Testosterone enanthate

{{short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[''a'']phenanthren-17-yl] heptanoate | image = Testosterone enanthate.svg | image_class = skin-invert-image | width = 250px | image2 = Testosterone enanthate molecule ball.png | image_class2 = bg-transparent | width2 = 250px

| C=26 | H=40 | O=3 | SMILES = CCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = VOCBWIIFXDYGNZ-IXKNJLPQSA-N }}

'''Testosterone enanthate''' is used in the treatment of low testosterone levels in men.<ref name="NieschlagBehre2012">{{cite book|vauthors=Nieschlag E, Behre HM, Nieschlag S|title=Testosterone: Action, Deficiency, Substitution|url=https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA315|date=26 July 2012|publisher=Cambridge University Press|isbn=978-1-107-01290-5|pages=315–|access-date=3 January 2018|archive-date=7 April 2024|archive-url=https://web.archive.org/web/20240407172405/https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA315#v=onepage&q&f=false|url-status=live}}</ref><ref name="NieschlagBehre2010">{{cite book|vauthors=Nieschlag E, Behre HM, Nieschlag S|title=Andrology: Male Reproductive Health and Dysfunction|url=https://books.google.com/books?id=mEgckDNkonUC&pg=PA442|date=13 January 2010|publisher=Springer Science & Business Media|isbn=978-3-540-78355-8|pages=442–|access-date=19 November 2016|archive-date=14 January 2023|archive-url=https://web.archive.org/web/20230114074708/https://books.google.com/books?id=mEgckDNkonUC&pg=PA442|url-status=live}}</ref><ref name="Llewellyn2011">{{cite book|vauthors=Llewellyn W|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT208|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=208–211|access-date=2018-01-03|archive-date=2024-04-07|archive-url=https://web.archive.org/web/20240407172405/https://books.google.com/books?id=afKLA-6wW0oC&pg=PT208#v=onepage&q&f=false|url-status=live}}</ref> It is also used in hormone therapy for women<ref name="pmid27084565">{{cite journal | vauthors = Irwig MS | title = Testosterone therapy for women | journal = The Lancet. Diabetes & Endocrinology | volume = 5 | issue = 4 | pages = 301–311 | date = April 2017 | pmid = 27084565 | doi = 10.1016/S2213-8587(16)00036-X }}</ref> and transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.<ref name="Llewellyn2011" /><ref name="Becker2001">{{cite book|vauthors=Becker KL|title=Principles and Practice of Endocrinology and Metabolism|url=https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=1185, 1187|access-date=2018-01-03|archive-date=2024-04-07|archive-url=https://web.archive.org/web/20240407172405/https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185#v=onepage&q&f=false|url-status=live}}</ref><ref name="PayneHardy2007">{{cite book |doi=10.1007/978-1-59745-453-7_29 |chapter=The Leydig Cell as a Target for Male Contraception |title=The Leydig Cell in Health and Disease |pages=415–442 |series=Contemporary Endocrinology |year=2007 | vauthors = Luetjens CM, Wistuba J, Weinbauer G, Nieschlag E |publisher=Humana Press |isbn=978-1-58829-754-9 }}</ref>

Side effects of testosterone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.<ref name="Llewellyn2011" /> 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).<ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref><ref name="Llewellyn2011" /> Testosterone enanthate is a testosterone ester and a long-lasting prodrug of testosterone in the body.<ref name="Becker2001" /><ref name="NieschlagBehre2012" /><ref name="NieschlagBehre2010" /> Because of this, it is considered to be a natural and bioidentical form of testosterone,<ref name="pmid27032319">{{cite journal | vauthors = Santoro N, Braunstein GD, Butts CL, Martin KA, McDermott M, Pinkerton JV | title = Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 101 | issue = 4 | pages = 1318–1343 | date = April 2016 | pmid = 27032319 | doi = 10.1210/jc.2016-1271 | doi-access = free }}</ref> which makes it useful for producing masculinization and suitable for androgen replacement therapy.<ref name="Llewellyn2011" /> Esterase enzymes break the ester bond in testosterone enanthate, releasing free testosterone and enanthic acid through hydrolysis.<ref>{{cite journal | doi=10.1210/clinem/dgab772 | title=Testosterone Therapy with Subcutaneous Injections: A Safe, Practical, and Reasonable Option | date=2022 | journal=The Journal of Clinical Endocrinology & Metabolism | volume=107 | issue=3 | pages=614–626 | pmid=34698352 | pmc=9006970 | vauthors = Figueiredo MG, Gagliano-Jucá T, Basaria S }}</ref> <ref>{{cite web | url=https://taylorandfrancis.com/knowledge/Medicine_and_healthcare/Pharmaceutical_medicine/Testosterone_enantate | title=Testosterone enantate - Knowledge and References }}</ref> <ref>{{cite journal | url=https://academic.oup.com/humupd/article/10/5/409/769303 | doi=10.1093/humupd/dmh035 | title=Testosterone replacement therapy: Current trends and future directions | date=2004 | journal=Human Reproduction Update | volume=10 | issue=5 | pages=409–419 | pmid=15297434 | vauthors = Nieschlag E, Behre H, Bouchard P, Corrales J, Jones T, Stalla G, Webb S, Wu F }}</ref> This process ensures a sustained release of testosterone in the body.<ref>{{cite journal | url=https://link.springer.com/article/10.1007/s12010-020-03483-8 | doi=10.1007/s12010-020-03483-8 | title=Marine Bacterial Esterases: Emerging Biocatalysts for Industrial Applications | date=2021 | journal=Applied Biochemistry and Biotechnology | volume=193 | issue=4 | pages=1187–1214 | pmid=33411134 | vauthors=Barzkar N, Sohail M, Tamadoni Jahromi S, Gozari M, Poormozaffar S, Nahavandi R, Hafezieh M | access-date=2024-11-06 | archive-date=2023-09-07 | archive-url=https://web.archive.org/web/20230907080211/https://link.springer.com/article/10.1007/s12010-020-03483-8 | url-status=live | url-access=subscription }}</ref>

