TRENBOLONE ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24O3
Molecular Weight	312.4028
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@H](OC(C)=O)[C@@]1(C)C=CC3=C4CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=CMRJPMODSSEAPL-FYQPLNBISA-N

InChI=1S/C20H24O3/c1-12(21)23-19-8-7-18-17-5-3-13-11-14(22)4-6-15(13)16(17)9-10-20(18,19)2/h9-11,17-19H,3-8H2,1-2H3/t17-,18+,19+,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H24O3
Molecular Weight	312.4028
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://animaldrugsatfda.fda.gov/adafda/app/search/public/document/downloadFoi/221
Curator's Comment: description was created based on several sources, including: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=de1d618f-7e27-4307-9330-0e1a2255ee95 http://www.wikidoc.org/index.php/Trenbolone

Trenbolone is an anabolic steroid. It is used on livestock to increase muscle growth and appetite. Trenbolone compounds have a binding affinity for the androgen receptor three times as high as that of testosterone. Once metabolized, the drugs have the effect of increasing nitrogen uptake by muscles, leading to an increase in the rate of protein synthesis. It also has the secondary effects of stimulating appetite, reducing the amount of fat being deposited in the body, and decreasing the rate of catabolism. Short-term side effects include insomnia, high blood pressure, increased aggression, night sweats, and libido.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11252818	Binding Agent 1064	0.15 nM [Kd]
Progesterone receptor 61 Target ID: CHEMBL208 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11252818	Binding Agent 1064
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3486322	Binding Agent 1064	53.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Weight gain 4 Sources: http://www.accessdata.fda.gov/spl/data/d1f62758-6d8f-40df-8e6c-d7377f1fbd1e/d1f62758-6d8f-40df-8e6c-d7377f1fbd1e.xml	Primary		Approved 8429	Finaplix®-H Approved Use Increases rate of weight gain and improves feed efficiency. Launch Date 1987

PubMed

Title	Date	PubMed
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.	2005 Dec 27	16289956
Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids.	2006	16862626
Application of ecotoxicogenomics for studying endocrine disruption in vertebrates and invertebrates.	2006 Apr	16818254
Introduction: The ecological relevance of chemically induced endocrine disruption in wildlife.	2006 Apr	16818239
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.	2006 Apr	16488153
Doping control analysis in human urine by liquid chromatography-electrospray ionization ion trap mass spectrometry for the Olympic Games Athens 2004: determination of corticosteroids and quantification of ephedrines, salbutamol and morphine.	2006 Jul 28	17723530
[Rhabdomyolysis in a bodybuilder using steroids].	2006 May 13	16733985
Rapid screening of doping agents in human urine by vacuum MALDI-linear ion trap mass spectrometry.	2007 Aug 1	17602668
Modulation of steroidogenic gene expression and hormone production of H295R cells by pharmaceuticals and other environmentally active compounds.	2007 Dec 1	17822730
The OECD program to validate the rat Hershberger bioassay to screen compounds for in vivo androgen and antiandrogen responses: phase 2 dose-response studies.	2007 May	17520051
In utero exposure to the environmental androgen trenbolone masculinizes female Sprague-Dawley rats.	2007 Nov 1	17931805
A league of their own: demographics, motivations and patterns of use of 1,955 male adult non-medical anabolic steroid users in the United States.	2007 Oct 11	17931410
Determination of anabolic steroids in muscle tissue by liquid chromatography-tandem mass spectrometry.	2007 Oct 17	17887801
Evaluation of the rodent Hershberger bioassay: testing of coded chemicals and supplementary molecular-biological and biochemical investigations.	2007 Sep 24	17688994
Screening of in vitro synthesised metabolites of 4,9,11-trien-3-one steroids by liquid chromatography mass spectrometry.	2008	18708698
Induction of micronuclei in V79 cells by the anabolic doping steroids tetrahydrogestrinone and trenbolone.	2008 Apr	17764006
Chemical contaminants in feedlot wastes: concentrations, effects and attenuation.	2008 Aug	18055014
Identification of hormone esters in injection site in muscle tissues by LC/MS/MS.	2008 Dec	19680861
Intercalibration exercise using a stickleback endocrine disrupter screening assay.	2008 Feb	18348632
[Determination of three anabolic steroids by liquid chromatography-mass spectrometry].	2008 Jul	18959243
Effect of parental exposure to trenbolone and the brominated flame retardant BDE-47 on fertility in rainbow trout (Oncorhynchus mykiss).	2008 Jul	18397801
Confirmatory analysis of Trenbolone using accurate mass measurement with LC/TOF-MS.	2008 Jun 16	18501249
Comparison of estrogen-responsive plasma protein biomarkers and reproductive endpoints in sheepshead minnows exposed to 17beta-trenbolone.	2008 Jun 23	18495259
Trace analysis of androgens and progestogens in environmental waters by ultra-performance liquid chromatography-electrospray tandem mass spectrometry.	2008 Jun 27	18502434
The detection and assessment of the aneugenic potential of selected oestrogens, progestins and androgens using the in vitro cytokinesis blocked micronucleus assay.	2008 Mar 12	18069048
Degradation of synthetic androgens 17alpha- and 17beta-trenbolone and trendione in agricultural soils.	2008 May 15	18546691
Distribution of trenbolone residues in liver and various muscle groups of heifers that received multiple implants at the recommended site of application.	2008 May-Jun	18567315
[Determination of eleven steroid hormones in animal muscle tissues and eggs using ultra-performance liquid chromatography-tandem mass spectrometry].	2008 Nov	19253550
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.	2008 Nov 28	19040748
Determination of trenbolone residual in bovine liver by liquid chromatography-mass spectrometry.	2009 Apr	18953471
Expression signatures for a model androgen and antiandrogen in the fathead minnow (Pimephales promelas) ovary.	2009 Apr 1	19452925
Stereoselective sorption by agricultural soils and liquid-liquid partitioning of trenbolone (17alpha and 17beta) and trendione.	2009 Dec 1	19943653
The watershed as a conceptual framework for the study of environmental and human health.	2009 Feb 18	20508751
Synthesis and SAR study of novel pseudo-steroids as potent and selective progesterone receptor antagonists.	2009 Jul 15	19217285
Doping control analysis of trenbolone and related compounds using liquid chromatography-tandem mass spectrometry.	2009 Mar	19007801
Confirmatory method for the determination of nandrolone and trenbolone in urine samples using immunoaffinity cleanup and liquid chromatography-tandem mass spectrometry.	2009 Nov 13	19447393
Analysis of anabolic steroids in hair: time courses in guinea pigs.	2009 Sep	19397917
Is the gonadotropin releasing hormone system vulnerable to endocrine disruption in birds?	2009 Sep 1	19457435
Hormonal growth promoting agents in food producing animals.	2010	20020373
Gonadal alterations in male eelpout (Zoarces viviparus) exposed to ethinylestradiol and trenbolone separately or in combination.	2010	19864016
In vitro study of Organization for Economic Co-operation and Development (OECD) endocrine disruptor screening and testing methods- establishment of a recombinant rat androgen receptor (rrAR) binding assay.	2010 Apr	20371976
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.	2010 Apr	20155493
Synthesis and characterization of new aromatic esters based on 4,16-pregnadiene-6,20-dione skeleton.	2010 Dec 8	21143843
Highly active human pharmaceuticals in aquatic systems: A concept for their identification based on their mode of action.	2010 Feb 18	20053463
Sex differences in the uptake and disposition of perfluorooctanoic acid in fathead minnows after oral dosing.	2010 Jan 1	19961202
Trenbolone causes irreversible masculinization of zebrafish at environmentally relevant concentrations.	2010 Jul 15	20363039
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.	2010 Jun	20138077
Soil temperature and moisture effects on the persistence of synthetic androgen 17alpha-trenbolone, 17beta-trenbolone and trendione.	2010 May	20231030
OECD validation of phase-3 Hershberger assay using the stimulated weanling male rat in Korea.	2010 May	20082360
Assessing the fate and transformation by-product potential of trenbolone during chlorination.	2010 Nov	20719355

Patents

Sample Use Guides

In Vivo Use Guide

One implant containing 200 mg trenbolone acetate is administered to each animal. The implant is placed under the skin on the posterior aspect of the ear by means of a special implanter.

Route of Administration: Other

In Vitro Use Guide

Trenbolone was a high-affinity ligand for the androgen receptor (AR), with an IC(50) of about 4 nM in rat ventral prostate cytosol and about 33 nM in cells transfected with the human AR.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:16:01 GMT 2023` Edited by `admin` on `Fri Dec 15 16:16:01 GMT 2023`
Record UNII	RUD5Y4SV0S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRENBOLONE ACETATE

Official Name

English

TRENBOLONE ACETATE CIII [USP-RS]

Common Name

English

TRENBOLONE ACETATE [MI]

Common Name

English

TRENBOLONE ACETATE [USAN]

Common Name

English

TRENBOLONE ACETATE [MART.]

Common Name

English

ESTRA-4,9,11-TRIEN-3-ONE, 17-(ACETYLOXY)-, (17.BETA.)-

Systematic Name

English

RU-1697

Code

English

17β-Hydroxyestra-4,9,11-trien-3-one, acetate

Common Name

English

TRENBOLONE ACETATE [USP MONOGRAPH]

Common Name

English

Trenbolone acetate [WHO-DD]

Common Name

English

TRENBOLONE ACETATE [GREEN BOOK]

Common Name

English

TRENBOLONE ACETATE [USP IMPURITY]

Common Name

English

TRENBOLONE ACETATE CIII

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.2476