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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O2
Molecular Weight 270.3668
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRENBOLONE

SMILES

C[C@@]12C=CC3=C4CCC(=O)C=C4CC[C@@]3([H])[C@]2([H])CC[C@]1([H])O

InChI

InChIKey=MEHHPFQKXOUFFV-OWSLCNJRSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H22O2
Molecular Weight 270.3668
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment:: Known to be CNS penetrant in rat. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.15 nM [Kd]
53.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Finaplix®-H

Approved Use

Increases rate of weight gain and improves feed efficiency.

Launch Date

5.5209597E11
PubMed

PubMed

TitleDatePubMed
Fluctuating asymmetry and growth as biomarkers for exposure to androgen disrupting chemicals in Japanese quail.
2005 Aug
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.
2005 Dec 27
Evaluation of the rodent Hershberger bioassay using three reference (anti)androgens.
2005 Jun
Structural and functional diversity of microbial communities from a lake sediment contaminated with trenbolone, an endocrine-disrupting chemical.
2005 Sep
Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids.
2006
Identification of metabolites of trenbolone acetate in androgenic runoff from a beef feedlot.
2006 Apr
Introduction: The ecological relevance of chemically induced endocrine disruption in wildlife.
2006 Apr
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.
2006 Apr
[Rhabdomyolysis in a bodybuilder using steroids].
2006 May 13
Gene expression patterns in rainbow trout, Oncorhynchus mykiss, exposed to a suite of model toxicants.
2006 May 25
Modulation of steroidogenic gene expression and hormone production of H295R cells by pharmaceuticals and other environmentally active compounds.
2007 Dec 1
Reproductive toxicity of trenbolone acetate in embryonically exposed Japanese quail.
2007 Jan
Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry.
2007 Mar-Apr
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
Analysis of synthetic 19-norsteroids trenbolone, tetrahydrogestrinone and gestrinone by gas chromatography-mass spectrometry.
2007 May 25
In utero exposure to the environmental androgen trenbolone masculinizes female Sprague-Dawley rats.
2007 Nov 1
Evaluation of the rodent Hershberger bioassay: testing of coded chemicals and supplementary molecular-biological and biochemical investigations.
2007 Sep 24
Screening of in vitro synthesised metabolites of 4,9,11-trien-3-one steroids by liquid chromatography mass spectrometry.
2008
Induction of micronuclei in V79 cells by the anabolic doping steroids tetrahydrogestrinone and trenbolone.
2008 Apr
Chemical contaminants in feedlot wastes: concentrations, effects and attenuation.
2008 Aug
Identification of hormone esters in injection site in muscle tissues by LC/MS/MS.
2008 Dec
Intercalibration exercise using a stickleback endocrine disrupter screening assay.
2008 Feb
[Determination of three anabolic steroids by liquid chromatography-mass spectrometry].
2008 Jul
Effect of parental exposure to trenbolone and the brominated flame retardant BDE-47 on fertility in rainbow trout (Oncorhynchus mykiss).
2008 Jul
Confirmatory analysis of Trenbolone using accurate mass measurement with LC/TOF-MS.
2008 Jun 16
Comparison of estrogen-responsive plasma protein biomarkers and reproductive endpoints in sheepshead minnows exposed to 17beta-trenbolone.
2008 Jun 23
Trace analysis of androgens and progestogens in environmental waters by ultra-performance liquid chromatography-electrospray tandem mass spectrometry.
2008 Jun 27
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
[Determination of eleven steroid hormones in animal muscle tissues and eggs using ultra-performance liquid chromatography-tandem mass spectrometry].
2008 Nov
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008 Nov 28
Determination of trenbolone residual in bovine liver by liquid chromatography-mass spectrometry.
2009 Apr
Expression signatures for a model androgen and antiandrogen in the fathead minnow (Pimephales promelas) ovary.
2009 Apr 1
Stereoselective sorption by agricultural soils and liquid-liquid partitioning of trenbolone (17alpha and 17beta) and trendione.
2009 Dec 1
The watershed as a conceptual framework for the study of environmental and human health.
2009 Feb 18
Synthesis and SAR study of novel pseudo-steroids as potent and selective progesterone receptor antagonists.
2009 Jul 15
Doping control analysis of trenbolone and related compounds using liquid chromatography-tandem mass spectrometry.
2009 Mar
Confirmatory method for the determination of nandrolone and trenbolone in urine samples using immunoaffinity cleanup and liquid chromatography-tandem mass spectrometry.
2009 Nov 13
Analysis of anabolic steroids in hair: time courses in guinea pigs.
2009 Sep
Is the gonadotropin releasing hormone system vulnerable to endocrine disruption in birds?
2009 Sep 1
Hormonal growth promoting agents in food producing animals.
2010
Gonadal alterations in male eelpout (Zoarces viviparus) exposed to ethinylestradiol and trenbolone separately or in combination.
2010
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
Synthesis and characterization of new aromatic esters based on 4,16-pregnadiene-6,20-dione skeleton.
2010 Dec 8
Highly active human pharmaceuticals in aquatic systems: A concept for their identification based on their mode of action.
2010 Feb 18
Sex differences in the uptake and disposition of perfluorooctanoic acid in fathead minnows after oral dosing.
2010 Jan 1
Trenbolone causes irreversible masculinization of zebrafish at environmentally relevant concentrations.
2010 Jul 15
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
Soil temperature and moisture effects on the persistence of synthetic androgen 17alpha-trenbolone, 17beta-trenbolone and trendione.
2010 May
OECD validation of phase-3 Hershberger assay using the stimulated weanling male rat in Korea.
2010 May
Assessing the fate and transformation by-product potential of trenbolone during chlorination.
2010 Nov
Patents

Patents

Sample Use Guides

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 Sat Jun 26 08:20:40 UTC 2021
Edited
by admin
on Sat Jun 26 08:20:40 UTC 2021
Record UNII
P53R4420TR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRENBOLONE
INN   MI   WHO-DD  
INN  
Official Name English
TRENBOLONE [MI]
Common Name English
RU-2341
Code English
TRENBOLONE RELATED COMPOUND B
USP  
Common Name English
TRENBOLONE RELATED COMPOUND B [USP]
Common Name English
17BETA-TRENBOLONE
Common Name English
ESTRA-4,9,11-TRIEN-3-ONE, 17-HYDROXY-, (17.BETA.)-
Systematic Name English
TRIENBOLONE
Common Name English
TRENBOLONE [INN]
Common Name English
TRENBOLONE [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 556.739
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
NCI_THESAURUS C2360
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
DEA NO. 4000
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
Code System Code Type Description
INN
2916
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
EVMPD
SUB11232MIG
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
PUBCHEM
25015
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
RXCUI
1484278
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY RxNorm
FDA UNII
P53R4420TR
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
WIKIPEDIA
TRENBOLONE
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
MERCK INDEX
M11015
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY Merck Index
EPA CompTox
10161-33-8
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
DRUG BANK
DB11551
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
CAS
10161-33-8
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL1698011
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
NCI_THESAURUS
C95072
Created by admin on Sat Jun 26 08:20:41 UTC 2021 , Edited by admin on Sat Jun 26 08:20:41 UTC 2021
PRIMARY
Related Record Type Details
METABOLITE INACTIVE -> PARENT
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY