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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H26O2
Molecular Weight 286.4093
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BOLDENONE

SMILES

C[C@@]12C=CC(=O)C=C2CC[C@@]3([H])[C@]4([H])CC[C@@]([H])([C@@]4(C)CC[C@@]31[H])O

InChI

InChIKey=RSIHSRDYCUFFLA-DYKIIFRCSA-N
InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-17,21H,3-6,8,10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H26O2
Molecular Weight 286.4093
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Boldenone (INN, BAN), also known as Δ1-testosterone, 1-dihydrotestosterone, or androsta-1,4-dien-3-one-17β-ol (train name Equipoise) is a long-acting injectable anabolic agent for horses, supplied in a vial providing 50 mg boldenone undecylenate per mL in sesame oil with 3% (w/v) benzyl alcohol as a preservative. The activity of boldenone is mainly anabolic, with a low androgenic potency. Boldenone will increase nitrogen retention, protein synthesis increases appetite and stimulates the release of erythropoietin in the kidneys. Boldenone was synthesized in an attempt to create a long-acting injectable methandrostenolone (Dianabol), for androgen deficiency disorders. Boldenone acts similar to methandrostenolone with fewer adverse androgenic effects. Although commonly compared to nandrolone, boldenone lacks progesterone receptor interaction and all the associated progestogenic side effects. Equipoise (Boldenone Undecylenate Injection) is recommended as an aid for treating debilitated horses when an improvement in weight, haircoat or general physical condition is desired. Debilitation often follows disease or may occur following overwork and overexertion. Boldenone improves the general state of debilitated horses, thus aiding in correcting weight losses and improving appetite. It is not a substitute for a well-balanced diet. Optimal results can be expected only when good management and feeding practices are utilized. Boldenone should be considered only as adjunctive therapy to other specific and supportive therapy for diseases, surgical cases, and traumatic injuries.

Originator

Curator's Comment:: # Pfizer & Co C

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Equipoise

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids.
2006
Criteria to distinguish between natural situations and illegal use of boldenone, boldenone esters and boldione in cattle 1. Metabolite profiles of boldenone, boldenone esters and boldione in cattle urine.
2006 Dec
Pharmacokinetics of boldenone and stanozolol and the results of quantification of anabolic and androgenic steroids in race horses and nonrace horses.
2007 Apr
Analysis of anabolic steroids in hair by GC/MS/MS.
2007 Apr
Excretion profile of boldenone and its metabolites after oral administration to veal calves.
2007 Apr 25
Rapid screening of doping agents in human urine by vacuum MALDI-linear ion trap mass spectrometry.
2007 Aug 1
Androgen receptor or estrogen receptor-beta blockade alters DHEA-, DHT-, and E(2)-induced proliferation and PSA production in human prostate cancer cells.
2007 Aug 1
Development of an immunosensor for the detection of testosterone in bovine urine.
2007 Jan 30
Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted.
2007 Jul
Effects of steroidal and non-steroidal antiandrogens on wild-type and mutant androgen receptors.
2007 Jun 1
Survey of nutritional supplements for selected illegal anabolic steroids and ephedrine using LC-MS/MS and GC-MS methods, respectively.
2007 Mar
An in vitro study on metabolism of 17beta-boldenone and boldione using cattle liver and kidney subcellular fractions.
2007 Mar 14
Excretion profile of boldenone in urine of veal calves fed two different milk replacers.
2007 Mar 14
Formation of boldenone and boldenone-analogues by maggots of Lucilia sericata.
2007 Mar 14
Development and validation of a liquid chromatography-tandem mass spectrometry method for the separation of conjugated and unconjugated 17alpha- and 17beta-boldenone in urine sample.
2007 Mar 14
Development of a method which discriminates between endogenous and exogenous beta-boldenone.
2007 Mar 14
Phytosterols and anabolic agents versus designer drugs.
2007 Mar 14
The ultimate veal calf reference experiment: hormone residue analysis data obtained by gas and liquid chromatography tandem mass spectrometry.
2007 Mar 14
Pathology of the testicle and sex accessory glands following the administration of boldenone and boldione as growth promoters in veal calves.
2007 Nov
A new highly specific and robust yeast androgen bioassay for the detection of agonists and antagonists.
2007 Nov
Determination of anabolic steroids in muscle tissue by liquid chromatography-tandem mass spectrometry.
2007 Oct 17
Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites.
2007 Oct 3
Integrated analytical approach in veal calves administered the anabolic androgenic steroids boldenone and boldione: urine and plasma kinetic profile and changes in plasma protein expression.
2007 Sep
In vitro and in vivo effects of bicalutamide on the expression of TrkA and P75 neurotrophin receptors in prostate carcinoma.
2007 Sep 1
Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry.
2008
Fractionation of free and conjugated steroids for the detection of boldenone metabolites in calf urine with ultra-performance liquid chromatography/tandem mass spectrometry.
2008 Aug
Nonlinear immunofluorescent assay for androgenic hormones based on resonant structures.
2008 Aug 18
Mitochondrial redox signaling by p66Shc is involved in regulating androgenic growth stimulation of human prostate cancer cells.
2008 Aug 28
Androgen resistance in prostate cancer.
2008 Jan 15
Nutritional supplements cross-contaminated and faked with doping substances.
2008 Jul
Boldenone, testosterone and 1,4-androstadiene-3,17-dione determination in faeces from horses, untreated and after administration of androsta-1,4-diene-3,17-dione (boldione).
2008 Jun
Liquid chromatographic method development for anabolic androgenic steroids using a monolithic column Application to animal feed samples.
2008 Mar 17
Multivariate optimization of a derivatisation procedure for the simultaneous determination of nine anabolic steroids by gas chromatography coupled with mass spectrometry.
2008 May 9
[Determination of eleven steroid hormones in animal muscle tissues and eggs using ultra-performance liquid chromatography-tandem mass spectrometry].
2008 Nov
Cytogenetic and clinical studies of a male infant with disorder of sexual development: case report.
2008 Nov
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008 Nov 28
Quantification of 19-nortestosterone sulphate and boldenone sulphate in urine from male horses using liquid chromatography/tandem mass spectrometry.
2008 Oct
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
2008 Sep
Simultaneous measurement of boldenone (alpha and beta), ADD, testosterone, epitestosterone and AED in bovine faeces.
2008 Sep
Acupuncture and exercise restore adipose tissue expression of sympathetic markers and improve ovarian morphology in rats with dihydrotestosterone-induced PCOS.
2009 Apr
Validation and application of a yeast bioassay for screening androgenic activity in calf urine and feed.
2009 Apr 1
Bicalutamide demonstrates biologic effectiveness in prostate cancer cell lines and tumor primary cultures irrespective of Her2/neu expression levels.
2009 Aug
17alpha- and 17beta-boldenone 17-glucuronides: synthesis and complete characterization by 1H and 13C NMR.
2009 Feb
Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control.
2009 Jan
Evaluation of equine urine reactivity towards phase II metabolites of 17-hydroxy steroids by liquid chromatography/tandem mass spectrometry.
2009 Jan
Characterization of SV-40 Tag rats as a model to study prostate cancer.
2009 Jan 26
Sudden unexpected death in a female fitness athlete, with a possible connection to the use of anabolic androgenic steroids (AAS) and ephedrine.
2009 Jan 30
The risk of hepatotoxicity during long-term and low-dose flutamide treatment in hirsutism.
2009 Mar
Criteria to distinguish between natural situations and illegal use of boldenone, boldenone esters and boldione in cattle 2. Direct measurement of 17beta-boldenone sulpho-conjugate in calf urine by liquid chromatography--high resolution and tandem mass spectrometry.
2009 Oct
Analysis of anabolic steroids in hair: time courses in guinea pigs.
2009 Sep
Patents

Sample Use Guides

In Vivo Use Guide
The dosage for horses is 0.5 mg per pound of body weight intramuscularly. Treatment may be repeated at three week intervals.
Route of Administration: Intramuscular
The rhAR preparation was diluted 150 in assay buffer (5 mM Na2HP04, 150 mM NaCl, pH 7.2, containing 0.16% w/v protease inhibitor mix and 0.1% bovine serum albumin). Aliquots of 0.5 mL were incubated at 04°C for 16 hours with a constant amount of 0.4 nM 3H-DHT and in the presence or absence of increasing concentrations of Boldenone . DHT was used in all experiments as standard. To separate bound and free ligand, the receptor preparation was incubated with 100 mkL of dextrancoated charcoal (4%) charcoal and 0.4% dextran in assay buffer) for 5 min before centrifugation at 2000 x g for 15 min at 4°C. 0.4 mL of the supernatant was transferred into scintillation vials, mixed with 3 mL Xylofluor and counted. Specific binding represents the relative difference of total binding and non specific binding observed in the presence of a 250 fold surplus of unlabelled DHT.
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:52:52 UTC 2021
Edited
by admin
on Sat Jun 26 03:52:52 UTC 2021
Record UNII
5H7I2IP58X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BOLDENONE
INN   MI  
INN  
Official Name English
NSC-79102
Code English
TESTOSTERONE IMPURITY H [EP]
Common Name English
BOLDENONE [INN]
Common Name English
BOLDENONE [MI]
Common Name English
PARENABOL
Brand Name English
VEBONOL
Brand Name English
DEHYDROTESTOSTERONE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.204
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
NCI_THESAURUS C2360
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
DEA NO. 4000
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
Code System Code Type Description
FDA UNII
5H7I2IP58X
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
WIKIPEDIA
BOLDENONE
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
CAS
846-48-0
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
PUBCHEM
13308
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL2106059
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
DRUG BANK
DB01541
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
INN
2464
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
EVMPD
SUB05869MIG
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
MERCK INDEX
M2597
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
212-686-0
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
MESH
C013915
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
NCI_THESAURUS
C75064
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
RXCUI
2289408
Created by admin on Sat Jun 26 03:52:52 UTC 2021 , Edited by admin on Sat Jun 26 03:52:52 UTC 2021
PRIMARY
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY