| 词条 | Testosterone enanthate |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(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 | image = Testosterone enanthate.svg | width = 250px | image2 = Testosterone enanthate molecule ball.png | width2 = 250px | tradename = Delatestryl, others | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = Schedule IV | legal_UK = | legal_US = Schedule III | legal_status = | routes_of_administration = Intramuscular injection | class = Androgen; Anabolic steroid; Androgen ester | bioavailability = Oral: very low Intramuscular: high | protein_bound = | metabolism = Liver | elimination_half-life = Intramuscular: 4–5 days[1] | excretion = Urine | 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 | C=26 | H=40 | O=3 | molecular_weight = 400.603 g/mol | 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, sold under the brand name Delatestryl among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men.[1][2][3] It is also used in hormone therapy for transgender men.[4] It is given by injection into muscle usually once every two to four weeks.[3][5][6]Side effects of testosterone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[3] 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][3] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[3] Testosterone enanthate is a testosterone ester and a long-lasting prodrug of testosterone in the body.[5][1][2] 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.[17][2] Along with testosterone cypionate, testosterone undecanoate, and testosterone propionate, it is one of the most widely used testosterone esters.[7][2][3] In addition to its medical use, testosterone enanthate is used to improve physique and performance.[3] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[3] Medical uses{{See also|Androgen replacement therapy#Medical uses|Anabolic steroid#Medical}}Testosterone enanthate is used primarily in androgen replacement therapy.[2] It is the most widely used form of testosterone in androgen replacement therapy.[2] 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.[9] It is also used in masculinizing hormone therapy for transgender men.[4] {{Androgen replacement therapy formulations and dosages used in women}}Side effects{{See also|Anabolic steroid#Adverse effects|Androgen replacement therapy#Adverse effects}}Side effects of testosterone enanthate include virilization among others.[3]PharmacologyPharmacodynamics{{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). PharmacokineticsTestosterone 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.[6] 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.[6] {{Pharmacokinetics of testosterone esters}}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.[10][11] It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone.[10][11] {{Structural properties of major testosterone esters}}HistoryTestosterone enanthate was described as early as 1952[12] and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl.[13][2] Society and cultureGeneric namesTestosterone enanthate is the generic name of the drug and its {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|BAN|British Approved Name}}.[10][11][14][15] It has also referred to as testosterone heptanoate.[10][11][14][15]Brand namesTestosterone enanthate is marketed primarily under the brand name Delatestryl.[10][11][14][15] It is or has been marketed under a variety of other brand names as well including Andro LA, Andropository, Depandro, Durathate, Everone, Testrin, Testostroval, and Testro LA among others.[10][11][14][15] 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.[16][11][15] Legal statusTestosterone 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.[17][18] ResearchAs of October 2017, an auto-injection formulation of testosterone enanthate is in preregistration for the treatment of hypogonadism in the United States.[19] References1. ^1 {{cite book|author1=Eberhard Nieschlag|author2=Hermann M. Behre|author3=Susan Nieschlag|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–}} 2. ^1 2 3 4 5 6 {{cite book|author1=Eberhard Nieschlag|author2=Hermann M. Behre|author3=Susan Nieschlag|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–}} 3. ^1 2 3 4 5 6 7 8 {{cite book|author=William Llewellyn|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}} 4. ^1 {{cite journal | vauthors = Irwig MS | title = Testosterone therapy for transgender men | journal = Lancet Diabetes Endocrinol | volume = 5 | issue = 4 | pages = 301–311 | year = 2017 | pmid = 27084565 | doi = 10.1016/S2213-8587(16)00036-X | url = }} 5. ^1 {{cite book|author=Kenneth L. Becker|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}} 6. ^1 2 3 {{cite book|author1=Anita H. Payne|author2=Matthew P. Hardy|title=The Leydig Cell in Health and Disease|url=https://books.google.com/books?id=x4ttqKIAOg0C&pg=PA423|date=28 October 2007|publisher=Springer Science & Business Media|isbn=978-1-59745-453-7|pages=423–}} 7. ^1 {{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = Br. J. Pharmacol. | volume = 154 | issue = 3 | pages = 502–21 | year = 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 | url = }} 8. ^{{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 = J. Clin. Endocrinol. Metab. | volume = 101 | issue = 4 | pages = 1318–43 | year = 2016 | pmid = 27032319 | doi = 10.1210/jc.2016-1271 | url = }} 9. ^https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009165s031lbl.pdf 10. ^1 2 3 4 5 {{cite book|author=J. Elks|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}} 11. ^1 2 3 4 5 6 {{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}} 12. ^{{cite journal|last1=Junkmann|first1=Karl|title=Über protrahiert wirksame Androgene|year=1952|pages=85–92|doi=10.1007/978-3-642-49902-9_11}} 13. ^1 {{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA3171|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=3171–}} 14. ^1 2 3 {{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1}} 15. ^1 2 3 4 {{cite web | title=Testosterone | website=Drugs.com | date=October 1, 2018 | url=https://www.drugs.com/international/testosterone.html | access-date=December 5, 2018}} 16. ^{{cite web | title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | accessdate = 17 December 2016 | url = http://www.accessdata.fda.gov/scripts/cder/daf/}} 17. ^{{cite book|author=Steven B. Karch, MD, FFFLM|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–}} 18. ^{{cite book|author1=Linda Lane Lilley|author2=Julie S. Snyder|author3=Shelly Rainforth Collins|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–}} 19. ^{{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}} External links{{Androgens and antiandrogens}}{{Androgen receptor modulators}}{{Estrogen receptor modulators}} 5 : Alcohols|Androgens and anabolic steroids|Androstanes|Ketones|Testosterone esters |
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