View source for 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
| width2 = 250px

<!--Clinical data-->
| tradename = Delatestryl, Xyosted, others
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = Schedule IV
| legal_UK =
| legal_US = Schedule III
| legal_status =
| routes_of_administration = [[Intramuscular injection]], [[subcutaneous injection]]
| class = [[Androgen]]; [[Anabolic steroid]]; [[Androgen ester]]

<!--Pharmacokinetic data-->
| bioavailability = [[Oral administration|Oral]]: very low<br />[[Intramuscular injection|Intramuscular]]: high
| protein_bound =
| metabolism = [[Liver]]
| elimination_half-life = [[Intramuscular injection|Intramuscular]]: 4–5 days<ref name="PayneHardy2007" />
| excretion = [[Urine]]

<!--Identifiers-->
| CAS_number_Ref =
| CAS_number = 315-37-7
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| PubChem = 9416
| DrugBank_Ref =
| DrugBank = DB13944
| ChemSpiderID_Ref =
| ChemSpiderID = 9045
| UNII = 7Z6522T8N9
| ChEBI = 9464
| ChEMBL = 1200335
| KEGG = D00958
| synonyms = TE; Testosterone heptanoate; Testosterone 17β-heptanoate; NSC-17591

<!--Chemical data-->
| 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
}}

<!-- Definition and medical uses -->
'''Testosterone enanthate''' is used in the treatment of [[male hypogonadism|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 [[masculinizing hormone therapy|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]]{{medical citation needed|date=October 2024}}. It is given by [[intramuscular injection|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 and mechanism of action -->
[[Side effect]]s of testosterone enanthate include [[symptom]]s of [[virilization|masculinization]] like [[acne]], [[hirsutism|increased hair growth]], [[voice deepening|voice changes]], and increased [[libido|sexual desire]].<ref name="Llewellyn2011" /> The drug is a [[synthetic compound|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 (medication)|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 make it useful for producing masculinization and suitable for [[androgen replacement therapy]].<ref name="Llewellyn2011" /> Esterase enzymes break the ester bond in testosterone enantate, 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>

<!-- History, society, and culture -->
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 [[ester]]s.<ref name="pmid18500378" /><ref name="NieschlagBehre2010" /><ref name="Llewellyn2011" /> In addition to its medical use, testosterone enanthate is used to [[performance-enhancing substance|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 effect]]s of testosterone enanthate include [[virilization]] among others.<ref name="Llewellyn2011" /> Approximately 10 percent of testosterone enanthate will be converted to [[Dihydrotestosterone|5α-dihydrotestosterone]] in normal men.<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 [[Insulin-like growth factor-binding protein|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 inhibitor]]s, such as [[anastrozole]], [[letrozole]], [[exemestane]], etc., can help to prevent the subsequent estrogenic activity of testosterone enanthate [[metabolite]]s 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 [[androgen]]ic 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|5α-reductase]] enzymes into [[5α-Dihydroethisterone|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 [[Aromatization|aromatized]] (not converted into an estrogen), both testosterone and DHT are [[Bioactive compound|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 follicle]]s)<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&nbsp;days and a [[mean residence time]] of 8.5&nbsp;days when used as a [[depot injection|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 | page=227 | pmid=31222590 | vauthors = Yang D, Li W, Fang L, Liu C | url-access=subscription }}</ref><ref>https://www.jpharmsci.org/article/S0022-3549(15)38234-4/abstract</ref>

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

Testosterone enanthate, or testosterone 17β-heptanoate, is a [[synthetic compound|synthetic]] [[androstane]] [[steroid]] and a [[chemical derivative|derivative]] of [[testosterone (medication)|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 term|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
* Cypionat
* Cypoprime
* Depandro
* Durathate
* Everone
* Testocyp
* 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&nbsp;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 [[Controlled Substances Act#Schedule III controlled substances|schedule III]] [[controlled substance]] in the [[United States]] under the [[Controlled Substances Act]] and a [[Controlled Drugs and Substances Act#Schedule IV|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 [[autoinjector|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 [[Autoinjector|auto-injector]] that dispenses testosterone enanthate. Xyosted is the first FDA-approved [[Subcutaneous injection|subcutaneous]] testosterone enanthate product for [[Androgen replacement therapy|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}}

{{Testosterone}}
{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}
{{Estrogen receptor modulators}}

[[Category:Anabolic–androgenic steroids]]
[[Category:Androstanes]]
[[Category:Enanthate esters]]
[[Category:Ketones]]
[[Category:Testosterone esters]]