| 词条 | Trenbolone |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470612755 | IUPAC_name = (8S,13S,14S,17S)-17-Hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-one | image = Trenbolone.svg | width = 225px | tradename = | Drugs.com = {{Drugs.com|international|trenbolone}} | pregnancy_category = X | legal_CA = Schedule IV | legal_US = Schedule III | legal_status = | routes_of_administration = Intramuscular injection (as esters) | class = Androgen; Anabolic steroid; Progestogen | bioavailability = Intramuscular: 100%{{Citation needed|date=November 2017}} | protein_bound = | metabolism = Liver | elimination_half-life = 48–72 hours{{Citation needed|date=November 2017}} | excretion = Urine | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 10161-33-8 | ATC_prefix = None | PubChem = 25015 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 23383 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = P53R4420TR | synonyms = Trienolone; Trienbolone; RU-2341; Δ9,11-Nandrolone; 19-Nor-δ9,11-testosterone; Estra-4,9,11-trien-17β-ol-3-one | C=18 | H=22 | O=2 | molecular_weight = 270.37 g/mol | SMILES = O=C4\\C=C2/C(=C1/C=C\\[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h8-10,15-17,20H,2-7H2,1H3/t15-,16+,17+,18+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = MEHHPFQKXOUFFV-OWSLCNJRSA-N }}Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed.[1][2][3][4][5] Trenbolone ester prodrugs, including trenbolone acetate (brand names Finajet, Finaplix, others) and trenbolone hexahydrobenzylcarbonate (brand names Parabolan, Hexabolan), are or have been marketed for veterinary and clinical use.[1][2][3][5][6][7] Trenbolone acetate is used in veterinary medicine in livestock to increase muscle growth and appetite, while trenbolone hexahydrobenzylcarbonate was formerly used clinically in humans but is now no longer marketed.[1][2][3][5] In addition, although it is not approved for clinical or veterinary use, trenbolone enanthate is sometimes sold on the black market under the nickname Trenabol.[5] UsesVeterinaryTrenbolone, as trenbolone acetate, improves muscle mass, feed efficiency, and mineral absorption in cattle.[5] Side effects{{See also|Anabolic steroid#Adverse effects}}PharmacologyPharmacodynamicsTrenbolone has both anabolic and androgenic effects.[5] Once metabolized, trenbolone esters have the effect of increasing ammonium ion uptake by muscles, leading to an increase in the rate of protein synthesis. It may also have the secondary effects of stimulating appetite and decreasing the rate of catabolism, as all anabolic steroids are believed to; however, catabolism likely increases significantly once the steroid is no longer taken.[8] At least one study in rats has shown trenbolone to cause gene expression of the androgen receptor (AR) at least as potent as dihydrotestosterone (DHT). This evidence tends to indicate trenbolone can cause an increase in male secondary sex characteristics without the need to convert to a more potent androgen in the body.[9] Studies on metabolism are mixed, with some studies showing that it is metabolized by aromatase or 5α-reductase into estrogenic compounds, or into 5α-reduced androgenic compounds, respectively.[10][11] Trenbolone has potency five times as high as that of testosterone.[5][12][13] Trenbolone also binds with high affinity to the progesterone receptor,[5][13][14][15] Trenbolone binds to the glucocorticoid receptor, as well.[14] PharmacokineticsTo prolong its elimination half-life, trenbolone is administered as a prodrug as an ester conjugate such as trenbolone acetate, trenbolone enanthate, or trenbolone hexahydrobenzylcarbonate.[1][2][3][5] Plasma lipases then cleave the ester group in the bloodstream leaving free trenbolone.{{citation needed|date=June 2016}} Trenbolone and 17-epitrenbolone are both excreted in urine as conjugates that can be hydrolyzed with beta-glucuronidase.[16] This implies that trenbolone leaves the body as beta-glucuronides or sulfates. Chemistry{{See also|List of androgens/anabolic steroids}}Trenbolone, also known as 19-nor-δ9,11-testosterone or as estra-4,9,11-trien-17β-ol-3-one, is a synthetic estrane steroid a derivative of nandrolone (19-nortestosterone).[1][2][5] It is specifically nandrolone with two additional double bonds in the steroid nucleus.[1][2][5] Trenbolone esters, which have an ester at the C17β position, include trenbolone acetate, trenbolone enanthate, trenbolone hexahydrobenzylcarbonate, and trenbolone undecanoate.[1][2][5] HistoryTrenbolone was first synthesized in 1963.[17] Society and cultureGeneric namesTrenbolone is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}}.[1][2][3] It has also been referred to as trienolone or trienbolone.[1][2][3][18]Legal statusSome bodybuilders and athletes use trenbolone esters for their muscle-building and otherwise performance-enhancing effects.[5] Such use is illegal in the United States and many other countries, in Europe and Asia. The DEA classifies trenbolone and its esters as Schedule III controlled substances under the Controlled Substances Act.[19] Trenbolone is classified as a Schedule 4 drug in Canada[20] and a class C drug with no penalty for personal use or possession in the United Kingdom.[21] Use or possession of steroids without a prescription is a crime in Australia.