Testosterone enanthate was introduced for medical use in 1954.<ref name="Publishing2013" /><ref name="NieschlagBehre2010" /> Along with testosterone cypionate, testosterone undecanoate, and testosterone propionate, it is one of the most widely used testosterone esters.<ref name="pmid18500378" /><ref name="NieschlagBehre2010" /><ref name="Llewellyn2011" /> In addition to its medical use, testosterone enanthate is used to improve physique and performance.<ref name="Llewellyn2011" /> The drug is a controlled substance in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" />

==Medical uses== {{See also|Androgen replacement therapy#Medical uses|Anabolic steroid#Medical}} Testosterone enanthate is used primarily in androgen replacement therapy.<ref name="NieschlagBehre2010" /><ref>{{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 }}</ref> It is the most widely used form of testosterone in androgen replacement therapy.<ref name="NieschlagBehre2010" /> 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.<ref name="Delatestryl-Label">{{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 }}</ref> It is also used in masculinizing hormone therapy for transgender men.<ref name="pmid27084565" />

==Side effects== {{See also|Anabolic steroid#Adverse effects|Androgen replacement therapy#Adverse effects}} Side effects of testosterone enanthate include virilization among others.<ref name="Llewellyn2011" /> Approximately 10 percent of testosterone enanthate will be converted to 5α-dihydrotestosterone in men without endocrine disease or taking medication that disrupts this conversion, such as finasteride.<ref>{{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}}</ref> 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.<ref>{{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 }}</ref><ref>{{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 }}</ref> Testosterone enanthate can also be converted to estradiol (E2) by the aromatase enzyme,<ref name="semanticscholar.org">{{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 }}</ref> 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.<ref name="semanticscholar.org"/>

==Pharmacology== ===Pharmacodynamics=== {{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;<ref name="Llewellyn2011" /> still, the relative potency of these effects can depend on various factors and is a topic of ongoing research.<ref name="Ceponis-2017">{{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 }}</ref><ref name="pmid12017555">{{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 }}</ref> 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).<ref name="Ceponis-2017"/> 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)<ref>{{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 }}</ref> at lower levels.<ref name="Ceponis-2017"/>

===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.<ref name="PayneHardy2007" /> 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.<ref name="PayneHardy2007"/> 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.<ref>{{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 }}</ref><ref>{{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 }}</ref> 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.<ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 | article-number=227 | pmid=31222590 | vauthors = Yang D, Li W, Fang L, Liu C | url-access=subscription }}</ref><ref>{{cite journal | title=Influence of HLB values of surfactants on ephedrine release from emulsified liquid systems | journal=Journal of Pharmaceutical Sciences | date=1971 | volume=60 | issue=12 | pages=1830–1835 | doi=10.1002/jps.2600601212 | pmid=5157998 | bibcode=1971JPhmS..60.1830W | url=https://www.jpharmsci.org/article/S0022-3549(15)38234-4/abstract | vauthors = Waggoner WG, Fincher JH }}</ref>

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

Testosterone enanthate, or testosterone 17β-heptanoate, is a synthetic androstane steroid and a derivative of testosterone.<ref name="Elks2014">{{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}}</ref><ref name="IndexNominum2000">{{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}}</ref> It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone.<ref name="Elks2014" /><ref name="IndexNominum2000" />

==History== Testosterone enanthate was described as early as 1952<ref name="Junkmann1952">{{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 }}</ref> and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl.<ref name="Publishing2013">{{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 }}</ref><ref name="NieschlagBehre2010" />

==Society and culture== ===Generic names=== ''Testosterone enanthate'' is the generic name of the drug and its {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|BAN|British Approved Name}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012">{{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 }}</ref><ref name="Drugs.com">{{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 }}</ref> It has also referred to as ''testosterone heptanoate''.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

=== Brand names === Testosterone enanthate is marketed primarily under the brand name Delatestryl.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

It is or has been marketed under a variety of other brand names as well, including, among others:<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /><ref>{{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}}</ref> * Andro LA * Andropository * Depandro * Durathate * Everone * Testostroval * Testrin * Testro LA * Xyosted * pharmaqo labs

===Availability=== {{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.<ref name="Drugs@FDA">{{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 }}</ref><ref name="IndexNominum2000" /><ref name="Drugs.com" /> Testosterone enanthate (testosterone heptanoate) is often available in concentrations of 200 mg per milliliter of fluid.<ref>{{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 }}</ref>

===Legal status=== 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.<ref name="FFFLM2006">{{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–}}</ref><ref name="LilleySnyder2016">{{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–}}</ref>

==Research== As of October 2017, an auto-injection formulation of testosterone enanthate was in preregistration for the treatment of hypogonadism in the United States.<ref name="AdisInsight">{{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 }}</ref>

===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.<ref>{{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 }}</ref>

== References == {{Reflist}}

Category:Androgens Category:Androstanes Category:Enanthate esters Category:Ketones Category:Testosterone esters