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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H26O2
Molecular Weight 286.4085
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BOLDENONE

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2O

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 286.4085
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim
PubMed

PubMed

TitleDatePubMed
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.
2009-10
Analysis of anabolic steroids in hair: time courses in guinea pigs.
2009-09
Bicalutamide demonstrates biologic effectiveness in prostate cancer cell lines and tumor primary cultures irrespective of Her2/neu expression levels.
2009-08
Validation and application of a yeast bioassay for screening androgenic activity in calf urine and feed.
2009-04-01
Acupuncture and exercise restore adipose tissue expression of sympathetic markers and improve ovarian morphology in rats with dihydrotestosterone-induced PCOS.
2009-04
The risk of hepatotoxicity during long-term and low-dose flutamide treatment in hirsutism.
2009-03
17alpha- and 17beta-boldenone 17-glucuronides: synthesis and complete characterization by 1H and 13C NMR.
2009-02
Sudden unexpected death in a female fitness athlete, with a possible connection to the use of anabolic androgenic steroids (AAS) and ephedrine.
2009-01-30
Characterization of SV-40 Tag rats as a model to study prostate cancer.
2009-01-26
Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control.
2009-01
Evaluation of equine urine reactivity towards phase II metabolites of 17-hydroxy steroids by liquid chromatography/tandem mass spectrometry.
2009-01
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008-11-28
[Determination of eleven steroid hormones in animal muscle tissues and eggs using ultra-performance liquid chromatography-tandem mass spectrometry].
2008-11
Cytogenetic and clinical studies of a male infant with disorder of sexual development: case report.
2008-11
Quantification of 19-nortestosterone sulphate and boldenone sulphate in urine from male horses using liquid chromatography/tandem mass spectrometry.
2008-10
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
2008-09
Simultaneous measurement of boldenone (alpha and beta), ADD, testosterone, epitestosterone and AED in bovine faeces.
2008-09
Mitochondrial redox signaling by p66Shc is involved in regulating androgenic growth stimulation of human prostate cancer cells.
2008-08-28
Nonlinear immunofluorescent assay for androgenic hormones based on resonant structures.
2008-08-18
Fractionation of free and conjugated steroids for the detection of boldenone metabolites in calf urine with ultra-performance liquid chromatography/tandem mass spectrometry.
2008-08
Nutritional supplements cross-contaminated and faked with doping substances.
2008-07
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).
2008-06
Multivariate optimization of a derivatisation procedure for the simultaneous determination of nine anabolic steroids by gas chromatography coupled with mass spectrometry.
2008-05-09
Liquid chromatographic method development for anabolic androgenic steroids using a monolithic column Application to animal feed samples.
2008-03-17
Androgen resistance in prostate cancer.
2008-01-15
Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry.
2008
Pathology of the testicle and sex accessory glands following the administration of boldenone and boldione as growth promoters in veal calves.
2007-11
A new highly specific and robust yeast androgen bioassay for the detection of agonists and antagonists.
2007-11
Determination of anabolic steroids in muscle tissue by liquid chromatography-tandem mass spectrometry.
2007-10-17
Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites.
2007-10-03
In vitro and in vivo effects of bicalutamide on the expression of TrkA and P75 neurotrophin receptors in prostate carcinoma.
2007-09-01
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.
2007-09
Rapid screening of doping agents in human urine by vacuum MALDI-linear ion trap mass spectrometry.
2007-08-01
Androgen receptor or estrogen receptor-beta blockade alters DHEA-, DHT-, and E(2)-induced proliferation and PSA production in human prostate cancer cells.
2007-08-01
Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted.
2007-07
Effects of steroidal and non-steroidal antiandrogens on wild-type and mutant androgen receptors.
2007-06-01
Excretion profile of boldenone and its metabolites after oral administration to veal calves.
2007-04-25
Pharmacokinetics of boldenone and stanozolol and the results of quantification of anabolic and androgenic steroids in race horses and nonrace horses.
2007-04
Analysis of anabolic steroids in hair by GC/MS/MS.
2007-04
An in vitro study on metabolism of 17beta-boldenone and boldione using cattle liver and kidney subcellular fractions.
2007-03-14
Excretion profile of boldenone in urine of veal calves fed two different milk replacers.
2007-03-14
Formation of boldenone and boldenone-analogues by maggots of Lucilia sericata.
2007-03-14
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.
2007-03-14
Development of a method which discriminates between endogenous and exogenous beta-boldenone.
2007-03-14
Phytosterols and anabolic agents versus designer drugs.
2007-03-14
The ultimate veal calf reference experiment: hormone residue analysis data obtained by gas and liquid chromatography tandem mass spectrometry.
2007-03-14
Survey of nutritional supplements for selected illegal anabolic steroids and ephedrine using LC-MS/MS and GC-MS methods, respectively.
2007-03
Development of an immunosensor for the detection of testosterone in bovine urine.
2007-01-30
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.
2006-12
Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids.
2006
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 Mon Mar 31 17:54:59 GMT 2025
Edited
by admin
on Mon Mar 31 17:54:59 GMT 2025
Record UNII
5H7I2IP58X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PARENABOL
Preferred Name English
BOLDENONE
INN   MI  
INN  
Official Name English
Boldenone [WHO-DD]
Common Name English
NSC-79102
Code English
boldenone [INN]
Common Name English
TESTOSTERONE IMPURITY H [EP IMPURITY]
Common Name English
BOLDENONE [MI]
Common Name English
VEBONOL
Brand Name English
DEHYDROTESTOSTERONE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.204
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
WIKIPEDIA Designer-drugs-Boldenone
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
NCI_THESAURUS C2360
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
DEA NO. 4000
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
Code System Code Type Description
NSC
79102
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
FDA UNII
5H7I2IP58X
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
WIKIPEDIA
BOLDENONE
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
CAS
846-48-0
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
PUBCHEM
13308
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
ChEMBL
CHEMBL2106059
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
DRUG BANK
DB01541
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
INN
2464
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
EVMPD
SUB05869MIG
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
MERCK INDEX
m2597
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID20894201
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
CHEBI
34584
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
ECHA (EC/EINECS)
212-686-0
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
MESH
C013915
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
SMS_ID
100000086347
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
NCI_THESAURUS
C75064
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
PRIMARY
RXCUI
2289408
Created by admin on Mon Mar 31 17:54:59 GMT 2025 , Edited by admin on Mon Mar 31 17:54:59 GMT 2025
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