U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O3
Molecular Weight 312.4035
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 17.BETA.-HYDROXYESTRA-4,9,11-TRIEN-3-ONE, ACETATE

SMILES

CC(=O)O[C@@]1([H])CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CCC4=C3C=C[C@@]21C

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 312.4035
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
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.
2001 May
The fate of trenbolone acetate and melengestrol acetate after application as growth promoters in cattle: environmental studies.
2001 Nov
In vitro and in vivo effects of 17beta-trenbolone: a feedlot effluent contaminant.
2002 Dec
Determination of trenbolone and its metabolite in bovine fluids by liquid chromatography-tandem mass spectrometry.
2003 Jan 25
Testosterone-stimulated weanlings as an alternative to castrated male rats in the Hershberger anti-androgen assay.
2004 Apr
Enzyme-linked immunosorbent assay-based detection of free trenbolone in bovine bile.
2004 Jul 14
Mobility of the growth promoters trenbolone and melengestrol acetate in agricultural soil: column studies.
2004 Jun 29
Androgenic and estrogenic activity in water bodies receiving cattle feedlot effluent in Eastern Nebraska, USA.
2004 Mar
Tetrahydrogestrinone is a potent androgen and progestin.
2004 May
IGF-I mRNA levels in bovine satellite cell cultures: effects of fusion and anabolic steroid treatment.
2004 Nov
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.
2005 Apr 29
Evaluation of the rodent Hershberger bioassay using three reference (anti)androgens.
2005 Jun
Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids.
2006
Introduction: The ecological relevance of chemically induced endocrine disruption in wildlife.
2006 Apr
Rapid screening of doping agents in human urine by vacuum MALDI-linear ion trap mass spectrometry.
2007 Aug 1
Modulation of steroidogenic gene expression and hormone production of H295R cells by pharmaceuticals and other environmentally active compounds.
2007 Dec 1
Immunotoxicity of trenbolone acetate in Japanese quail.
2007 Jan
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
Evaluation of the rodent Hershberger bioassay: testing of coded chemicals and supplementary molecular-biological and biochemical investigations.
2007 Sep 24
Induction of micronuclei in V79 cells by the anabolic doping steroids tetrahydrogestrinone and trenbolone.
2008 Apr
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
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
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
Analysis of anabolic steroids in hair: time courses in guinea pigs.
2009 Sep
Hormonal growth promoting agents in food producing animals.
2010
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
Soil temperature and moisture effects on the persistence of synthetic androgen 17alpha-trenbolone, 17beta-trenbolone and trendione.
2010 May
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 Fri Jun 25 20:53:00 UTC 2021
Edited
by admin
on Fri Jun 25 20:53:00 UTC 2021
Record UNII
RUD5Y4SV0S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
17.BETA.-HYDROXYESTRA-4,9,11-TRIEN-3-ONE, ACETATE
Common 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
TRENBOLONE ACETATE [USP MONOGRAPH]
Common Name English
TRENBOLONE ACETATE [GREEN BOOK]
Common Name English
TRENBOLONE ACETATE [USP]
Common Name English
TRENBOLONE ACETATE CIII
USP-RS  
Common Name English
TRENBOLONE ACETATE [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.2476
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
CFR 21 CFR 522.2477
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
CFR 21 CFR 522.2478
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
NCI_THESAURUS C2360
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
Code System Code Type Description
PUBCHEM
66359
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
EPA CompTox
10161-34-9
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
CAS
10161-34-9
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
DRUG BANK
DB14660
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
WIKIPEDIA
Trenbolone acetate
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
NCI_THESAURUS
C61982
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
ECHA (EC/EINECS)
233-432-5
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
MERCK INDEX
M11015
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1698011
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
RXCUI
1484277
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1673828
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY USP-RS
FDA UNII
RUD5Y4SV0S
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
MESH
D014204
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
EVMPD
SUB32683
Created by admin on Fri Jun 25 20:53:00 UTC 2021 , Edited by admin on Fri Jun 25 20:53:00 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY