Testosterone enanthate

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Testosterone enanthate
Testosterone enanthate.svg
Testosterone enanthate molecule ball.png
Clinical data
Trade namesDelatestryl, Xyosted, others
SynonymsTE; Testosterone heptanoate; Testosterone 17β-heptanoate; NSC-17591
Routes of
administration
Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: very low
Intramuscular: high
MetabolismLiver
Elimination half-lifeIntramuscular: 4–5 days[1]
ExcretionUrine
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard100.005.686 Edit this at Wikidata
Chemical and physical data
FormulaC26H40O3
Molar mass400.603 g/mol g·mol−1
3D model (JSmol)

Testosterone enanthate, sold under the brand names Delatestryl and Xyosted among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men.[2][3][4] It is also used in hormone therapy for transgender men.[5] It is given by injection into muscle usually once every one to four weeks.[4][6][1]

Side effects of testosterone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[4] 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).[7][4] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[4] Testosterone enanthate is a testosterone ester and a long-lasting prodrug of testosterone in the body.[6][2][3] Because of this, it is considered to be a natural and bioidentical form of testosterone.[8]

Testosterone enanthate was introduced for medical use in 1954.[9][3] Along with testosterone cypionate, testosterone undecanoate, and testosterone propionate, it is one of the most widely used testosterone esters.[7][3][4] In addition to its medical use, testosterone enanthate is used to improve physique and performance.[4] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[4]

Medical uses[edit]

Testosterone enanthate is used primarily in androgen replacement therapy.[3] It is the most widely used form of testosterone in androgen replacement therapy.[3] 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.[10] It is also used in masculinizing hormone therapy for transgender men.[5]

Androgen replacement therapy formulations and dosages used in women

Route Medication Form(s) Major brand name(s) Dosage
Oral Testosterone undecanoatea Capsule Andriol, Jatenzo 40–80 mg 1x/1–2 days
Methyltestosteroneb Tablet Metandren; Estratest 0.5–10 mg/day
Normethandronea,b Tablet Ginecoside 5 mg/day
Tibolonea Tablet Livial 1.25–2.5 mg/day
Prasterone (DHEA)c Tablet N/A 25–100 mg/day
Sublingual Testosteroned Tablet N/A 0.25–0.5 mg/day
Methyltestosterone Tablet Metandren 0.25 mg/day
Transdermal Testosteronea Patch Intrinsa 150–300 μg/day
Testosterone Cream; Gel AndroGel 5–10 mg/day
Vaginal Testosteroned Cream; Gel N/A ? mg 1x/1–3 days
Testosteroned Suppository N/A 1 mg 1x/2 days
Prasterone (DHEA) Insert Intrarosa 6.5 mg/day
Intramuscular Testosterone enanthateb Oil Delatestryl; Primodian Depot 25–100 mg 1x/4–6 weeks
Testosterone cypionateb Oil Depo-Testost.; Depo-Testadiol 25–100 mg 1x/4–6 weeks
Testosterone isobutyratea,b Water Femandren M, Folivirin 25–50 mg 1x/4–6 weeks
Testosterone EBHb,e Oil Climacteron 150 mg 1x/4–8 weeks
Nandrolone decanoate Oil Deca-Durabolin 25–50 mg 1x/6–12 weeks
Prasterone enanthatea,b Oil Gynodian Depot 200 mg 1x/4–6 weeks
Subcutaneous Testosterone Implant Testopel 50–100 mg 1x/3–6 months
Footnotes: a = Not available or no longer available in the United States. b = Alone and/or in combination with an estrogen. c = Over-the-counter. d = Compounded only. e = Discontinued. Sources: See template.

Androgen/anabolic steroid dosages for breast cancer

Route/form Androgen Dosage
Oral Methyltestosterone 30–200 mg/day
Fluoxymesterone 10–40 mg 3x/day
Calusterone 40 mg 4x/day
Normethandrone 40 mg/day
IM injection Testosterone propionate 50–100 mg 3x/week
Testosterone enanthate 200–400 mg 1x/2–4 weeks
Testosterone cypionate 200–400 mg 1x/2–4 weeks
Methandriol (aq. susp.) 100 mg 3x/week
Androstanolone (aq. susp.) 300 mg 3x/week
Drostanolone propionate 100 mg 3x/week
Nandrolone decanoate 50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate 50–100 mg/week
Notes: Dosages are not necessarily equivalent. Sources: See template.

Side effects[edit]

Side effects of testosterone enanthate include virilization among others.[4] Approximately 10 percent of testosterone enanthate will be converted to dihydrotestosterone in normal men.[11] 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 igf-bp.[12][13] Testosterone enanthate can also be converted to estradiol by aromatase,[14] which may lead to gynecomastia in males. Aromatase inhibitors can help to prevent the estrogenic activity of testosterone enanthate in the body.[15]

Pharmacology[edit]

Pharmacodynamics[edit]

Relative androgenic to anabolic
activity in animals

Medication Ratio
Testosterone 1:1
Testosterone cypionate 1:1
Testosterone enanthate 1:1
Methyltestosterone 1:1
Fluoxymesterone 1:2
Oxymetholone 1:3
Oxandrolone 1:3–1:13
Nandrolone decanoate 1:2.5–1:4
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).

Pharmacokinetics[edit]

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.[1] 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.[1]

Pharmacokinetics of testosterone esters

Testosterone ester Form Route of administration Elimination half-life Mean residence time
Testosterone undecanoate Oil-filled capsules Oral 1.6 hours 3.7 hours
Testosterone propionate Oil solution Intramuscular injection 0.8 days 1.5 days
Testosterone enanthate Castor oil solution Intramuscular injection 4.5 days 8.5 days
Testosterone undecanoate Tea seed oil solution Intramuscular injection 20.9 days 34.9 days
Testosterone undecanoate Castor oil solution Intramuscular injection 33.9 days 36.0 days
Testosterone buciclatea Aqueous suspension Intramuscular injection 29.5 days 60.0 days
Notes: Testosterone cypionate has very similar pharmacokinetics to TE. Footnotes: a = Never marketed. Sources: See template.

Parenteral durations of androgens/anabolic steroids

Compound Brand name(s) Type Duration
Testosterone (aq. susp.) Andronaq, Sterotate, Virosterone Androgen 2–3 days
Testosterone propionate Androteston, Perandren, Testoviron Androgen 3–4 days
Testosterone phenylpropionate Androteston P. P. Androgen 8 days
Testosterone isobutyrate (aq. susp.) Agovirin-Depot, Perandren M Androgen 14 days
Testosterone propionate/valerate/undecylenate Triolandren Androgen 10–20 days
Testosterone propionate/ketolaurate Testosid-Depot Androgen 14–20 days
Testosterone enanthate Delatestryl Androgen 14–20 days
Testosterone cypionate Depovirin Androgen 14–20 days
Testosterone propionate/phenylpropionate/isocaproate/decanoate Sustanon-250 Androgen 28 days
Testosterone undecanoate Aveed, Nebido Androgen 100 days
Testosterone buciclate (aq. susp.)a Androgen 90–120 days
Nandrolone phenylpropionate Durabolin Anabolic 10 days
Nandrolone decanoate Deca-Durabolin Anabolic 21 days
Methandriol (aq. susp.) Notandron, Protandren Androgen 8 days
Methandriol bisenanthoyl acetate Notandron-Depot Androgen 16 days
Metenolone acetate Primobolan Anabolic 3 days
Metenolone enanthate Primobolan-Depot Anabolic 14 days
Note: All are via i.m. injection of oil solution unless noted otherwise. Footnotes: a = Studied, but never marketed. Sources: See template.

Chemistry[edit]

Testosterone enanthate, or testosterone 17β-heptanoate, is a synthetic androstane steroid and a derivative of testosterone.[16][17] It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone.[16][17]

Structural properties of major testosterone esters

Androgen Structure Ester Rel. MWb Rel. Tc Durationd
Position Moiety Type Lengtha Rank Group
Testosterone
Testosteron.svg
1.00 1.00 6 Short
Testosterone propionate
Testosterone propionate.svg
C17β Propanoic acid Straight-chain fatty acid 3 1.19 0.84 6 Short
Testosterone isobutyrate
Testosterone isobutyrate.svg
C17β Isobutyric acid Aromatic fatty acid – (~3) 1.24 0.80 5 Moderate
Testosterone cypionate
Testosterone cypionate.svg
C17β Cyclopentylpropanoic acid Aromatic fatty acid – (~6) 1.43 0.70 4 Moderate
Testosterone enanthate
Testosterone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid 7 1.39 0.72 3 Moderate
Testosterone undecanoate
Testosterone undecanoate.svg
C17β Undecanoic acid Straight-chain fatty acid 11 1.58 0.63 2 Long
Testosterone buciclatee
Testosteronebuciclate structure.png
C17β Bucyclic acidf Aromatic carboxylic acid – (~9) 1.58 0.63 1 Long
Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative molecular weight. c = Relative testosterone content by weight (i.e., relative androgenic potency). d = Duration by intramuscular or subcutaneous injection. e = Never marketed. f = Bucyclic acid = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles.

History[edit]

Testosterone enanthate was described as early as 1952[18] and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl.[9][3]

Society and culture[edit]

Generic names[edit]

Testosterone enanthate is the generic name of the drug and its USAN and BAN.[16][17][19][20] It has also referred to as testosterone heptanoate.[16][17][19][20]

Brand names[edit]

Testosterone enanthate is marketed primarily under the brand name Delatestryl.[16][17][19][20]

It is or has been marketed under a variety of other brand names as well, including, among others:[16][17][19][20]

  • Andro LA
  • Andropository
  • Depandro
  • Durathate
  • Everone
  • Testostroval
  • Testrin
  • Testro LA
  • Xyosted

Availability[edit]

Testosterone enanthate is available in the United States and widely elsewhere throughout the world.[21][17][20] Testosterone enanthate (testosterone heptanoate) is often available in concentrations of 200mg per milliliter of fluid.[22]

Legal status[edit]

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.[23][24]

Research[edit]

As of October 2017, an auto-injection formulation of testosterone enanthate was in preregistration for the treatment of hypogonadism in the United States.[25]

Xyosted[edit]

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.[26]

References[edit]

  1. ^ a b c d Luetjens, Craig Marc; Wistuba, Joachim; Weinbauer, Gerhard; Nieschlag, Eberhard (2007). "The Leydig Cell as a Target for Male Contraception". The Leydig Cell in Health and Disease. Contemporary Endocrinology. pp. 415–442. doi:10.1007/978-1-59745-453-7_29. ISBN 978-1-58829-754-9.
  2. ^ a b Eberhard Nieschlag; Hermann M. Behre; Susan Nieschlag (26 July 2012). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 315–. ISBN 978-1-107-01290-5.
  3. ^ a b c d e f g Eberhard Nieschlag; Hermann M. Behre; Susan Nieschlag (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 442–. ISBN 978-3-540-78355-8.
  4. ^ a b c d e f g h i William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 208–211. ISBN 978-0-9828280-1-4.
  5. ^ a b Irwig, Michael S (April 2017). "Testosterone therapy for transgender men". The Lancet Diabetes & Endocrinology. 5 (4): 301–311. doi:10.1016/S2213-8587(16)00036-X. PMID 27084565.
  6. ^ a b Kenneth L. Becker (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185, 1187. ISBN 978-0-7817-1750-2.
  7. ^ a b Kicman, A T (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  8. ^ Santoro, Nanette; Braunstein, Glenn D.; Butts, Cherie L.; Martin, Kathryn A.; McDermott, Michael; Pinkerton, JoAnn V. (April 2016). "Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement". The Journal of Clinical Endocrinology & Metabolism. 101 (4): 1318–1343. doi:10.1210/jc.2016-1271. PMID 27032319.
  9. ^ a b "Testosterone Enanthate". p. 35t. in William Andrew Publishing (2007). "T". Pharmaceutical Manufacturing Encyclopedia. pp. 1t–242t. doi:10.1016/B978-0-8155-1526-5.50024-6. ISBN 978-0-8155-1526-5.
  10. ^ https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009165s031lbl.pdf[full citation needed]
  11. ^ "DHT (dihydrotestosterone): What is DHT's role in baldness?".
  12. ^ Ashton, WS; Degnan, BM; Daniel, A; Francis, GL (1995). "Testosterone increases insulin-like growth factor-1 and insulin-like growth factor-binding protein". Annals of Clinical and Laboratory Science. 25 (5): 381–8. PMID 7486812.
  13. ^ Hoeh, Michael P.; Levine, Laurence A. (March 2015). "Management of Recurrent Ischemic Priapism 2014: A Complex Condition with Devastating Consequences". Sexual Medicine Reviews. 3 (1): 24–35. doi:10.1002/smrj.37. PMID 27784569.
  14. ^ Ishikawa, Toshio; Glidewell-Kenney, Christine; Jameson, J. Larry (February 2006). "Aromatase-independent testosterone conversion into estrogenic steroids is inhibited by a 5α-reductase inhibitor". The Journal of Steroid Biochemistry and Molecular Biology. 98 (2–3): 133–138. doi:10.1016/j.jsbmb.2005.09.004. PMID 16386416.
  15. ^ Ishikawa, Toshio; Glidewell-Kenney, Christine; Jameson, J. Larry (February 2006). "Aromatase-independent testosterone conversion into estrogenic steroids is inhibited by a 5α-reductase inhibitor". The Journal of Steroid Biochemistry and Molecular Biology. 98 (2–3): 133–138. doi:10.1016/j.jsbmb.2005.09.004. PMID 16386416.
  16. ^ a b c d e f J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN 978-1-4757-2085-3.
  17. ^ a b c d e f g Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN 978-3-88763-075-1.
  18. ^ Junkmann, Karl (1952). "Über protrahiert wirksame Androgene" [Over protracted effective androgens]. Festschrift zum 75. Geburtstag. pp. 85–92. doi:10.1007/978-3-642-49902-9_11. ISBN 978-3-642-49610-3.
  19. ^ a b c d Morton, Ian K. M.; Hall, Judith M. (6 December 2012). "Testosterone". Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. p. 270. ISBN 978-94-011-4439-1.
  20. ^ a b c d e "Testosterone". Drugs.com. October 1, 2018. Retrieved December 5, 2018.
  21. ^ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 17 December 2016.
  22. ^ "Testosterone enanthate".
  23. ^ Steven B. Karch, MD, FFFLM (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.CS1 maint: Multiple names: authors list (link)
  24. ^ Linda Lane Lilley; Julie S. Snyder; Shelly Rainforth Collins (5 August 2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. pp. 50–. ISBN 978-1-77172-066-3.
  25. ^ "Testosterone enanthate auto-injection - Antares Pharma". AdisInsight. February 5, 2018. Retrieved December 5, 2018.
  26. ^ Antares Receives FDA Approval of Xyosted (Testosterone Enanthate) Injection for Testosterone Replacement Therapy in Adult Males