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

Details

Stereochemistry ABSOLUTE
Molecular Formula C30H44O3
Molecular Weight 452.6686
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BOLDENONE UNDECYLENATE

SMILES

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

InChI

InChIKey=AHMMSNQYOPMLSX-CNQKSJKFSA-N
InChI=1S/C30H44O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h4,17,19,21,24-27H,1,5-16,18,20H2,2-3H3/t24-,25-,26-,27-,29-,30-/m0/s1

HIDE SMILES / InChI
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
Regulation of the epididymal glutathione peroxidase-like protein in the mouse: dependence upon androgens and testicular factors.
1992 Nov
Transformations of testosterone and related steroids in Absidia glauca culture.
2003
A new bacterial steroid degradation gene cluster in Comamonas testosteroni TA441 which consists of aromatic-compound degradation genes for seco-steroids and 3-ketosteroid dehydrogenase genes.
2003 Aug
Transformations of testosterone and related steroids by Botrytis cinerea.
2003 Jan
Dihydrotestesterone induction of EPHB2 expression in the female genital tubercle mimics male pattern of expression during embryogenesis.
2003 Oct
Biotransformation of (+)-androst-4-ene-3,17-dione.
2004 Dec
Histopathological effects of boldenone in cattle.
2004 Mar
Complete 1H and 13C NMR spectral assignment of 17-hydroxy epimeric sterols with planar A or A and B rings.
2004 Mar
Confirmatory analysis of 17beta-boldenone, 17alpha-boldenone and androsta-1,4-diene-3,17-dione in bovine urine, faeces, feed and skin swab samples by liquid chromatography-electrospray ionisation tandem mass spectrometry.
2004 Mar 5
Production of androgens by microbial transformation of progesterone in vitro: a model for androgen production in rivers.
2004 Nov
Fetal alcohol exposure alters neurosteroid levels in the developing rat brain.
2004 Sep
Detection of endogenous boldenone in the entire male horses.
2004 Sep 5
ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results.
2005 Aug
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.
2005 Dec 27
Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.
2005 Sep 8
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.
2006 Apr
17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties.
2006 Aug 20
Neoformation of boldenone and related steroids in faeces of veal calves.
2006 Feb
Dehydroepiandrosterone decreases while cortisol increases in vitro growth and viability of Entamoeba histolytica.
2006 Feb
Effects of chronic exposure to sodium arsenite on hypothalamo-pituitary-testicular activities in adult rats: possible an estrogenic mode of action.
2006 Feb 16
Winter profile of plasma sex steroid levels in free-living male western diamond-backed rattlesnakes, Crotalus atrox (Serpentes: Viperidae).
2006 Oct
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
Formation of boldenone and boldenone-analogues by maggots of Lucilia sericata.
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
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
Mitochondrial redox signaling by p66Shc is involved in regulating androgenic growth stimulation of human prostate cancer cells.
2008 Aug 28
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
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
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 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
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
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.
Name Type Language
BOLDENONE UNDECYLENATE
GREEN BOOK   USAN  
USAN  
Official Name English
BA-29038
Code English
BOLDENONE UNDECYLENATE [GREEN BOOK]
Common Name English
EQUIPOISE
Brand Name English
ANDROSTA-1,4-DIENE-3-ONE, 17-((1-OXO-10-UNDECENYL)OXY)-, (17.BETA.)-
Systematic Name English
BOLDENONE UNDECYLENATE [USAN]
Common Name English
BOLDENONE UNDECENOATE [MART.]
Common Name English
BOLDENONE 10-UNDECENOATE
MI  
Common Name English
BOLDENONE 10-UNDECENOATE [MI]
Common Name English
17β-Hydroxyandrosta-1,4-dien-3-one 10-undecenoate
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
DEA NO. 4000
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Code System Code Type Description
MERCK INDEX
m2597
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PRIMARY Merck Index
EVMPD
SUB125939
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PRIMARY
DRUG BANK
DB14639
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PRIMARY
CAS
13103-34-9
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ChEMBL
CHEMBL2106059
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WIKIPEDIA
Boldenone undecylenate
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PRIMARY
ECHA (EC/EINECS)
236-024-5
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PRIMARY
EPA CompTox
DTXSID00156854
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SMS_ID
100000151640
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NCI_THESAURUS
C83559
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RXCUI
2289409
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PUBCHEM
11954310
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FDA UNII
ZS6D2ITA30
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PRIMARY
MESH
C001371
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PRIMARY