[22] Doping in sports{{See also|List of doping in sport cases#Trenbolone esters}}There are known cases of doping in sports with trenbolone esters by professional athletes. References1. ^1 2 3 4 5 6 7 8 {{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|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3}} 2. ^1 2 3 4 5 6 7 8 {{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1636|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|page=1591}} 3. ^1 2 3 4 5 {{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=PA279|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=279–}} 4. ^https://www.drugs.com/international/trenbolone.html 5. ^1 2 3 4 5 6 7 8 9 10 11 12 {{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT618|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=491–499, 618–,724–}} 6. ^{{cite web | title = Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol)| url = http://www.depts.ttu.edu/afs/implantdb/dbhome/Revalor%20Tech%20Bulletin%2012.pdf | publisher = Merck Animal Health | last1 = Nichols | first1 = Wade | last2 = Hutcheson | first2 = John | last3 = Streeter | first3 = Marshall | last4 = Corrigan | first4 = Mark | last5 = Nuttelman | first5 = Brandon }} 7. ^{{cite journal|last1=Kicman|first1=A T|title=Pharmacology of anabolic steroids|journal=British Journal of Pharmacology|volume=154|issue=3|year=2008|pages=502–521|issn=0007-1188|doi=10.1038/bjp.2008.165|pmid=18500378|pmc=2439524}} 8. ^http://www.sportsci.org/encyc/anabster/anabster.html{{full citation needed|date=December 2012}} 9. ^{{cite journal |doi=10.1093/toxsci/70.2.202 |title=In Vitro and in Vivo Effects of 17beta-Trenbolone: A Feedlot Effluent Contaminant |year=2002 |last1=Wilson |first1=V. S. |journal=Toxicological Sciences |volume=70 |issue=2 |pages=202–11 |pmid=12441365 |last2=Lambright |first2=C |last3=Ostby |first3=J |last4=Gray Jr |first4=LE}} 10. ^{{cite journal |doi=10.1016/j.steroids.2010.01.019 |title=Tissue selectivity and potential clinical applications of trenbolone (17β-hydroxyestra-4,9,11-trien-3-one): A potent anabolic steroid with reduced androgenic and estrogenic activity |year=2010 |last1=Yarrow |first1=Joshua F. |last2=McCoy |first2=Sean C. |last3=Borst |first3=Stephen E. |journal=Steroids |volume=75 |issue=6 |pages=377–89 |pmid=20138077}} 11. ^{{cite journal |pmid=6361192 |year=1984 |last1=Gettys |first1=TW |last2=d'Occhio |first2=MJ |last3=Henricks |first3=DM |last4=Schanbacher |first4=BD |title=Suppression of LH secretion by oestradiol, dihydrotestosterone and trenbolone acetate in the acutely castrated bull |volume=100 |issue=1 |pages=107–12 |journal=The Journal of Endocrinology |doi=10.1677/joe.0.1000107}} 12. ^{{cite journal |first1=Tanveer |last1=Beg |first2=Yasir Hasan |last2=Siddique |first3=Mohammad |last3=Afzal |title=Chromosomal Damage Induced by Androgenic Anabolic Steroids, Stanozolol and Trenbolone, in Human Lymphocytes |journal=Advances in Environmental Biology |volume=1 |issue=1 |pages=39–43 |year=2007 |url=http://www.aensiweb.com/aeb/2007/39-43.pdf |deadurl=yes |archiveurl=https://web.archive.org/web/20130728190859/http://www.aensiweb.com/aeb/2007/39-43.pdf |archivedate=2013-07-28 |df= }} 13. ^1 {{cite book|author1=C. G. Nicholas Mascie-Taylor|author2=Lyliane Rosetta|title=Reproduction and Adaptation: Topics in Human Reproductive Ecology|url=https://books.google.com/books?id=7eVVK3vfAc0C&pg=PA69|date=13 January 2011|publisher=Cambridge University Press|isbn=978-1-139-49430-4|pages=69–}} 14. ^1 {{cite book|title=APMIS.: Supplementum|url=https://books.google.com/books?id=szFYAAAAYAAJ|year=2001|publisher=Munksgaard|page=5339}} 15. ^{{cite book|author=Kenneth W. McKerns|title=Reproductive Processes and Contraception|url=https://books.google.com/books?id=JM6oBwAAQBAJ&pg=PA171|date=13 March 2013|publisher=Springer Science & Business Media|isbn=978-1-4684-3824-6|pages=171–}} 16. ^{{cite journal |pmid=8674183 |year=1996 |last1=Schänzer |first1=W |title=Metabolism of anabolic androgenic steroids |volume=42 |issue=7 |pages=1001–20 |journal=Clinical Chemistry}} 17. ^{{cite journal | vauthors = Schänzer W | title = Metabolism of anabolic androgenic steroids | journal = Clin. Chem. | volume = 42 | issue = 7 | pages = 1001–20 | year = 1996 | pmid = 8674183 | doi = | url = }} 18. ^{{cite book|author=Food and Agriculture Organization of the United Nations|title=Residues of Some Veterinary Drugs in Animals and Foods: Monographs Prepared by the Thirty-Fourth Meeting of the Joint FAO/WHO Expert Committee on Food Additives, Geneva, 30 January-8 February 1989|url=https://books.google.com/books?id=BCw1OUlrT-QC&pg=PA88|year=1990|publisher=Food & Agriculture Org.|isbn=978-92-5-102933-6|pages=88–}} 19. ^{{cite web | title=Controlled Substances Act | url=http://www.fda.gov/regulatoryinformation/legislation/ucm148726.htm | publisher=United States Food and Drug Administration | date=11 June 2009 | accessdate=17 June 2016}} 20. ^http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-24.html?term=steroids#sched4 21. ^http://www.homeoffice.gov.uk/publications/alcohol-drugs/drugs/acmd1/anabolic-steroids-report/anabolic-steroids?view=Binary. 22. ^http://www.aic.gov.au/en/crime_types/drugs_alcohol/drug_types/steroids.aspx Further reading
External links{{Androgens and antiandrogens}}{{Progestogens and antiprogestogens}}{{Androgen receptor modulators}}{{Progesterone receptor modulators}} 6 : Alcohols|Androgens and anabolic steroids|Estranes|Ketones|Progestogens|World Anti-Doping Agency prohibited substances |
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