }}{{cite book | chapter-url=https://link.springer.com/chapter/10.1007/978-1-4614-0554-2_7 | doi=10.1007/978-1-4614-0554-2_7 | chapter=Oily (Lipophilic) Solutions and Suspensions | title=Long Acting Injections and Implants | date=2012 | pages=113–135 | isbn=978-1-4614-0553-5 | vauthors=Larsen SW, Thing MA, Larsen C | publisher=Springer | access-date=2024-11-06 | archive-date=2023-04-10 | archive-url=https://web.archive.org/web/20230410074347/https://link.springer.com/chapter/10.1007/978-1-4614-0554-2_7 | url-status=live }}{{cite journal | url=https://link.springer.com/article/10.1208/s12249-019-1454-4 | doi=10.1208/s12249-019-1454-4 | title=Investigation of Controlled Release Molecular Mechanism of Oil Phase in Spilanthol Emulsion: Development and in Vitro, in Vivo Characterization | date=2019 | journal=AAPS PharmSciTech | volume=20 | issue=6 | page=227 | pmid=31222590 | vauthors = Yang D, Li W, Fang L, Liu C | url-access=subscription }}https://www.jpharmsci.org/article/S0022-3549(15)38234-4/abstract

{{See also|Androgen ester|List of androgen esters}}

Testosterone enanthate, or testosterone 17β-heptanoate, is a synthetic androstane steroid and a derivative of testosterone.{{cite book| vauthors = Elks J |title= The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=641–642}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1002|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=1002–1004|access-date=2017-12-13|archive-date=2024-10-04|archive-url=https://web.archive.org/web/20241004183902/https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1002#v=onepage&q&f=false|url-status=live}} It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone.

Testosterone enanthate was described as early as 1952{{cite book |doi=10.1007/978-3-642-49902-9_11 |chapter=Über protrahiert wirksame Androgene |trans-chapter=Over protracted effective androgens |title=Festschrift zum 75. Geburtstag |pages=85–92 |year=1952 | vauthors = Junkmann K |publisher=Springer |isbn=978-3-642-49610-3 }} and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl.{{cite encyclopedia |url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PAPA3171 |title=Testosterone Enanthate |page=35t |doi=10.1016/B978-0-8155-1526-5.50024-6 |encyclopedia=Pharmaceutical Manufacturing Encyclopedia |volume=T |year=2007 |publisher=William Andrew Publishing |isbn=978-0-8155-1526-5 |access-date=2024-07-12 |archive-date=2024-10-04 |archive-url=https://web.archive.org/web/20241004183904/https://books.google.com/books?id=_J2ti4EkYpkC&pg=PAPA3171#v=onepage&q&f=false |url-status=live |url-access=subscription }}

Testosterone enanthate is the generic name of the drug and its {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|BAN|British Approved Name}}.{{cite book |vauthors=Morton IK, Hall JM |chapter=Testosterone |chapter-url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270 |page=270 |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |date=6 December 2012 |publisher=Springer Science & Business Media |isbn=978-94-011-4439-1 |access-date=11 May 2019 |archive-date=4 October 2024 |archive-url=https://web.archive.org/web/20241004183800/https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270#v=onepage&q&f=false |url-status=live }}{{cite web |title=Testosterone |website=Drugs.com |date=October 1, 2018 |url=https://www.drugs.com/international/testosterone.html |access-date=December 5, 2018 |archive-date=November 13, 2016 |archive-url=https://web.archive.org/web/20161113175707/https://www.drugs.com/international/testosterone.html |url-status=live }} It has also referred to as testosterone heptanoate.

Testosterone enanthate is marketed primarily under the brand name Delatestryl.

It is or has been marketed under a variety of other brand names as well, including, among others:{{Cite web|title=Testosterone cypionate profile and most popular brands in USA|url=http://downsizefitness.com/rankings/testosterone-cypionate/|access-date=2020-09-06|website=Anabolic Steroids Ratings and Reviews - downsizefitness.com|language=en|archive-date=2020-09-26|archive-url=https://web.archive.org/web/20200926103859/https://downsizefitness.com/rankings/testosterone-cypionate/|url-status=live}}

• Andro LA
• Andropository
• Cypionat
• Cypoprime
• Depandro
• Durathate
• Everone
• Testocyp
• Testostroval
• Testrin
• Testro LA
• Xyosted
• pharmaqo labs

{{See also|List of androgens/anabolic steroids available in the United States}}

Testosterone enanthate is available in the United States and widely elsewhere throughout the world.{{cite web | title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | access-date = 17 December 2016 | url = https://www.accessdata.fda.gov/scripts/cder/daf/ | archive-date = 16 November 2016 | archive-url = https://web.archive.org/web/20161116164727/http://www.accessdata.fda.gov/scripts/cder/daf/ | url-status = live }} Testosterone enanthate (testosterone heptanoate) is often available in concentrations of 200 mg per milliliter of fluid.{{Cite web | url=https://www.drugbank.ca/drugs/DB13944 | title=Testosterone enanthate | work=Drugbank | access-date=2019-05-09 | archive-date=2019-06-29 | archive-url=https://web.archive.org/web/20190629184318/https://www.drugbank.ca/drugs/DB13944 | url-status=live }}

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.{{cite book| vauthors = Karch SB |title=Drug Abuse Handbook, Second Edition|url=https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30|date=21 December 2006|publisher=CRC Press|isbn=978-1-4200-0346-8|pages=30–}}{{cite book| vauthors = Lilley LL, Snyder JS, Collins SR |title=Pharmacology for Canadian Health Care Practice |url= https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA50 |date=5 August 2016|publisher=Elsevier Health Sciences|isbn=978-1-77172-066-3|pages=50–}}

As of October 2017, an auto-injection formulation of testosterone enanthate was in preregistration for the treatment of hypogonadism in the United States.{{cite web | title=Testosterone enanthate auto-injection - Antares Pharma | website=AdisInsight | date=February 5, 2018 | url=https://adisinsight.springer.com/drugs/800037740 | access-date=December 5, 2018 | archive-date=September 9, 2017 | archive-url=https://web.archive.org/web/20170909005912/http://adisinsight.springer.com/drugs/800037740 | url-status=live }}

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.{{cite web | title = Antares Receives Fda Approval of Xyostedtm (Testosterone Enanthate) Injection for Testosterone Replacement Therapy in Adult Males | url = https://www.antarespharma.com/application/files/2715/3835/7488/XYOSTED_FDA_Approval_Final.pdf | access-date = 2019-05-05 | archive-date = 2019-05-04 | archive-url = https://web.archive.org/web/20190504214945/https://www.antarespharma.com/application/files/2715/3835/7488/XYOSTED_FDA_Approval_Final.pdf | url-status = live }}

{{Reflist}}

{{Testosterone}}

{{Androgens and antiandrogens}}

{{Androgen receptor modulators}}

{{Estrogen receptor modulators}}

Category:Anabolic–androgenic steroids

Category:Androstanes

Category:Enanthate esters

Category:Ketones

Category:Testosterone esters