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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
Novel amino acid substitutional mutation, tyrosine-739-aspartic acid, in the androgen receptor gene in complete androgen insensitivity syndrome.
2001 Jun
Interactions of androgens, green tea catechins and the antiandrogen flutamide with the external glucose-binding site of the human erythrocyte glucose transporter GLUT1.
2003 Oct
Direct detection of boldenone sulfate and glucuronide conjugates in horse urine by ion trap liquid chromatography-mass spectrometry.
2004 Dec 25
Presence and metabolism of the anabolic steroid boldenone in various animal species: a review.
2004 Jun
Histopathological effects of boldenone in cattle.
2004 Mar
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
Steroids' transformations in Penicillium notatum culture.
2005 Mar
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.
2005 May
A prospective analysis of the time to normalization of serum androgens following 6 months of androgen deprivation therapy in patients on a randomized phase III clinical trial using limited hormonal therapy.
2005 May
Endogenous occurrence of some anabolic steroids in swine matrices.
2005 Sep
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
Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids.
2006
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.
2006 Apr
DU-145 and PC-3 human prostate cancer cell lines express androgen receptor: implications for the androgen receptor functions and regulation.
2006 Apr 17
17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties.
2006 Aug 20
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
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
Multi residue screening of intact testosterone esters and boldenone undecylenate in bovine hair using liquid chromatography electrospray tandem mass spectrometry.
2006 Jan 2
Winter profile of plasma sex steroid levels in free-living male western diamond-backed rattlesnakes, Crotalus atrox (Serpentes: Viperidae).
2006 Oct
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
Effects of steroidal and non-steroidal antiandrogens on wild-type and mutant androgen receptors.
2007 Jun 1
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
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
Nonlinear immunofluorescent assay for androgenic hormones based on resonant structures.
2008 Aug 18
Acupuncture and exercise restore adipose tissue expression of sympathetic markers and improve ovarian morphology in rats with dihydrotestosterone-induced PCOS.
2009 Apr
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
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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CAS
13103-34-9
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ChEMBL
CHEMBL2106059
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WIKIPEDIA
Boldenone undecylenate
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ECHA (EC/EINECS)
236-024-5
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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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MESH
C001371
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