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Trenbolone

From Wikipedia, the free encyclopedia
Anabolic steroid
Not to be confused withTrestolone.

Pharmaceutical compound
Trenbolone
Clinical data
Other namesTrienolone; Trienbolone; RU-2341; Δ9,11-Nandrolone; 19-Nor-δ9,11-testosterone; Estra-4,9,11-trien-17β-ol-3-one
AHFS/Drugs.comInternational Drug Names
License data
Pregnancy
category
  • X
Routes of
administration
Intramuscular (asesters)
Drug classAndrogen;Anabolic steroid;Progestogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
BioavailabilityIMTooltip Intramuscular injection: 80-100%[citation needed]
MetabolismLiver
Eliminationhalf-life6–8 hours[citation needed]
ExcretionUrine
Identifiers
  • (8S,13S,14S,17S)-17-Hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.127.177Edit this at Wikidata
Chemical and physical data
FormulaC18H22O2
Molar mass270.372 g·mol−1
3D model (JSmol)
  • O=C4\C=C2/C(=C1/C=C\[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
  • InChI=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 checkY
  • Key:MEHHPFQKXOUFFV-OWSLCNJRSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Trenbolone is anandrogen andanabolic steroid (AAS) of thenandrolone group which itself was never marketed.[clarification needed][2][3][4][5][6]Trenbolone esterprodrugs, includingtrenbolone acetate (brand namesFinajet,Finaplix, others) andtrenbolone hexahydrobenzylcarbonate (brand namesParabolan,Hexabolan), are or have been marketed for veterinary and clinical use.[2][3][4][6][7][8] Trenbolone acetate is used inveterinary medicine inlivestock to increasemuscle growth andappetite, while trenbolone hexahydrobenzylcarbonate was formerly used clinically in humans but is now no longer marketed.[2][3][4][6] In addition, although it is not approved for clinical or veterinary use,trenbolone enanthate is sometimes sold on theblack market under the name trenabol.

A vial of injectabletrenbolone acetate.

Uses

[edit]

Veterinary

[edit]

Trenbolone, as trenbolone acetate, improves muscle mass, feed efficiency, and mineral absorption in cattle.[6]

Side effects

[edit]
See also:Anabolic steroid § Adverse effects

Sometimes human users may experience an event called "tren cough" shortly after or during an injection, where the user experiences a violent and extreme coughing fit, which can last for minutes and in some cases even longer.

"Tren cough", despite its name, is not exclusive to trenbolone. It can occur when injecting any oil-steroid solutions, if the solution accidentally is injected intravenously. When the oil-steroid solution gets into the bloodstream, the steroid oil solution travels into the lungs, therefore causing a coughing fit. There exist several theories on why this phenomenon happens.[9]

It is possible that the androgenic effect from steroids activates a variety of lipid-like active compounds which are calledprostaglandins.[10] Many of these prostaglandins are inflammatory and vasoconstrictive. Prostaglandins are signalled through two varying pathwayscyclooxygenase (COX) (Also known as:prostaglandin-endoperoxide synthase) andlipoxygenases (LOX) (also known as:EC 1.13.11.34,EC 1.13.11.33, etc.).[11] The bradykinin peptide is well known to promote a cough reaction associated withACE inhibitor medications prescribed forhypertension.[12]

Pharmacology

[edit]

Pharmacodynamics

[edit]

Trenbolone has bothanabolic andandrogenic effects.[6] Oncemetabolized, trenbolone esters have the effect of increasingammonium ion uptake by muscles, leading to an increase in the rate ofprotein synthesis. It may also have the secondary effects of stimulating appetite and decreasing the rate ofcatabolism, as allanabolic steroids are believed to; however, catabolism likely increases significantly once the steroid is no longer taken.[13] At least one study in rats has shown trenbolone to cause gene expression of theandrogen receptor (AR) at least as potent asdihydrotestosterone (DHT). This evidence tends to indicate trenbolone can cause an increase in malesecondary sex characteristics without the need to convert to a more potent androgen in the body.[14]

Studies on metabolism are mixed, with some studies showing that it is metabolized byaromatase intoestrogenic compounds, or by5α-reductase into 5α-reduced androgenic compounds.[15][16]

The potency of trenbolone is not known, although it's often falsely believed to be five times higher thantestosterone.[17][18] This is based on a book by William Llewellyn but has not been definitively proven. Trenbolone was never approved for human use, and therefore limited data on the subject exists. The relevant studies are usually done in rats, which makes the 500/100 potency number inaccurate. Rats respond differently and are less sensitive to androgens. While some literature report a 5 fold higher potency, two other scientific reviews report a 3 fold higher potency.[19][20] Trenbolone also binds with highaffinity to theprogesterone receptor,[6][21][22][23] and binds to theglucocorticoid receptor as well.[22]

Pharmacokinetics

[edit]

To prolong itselimination half-life, trenbolone is administered as aprodrug as anester conjugate such astrenbolone acetate,trenbolone enanthate, ortrenbolone hexahydrobenzylcarbonate.[2][3][4][6] Plasmalipases then cleave the ester group in the bloodstream leaving free trenbolone.[citation needed]

Trenbolone and 17-epitrenbolone are both excreted in urine as conjugates that can be hydrolyzed with beta-glucuronidase.[24] This implies that trenbolone leaves the body as beta-glucuronides orsulfates.

Chemistry

[edit]
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 asyntheticestranesteroid and aderivative ofnandrolone (19-nortestosterone).[2][3][6] It is specifically nandrolone with two additionaldouble bonds in the steroid nucleus.[2][3][6]Trenbolone esters, which have anester at the C17β position, includetrenbolone acetate,trenbolone enanthate,trenbolone hexahydrobenzylcarbonate, andtrenbolone undecanoate.[2][3][6][25]

Basic information about different types steroids included base trenbolone inside structure.
Name:TrenboloneTrenbolone acetateTrenbolone enanthateTrenbolone hexahydrobenzylcarbonate

(cyclohexylmethylcarbonate)

Structural[25]
FormulaC18H22O2C20H24O3C25H34O3C26H34O4
Crystal system[25]monocrystalicmonocrystalicmonocrystalic
Elimination half-life48–72 hours[citation needed]short

1–2 days;[25] 3 days[26]

long

11 days[25]

8 days[25]

History

[edit]

Trenbolone was firstsynthesized in 1963.[27]

Society and culture

[edit]

Generic names

[edit]

Trenbolone is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name andBANTooltip British Approved Name.[2][3][4] It has also been referred to astrienolone ortrienbolone or tren.[2][3][4][28]

Legal status

[edit]

Somebodybuilders andathletes use trenbolone hexahydrobenzylcarbonate and other esters (acetate, enanthate) for their muscle-building and otherwise performance-enhancing effects.[29][6] Such use is illegal in the United States and several European and Asian countries. The DEA classifies trenbolone and its esters asSchedule III controlled substances under theControlled Substances Act.[30] Trenbolone is classified as a Schedule 4 drug inCanada[31] and a class C drug with no penalty for personal use or possession in theUnited Kingdom.[32] Use or possession of steroids without a prescription is a crime inAustralia.[33]

Doping in sports

[edit]
See also:List of doping in sport cases § Trenbolone esters

There are known cases of doping in sports with trenbolone esters byprofessionalathletes.

Environmental persistence

[edit]

Early studies suggested that the metabolites of trenbolone acetate would degrade throughphototransformation. However, a 2013 paper found that theendocrine-disrupting metabolites were able to reform at night, resulting in a diurnal cycling of the compounds.[34] The environmental persistence of the steroid metabolites results in the contamination of water supplies and the disruption of aquatic reproductive processes. Due to its nocturnal reformation, researchers have referred to trenbolone as the "vampire steroid".[35][36]

See also

[edit]

