Trendione

{{Short description|Chemical compound}}

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| IUPAC_name = (8S,13S,14S)-13-Methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione

| image = Trendione.svg

| width = 200px

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| class = Androgen; Anabolic steroid; Progestogen

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| CAS_number = 4642-95-9

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| PubChem = 160762

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| ChemSpiderID = 141254

| UNII = 7M9J4CV848

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| synonyms = RU-2065; Trenavar; Triendione; Estra-4,9,11-triene-3,17-dione

| C=18 | H=20 | O=2

| SMILES = C[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CCC2=O

| StdInChI_Ref =

| StdInChI = 1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h8-10,15-16H,2-7H2,1H3/t15-,16+,18+/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = KBSXJBBFQODDTQ-RYRKJORJSA-N

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Trendione (developmental code name RU-2065; nickname Trenavar), also known as estra-4,9,11-triene-3,17-dione, is an androgen prohormone as well as metabolite of the anabolic steroid trenbolone.{{cite journal | vauthors = Liane BJ, Magee C | title = Guerilla Warfare on the Pancreas? A Case of Acute Pancreatitis From a Supplement Known to Contain Anabolic-Androgenic Steroids | journal = Mil Med | volume = 181 | issue = 10 | pages = e1395–e1397 | date = October 2016 | pmid = 27753588 | doi = 10.7205/MILMED-D-15-00575 | doi-access = free }}{{cite journal | vauthors = Yarrow JF, McCoy SC, Borst SE | title = 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 | journal = Steroids | volume = 75 | issue = 6 | pages = 377–89 | date = June 2010 | pmid = 20138077 | doi = 10.1016/j.steroids.2010.01.019 | s2cid = 205253265 }}{{cite journal | vauthors = Metzler M | title = Metabolism of some anabolic agents: toxicological and analytical aspects | journal = J. Chromatogr. | volume = 489 | issue = 1 | pages = 11–21 | date = April 1989 | pmid = 2745641 | doi = 10.1016/s0378-4347(00)82880-7}}{{cite journal | vauthors = Yarrow JF, Conover CF, McCoy SC, Lipinska JA, Santillana CA, Hance JM, Cannady DF, VanPelt TD, Sanchez J, Conrad BP, Pingel JE, Wronski TJ, Borst SE | title = 17β-Hydroxyestra-4,9,11-trien-3-one (trenbolone) exhibits tissue selective anabolic activity: effects on muscle, bone, adiposity, hemoglobin, and prostate | journal = Am. J. Physiol. Endocrinol. Metab. | volume = 300 | issue = 4 | pages = E650–60 | date = April 2011 | pmid = 21266670 | doi = 10.1152/ajpendo.00440.2010 | pmc = 6189634 }}{{cite journal | vauthors = Spranger B, Metzler M | title = Disposition of 17 beta-trenbolone in humans | journal = J. Chromatogr. | volume = 564 | issue = 2 | pages = 485–92 | date = April 1991 | pmid = 1874853 | doi = 10.1016/0378-4347(91)80517-g}} Trendione is to trenbolone as androstenedione is to testosterone.{{cite book|title=Advances in Agronomy|url=https://books.google.com/books?id=ydh79BFwCnoC&pg=PA16|date=13 April 2007|publisher=Elsevier|isbn=978-0-08-048819-6|pages=16–}} The compound is inactive itself, showing more than 100-fold lower affinity for the androgen and progesterone receptors than trenbolone.{{cite journal | vauthors = Bauer ER, Daxenberger A, Petri T, Sauerwein H, Meyer HH | title = Characterisation of the affinity of different anabolics and synthetic hormones to the human androgen receptor, human sex hormone binding globulin and to the bovine progestin receptor | journal = APMIS | volume = 108 | issue = 12 | pages = 838–46 | date = December 2000 | pmid = 11252818 | doi = 10.1111/j.1600-0463.2000.tb00007.x| s2cid = 22776408 }}{{cite journal | vauthors = Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP | title = Steroid flexibility and receptor specificity | journal = J. Steroid Biochem. | volume = 13 | issue = 1 | pages = 45–59 | date = January 1980 | pmid = 7382482 | doi = 10.1016/0022-4731(80)90112-0 }} It is a designer steroid and has been sold on the internet as a "nutritional supplement". Trendione is listed in the United States Designer Anabolic Steroid Control Act of 2014.