| 词条 | Testosterone propionate |
| 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] propanoate | image = Testosterone propionate.svg | width = 250px | image2 = Testosterone propionate molecule ball.png | width2 = 250px | tradename = Testoviron, 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: very high | protein_bound = | metabolism = Liver | elimination_half-life = Intramuscular: 0.8 days[1][2] | excretion = Urine | CAS_number_Ref = | CAS_number = 57-85-2 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | PubChem = 5995 | DrugBank_Ref = | DrugBank = DB01420 | ChemSpiderID_Ref = | ChemSpiderID = 5774 | UNII = WI93Z9138A | ChEBI = 9466 | ChEMBL = 1170 | KEGG = D00959 | synonyms = TP; Testosterone propanoate; Testosterone 17β-propanoate; Propionyltestosterone; NSC-9166 | C=22 | H=32 | O=3 | molecular_weight = 344.495 g/mol | SMILES = CCC(=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/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = PDMMFKSKQVNJMI-BLQWBTBKSA-N }}Testosterone propionate, sold under the brand name Testoviron 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 has also been used to treat breast cancer in women.[4] It is given by injection into muscle usually once every two to three days.[3][5][6]Side effects of testosterone propionate 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 propionate is a testosterone ester and a relatively short-acting 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 propionate was discovered in 1936 and was introduced for medical use in 1937.[18][1] It was the first testosterone ester to be marketed, and was the major form of testosterone used in medicine until about 1960.[1][3] The introduction of longer-acting testosterone esters like testosterone enanthate, testosterone cypionate, and testosterone undecanoate starting in the 1950s resulted in testosterone propionate mostly being superseded.[1][3] As such, it is rarely used today.[3][25] In addition to its medical use, testosterone propionate 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 propionate is used primarily in androgen replacement therapy. It is specifically approved for the treatment of hypogonadism in men, breast cancer, low sexual desire, delayed puberty in boys, and menopausal symptoms.[9] Side effects{{See also|Anabolic steroid#Adverse effects|Androgen replacement therapy#Adverse effects}}Side effects of testosterone propionate include virilization among others.[3]PharmacologyPharmacodynamics{{See also|Testosterone#Mechanism of action|Anabolic steroid#Pharmacology}}{{Relative androgenic to anabolic activity in animals}}Testosterone propionate 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 propionate is administered in oil via intramuscular injection.[2][10] It has a relatively short elimination half-life and mean residence time of 0.8 days and 1.5 days, respectively.[2][10] As such, it has a short duration of action and must be administered two to three times per week.[11] {{Pharmacokinetics of testosterone esters}}Chemistry{{See also|Androgen ester|List of androgen esters}}Testosterone propionate, or testosterone 17β-propanoate, is a synthetic androstane steroid and a derivative of testosterone.[12][13] It is an androgen ester; specifically, it is the C17β propionate (propanoate) ester of testosterone.[12][13] {{Structural properties of major testosterone esters}}HistoryTestosterone esters were synthesized for the first time in 1936, and were found to have greatly improved potency relative to testosterone.[14] Among the esters synthesized, testosterone propionate was the most potent, and for this reason, was selected for further development, subsequently being marketed.[14] Testosterone propionate was introduced in 1937 by Schering AG in Germany under the brand name Testoviron.[3] It was the first ester of testosterone to be introduced,[1] and was the major form of testosterone used medically before 1960.[3] In the 1950s, longer-acting testosterone esters like testosterone enanthate and testosterone cypionate were introduced and superseded testosterone propionate.[1] Although rarely used nowadays due to its short duration,[15] testosterone propionate remains medically available.[3] Society and cultureGeneric namesTestosterone propionate is the generic name of the drug and its {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|BAN|British Approved Name}}.[12][13][16][17] It has also been referred to as testosterone propanoate or as propionyltestosterone.[12][13][16][17]Brand namesTestosterone propionate is or has been marketed under a variety of brand names including Agrovirin, Andronate, Andrusol-P, Masenate, Neo-Hombreol, Oreton, Perandren, Synandrol, Testoviron, and numerous others.[12][13][16][17] AvailabilityTestosterone propionate appears to no longer be available in the United States.[18] Legal statusTestosterone propionate, 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.[19][20] References1. ^1 2 3 4 5 6 {{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=9,315–}} 2. ^1 2 3 4 {{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=PA441|date=13 January 2010|publisher=Springer Science & Business Media|isbn=978-3-540-78355-8|pages=441–446}} 3. ^1 2 3 4 5 6 7 8 9 10 11 12 13 {{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT357|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=357–361,413,426,607}} 4. ^{{cite journal | vauthors = Bolour S, Braunstein G | title = Testosterone therapy in women: a review | journal = Int. J. Impot. Res. | volume = 17 | issue = 5 | pages = 399–408 | year = 2005 | pmid = 15889125 | doi = 10.1038/sj.ijir.3901334 | 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. ^{{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. ^{{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. ^http://adisinsight.springer.com/drugs/800013172 10. ^1 2 {{cite journal | vauthors = Behre HM, Abshagen K, Oettel M, Hübler D, Nieschlag E | title = Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies | journal = Eur. J. Endocrinol. | volume = 140 | issue = 5 | pages = 414–9 | year = 1999 | pmid = 10229906 | doi = 10.1530/eje.0.1400414| url = | citeseerx = 10.1.1.503.1752 }} 11. ^{{cite book | first1 = Sai-Ching Jim | last1 = Yeung | first2 = Carmen P. | last2= Escalante | first3 = Robert F. | last3 = Gagel | name-list-format = vanc | title = Medical Care of Cancer Patients|url=https://books.google.com/books?id=XxfjqF1A0TkC&pg=PA247|year=2009|publisher=PMPH-USA|isbn=978-1-60795-008-0|pages=247–}} 12. ^1 2 3 4 {{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}} 13. ^1 2 3 4 {{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}} 14. ^1 2 {{cite journal | vauthors = Korenchevsky V, Dennison M, Eldridge M | title = The prolonged treatment of castrated and ovariectomized rats with testosterone propionate | journal = Biochem. J. | volume = 31 | issue = 3 | pages = 475–85 | year = 1937 | pmid = 16746360 | pmc = 1266958 | doi = 10.1042/bj0310475| url = }} 15. ^1 {{cite book|author1=Christopher R. Chapple|author2=William D. Steers|title=Practical Urology: Essential Principles and Practice: Essential Principles and Practice|url=https://books.google.com/books?id=A9m8TkdCUqEC&pg=PA228|date=10 May 2011|publisher=Springer Science & Business Media|isbn=978-1-84882-034-0|pages=228–}} 16. ^1 2 {{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}} 17. ^1 2 {{Cite web | url=https://www.drugs.com/international/testosterone.html | title=Testosterone}} 18. ^{{cite web | title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | accessdate = 16 November 2016 | url = http://www.accessdata.fda.gov/scripts/cder/daf/}} 19. ^{{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–}} 20. ^{{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–}} External links{{Androgens and antiandrogens}}{{Androgen receptor modulators}}{{Estrogen receptor modulators}} 5 : Androgens and anabolic steroids|Androstanes|Ketones|Propionate esters|Testosterone esters |
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