References

[edit]
  1. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-15.
  2. ^abcdefghiElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer.ISBN 978-1-4757-2085-3.Archived from the original on 11 January 2023. Retrieved11 November 2017.
  3. ^abcdefghiIndex Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 1591.ISBN 978-3-88763-075-1.
  4. ^abcdefMorton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 279–.ISBN 978-94-011-4439-1.Archived from the original on 11 January 2023. Retrieved11 November 2017.
  5. ^"Trenbolone".Archived from the original on 2020-07-07. Retrieved2017-11-11.
  6. ^abcdefghijkLlewellyn W (2011).Anabolics. Molecular Nutrition Llc. pp. 491–499, 618–, 724–.ISBN 978-0-9828280-1-4.
  7. ^Nichols W, Hutcheson J, Streeter M, Corrigan M, Nuttelman B."Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol)"(PDF). Merck Animal Health.Archived(PDF) from the original on 2012-10-13. Retrieved2011-08-22.
  8. ^Kicman AT (June 2008)."Pharmacology of anabolic steroids".British Journal of Pharmacology.154 (3):502–521.doi:10.1038/bjp.2008.165.PMC 2439524.PMID 18500378.
  9. ^Russell M, Storck A, Ainslie M (2011)."Acute respiratory distress following intravenous injection of an oil-steroid solution".Canadian Respiratory Journal.18 (4):e59 –e61.doi:10.1155/2011/743151.PMC 3205107.PMID 22059184.
  10. ^Notelovitz M (April 2002)."Androgen effects on bone and muscle".Fertility and Sterility.77 (Suppl 4):S34 –S41.doi:10.1016/s0015-0282(02)02968-0.PMID 12007900.
  11. ^Kam PC, See AU (May 2000). "Cyclo-oxygenase isoenzymes: physiological and pharmacological role".Anaesthesia.55 (5):442–449.doi:10.1046/j.1365-2044.2000.01271.x.PMID 10792135.
  12. ^Fox AJ, Lalloo UG, Belvisi MG, Bernareggi M, Chung KF, Barnes PJ (July 1996). "Bradykinin-evoked sensitization of airway sensory nerves: a mechanism for ACE-inhibitor cough".Nature Medicine.2 (7):814–817.doi:10.1038/nm0796-814.PMID 8673930.
  13. ^Fahey TD (March 1998)."Anabolic Steroids: Mechanisms and Effects".Encyclopedia of sports medicine and science. Internet Society for Sport Science.Archived from the original on 2011-08-23. Retrieved2011-08-23.
  14. ^Wilson VS, Lambright C, Ostby J, Gray LE (December 2002)."In vitro and in vivo effects of 17beta-trenbolone: a feedlot effluent contaminant".Toxicological Sciences.70 (2):202–211.doi:10.1093/toxsci/70.2.202.PMID 12441365.
  15. ^Yarrow JF, McCoy SC, Borst SE (June 2010). "Tissue selectivity and potential clinical applications of trenbolone (17beta-hydroxyestra-4,9,11-trien-3-one): A potent anabolic steroid with reduced androgenic and estrogenic activity".Steroids.75 (6):377–389.doi:10.1016/j.steroids.2010.01.019.PMID 20138077.S2CID 205253265.
  16. ^Gettys TW, D'Occhio MJ, Henricks DM, Schanbacher BD (January 1984). "Suppression of LH secretion by oestradiol, dihydrotestosterone and trenbolone acetate in the acutely castrated bull".The Journal of Endocrinology.100 (1):107–112.doi:10.1677/joe.0.1000107.PMID 6361192.
  17. ^Llewellyn W (2011).Anabolics. Molecular Nutrition Llc.ISBN 978-0-9828280-1-4.
  18. ^Wiebe JP (2011-01-13)."The microenvironment in health and cancer of the mammary gland". In Mascie-Taylor CG, Rosetta L (eds.).Reproduction and Adaptation: Topics in Human Reproductive Ecology. Cambridge University Press. p. 69.ISBN 978-1-139-49430-4.
  19. ^Neumann F (1976). "Pharmacological and endocrinological studies on anabolic agents".Environmental Quality and Safety. Supplement (5):253–264.PMID 782871.
  20. ^Yarrow JF, McCoy SC, Borst SE (June 2010). "Tissue selectivity and potential clinical applications of trenbolone (17beta-hydroxyestra-4,9,11-trien-3-one): A potent anabolic steroid with reduced androgenic and estrogenic activity".Steroids.75 (6):377–389.doi:10.1016/j.steroids.2010.01.019.PMID 20138077.
  21. ^Nicholas Mascie-Taylor CG, Rosetta L (13 January 2011).Reproduction and Adaptation: Topics in Human Reproductive Ecology. Cambridge University Press. pp. 69–.ISBN 978-1-139-49430-4.
  22. ^abAPMIS.: Supplementum. Munksgaard. 2001. p. 5339.ISBN 9788716164575.
  23. ^McKerns KW (13 March 2013).Reproductive Processes and Contraception. Springer Science & Business Media. pp. 171–.ISBN 978-1-4684-3824-6.
  24. ^Schänzer W (July 1996)."Metabolism of anabolic androgenic steroids".Clinical Chemistry.42 (7):1001–1020.doi:10.1093/clinchem/42.7.1001.PMID 8674183.
  25. ^abcdefBorodi G, Turza A, Camarasan PA, Ulici A (2020). "Structural studies of Trenbolone, Trenbolone Acetate, Hexahydrobenzylcarbonate and Enanthate esters".Journal of Molecular Structure.1212 128127.Bibcode:2020JMoSt121228127B.doi:10.1016/j.molstruc.2020.128127.ISSN 0022-2860.S2CID 216299984.
  26. ^Ruiz P, Strain EC (2011).Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins.ISBN 978-1-60547-277-5.
  27. ^Schänzer W (July 1996)."Metabolism of anabolic androgenic steroids".Clinical Chemistry.42 (7):1001–1020.doi:10.1093/clinchem/42.7.1001.PMID 8674183.
  28. ^Food and Agriculture Organization of the United Nations (1990).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. Food & Agriculture Org. pp. 88–.ISBN 978-92-5-102933-6.
  29. ^"Trenbolone hexahydrobenzylcarbonate use in bodybuilding". 20 November 2021. Archived from the original on 24 November 2021. Retrieved24 November 2021.
  30. ^"Controlled Substances Act". United States Food and Drug Administration. 11 June 2009. Archived fromthe original on 2 March 2017. Retrieved17 June 2016.
  31. ^"Controlled Drugs and Substances Act".laws-lois.justice.gc.ca. Archived fromthe original on 2012-09-15.
  32. ^"Consideration of the Anabolic Steroids". London: Advisory Council on the Misuse of Drugs. September 2010. Archived fromthe original on 2011-09-22.
  33. ^"Australian Institute of Criminology - Steroids". Archived fromthe original on 2012-03-23. Retrieved2011-08-22.
  34. ^Qu S, Kolodziej EP, Long SA, Gloer JB, Patterson EV, Baltrusaitis J, et al. (October 2013)."Product-to-parent reversion of trenbolone: unrecognized risks for endocrine disruption".Science.342 (6156):347–351.doi:10.1126/science.1243192.PMC 4096139.PMID 24072818.
  35. ^"'Vampire Steroid' Could Threaten Water Supply: How Does Trenbolone Reawaken In The Absence Of Sunlight?".Medical Daily. September 27, 2013.
  36. ^Gravitz L (April 8, 2014)."'Vampire' Steroids Rise After Dark".Discover Magazine.

Further reading

[edit]
Androgens
(incl.AASTooltip anabolic–androgenic steroid)
ARTooltip Androgen receptoragonists
Progonadotropins
Antiandrogens
ARTooltip Androgen receptorantagonists
Steroidogenesis
inhibitors
5α-Reductase
Others
Antigonadotropins
Others
Progestogens
(andprogestins)
PRTooltip Progesterone receptoragonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptorantagonists
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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