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

Molecular Formula C30H44O3
Molecular Weight 452.6686
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
Regulation of the epididymal glutathione peroxidase-like protein in the mouse: dependence upon androgens and testicular factors.
1992 Nov
DHT levels.
2002 Apr
Microbial transformation of (+)-androsta-1 ,4-diene-3,17-dione by Cephalosporium aphidicola.
2002 Dec
Androgen replacement therapy and prostate safety.
2002 Feb
An assessment of in vitro androgenic activity and the identification of environmental androgens in United Kingdom estuaries.
2002 Jul
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
Confirmatory analysis of 17beta-boldenone, 17alpha-boldenone and androsta-1,4-diene-3,17-dione in bovine urine by liquid chromatography-tandem mass spectrometry.
2003 Jun 15
Dihydrotestesterone induction of EPHB2 expression in the female genital tubercle mimics male pattern of expression during embryogenesis.
2003 Oct
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
Method development for corticosteroids and anabolic steroids by micellar liquid chromatography.
2003 Sep 5
Evidence for false-positive results for boldenone testing of veal urine due to faecal cross-contamination during sampling.
2004 Aug
Comparison of two in vivo models for prostate cancer: orthotopic and intratesticular inoculation of LNCaP or PC-3 cells.
2004 Dec
Biotransformation of (+)-androst-4-ene-3,17-dione.
2004 Dec
Direct detection of boldenone sulfate and glucuronide conjugates in horse urine by ion trap liquid chromatography-mass spectrometry.
2004 Dec 25
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
Very short term dehydroepiandrosterone treatment in female adrenal failure: impact on carbohydrate, lipid and protein metabolism.
2005 Jan
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
Androstadienetrione, a boldenone-like component, detected in cattle faeces with GC-MS(n) and LC-MS(n).
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
Characterization of boldione and its metabolites in human urine by liquid chromatography/electrospray ionization mass spectrometry and gas chromatography/mass spectrometry.
2006
DU-145 and PC-3 human prostate cancer cell lines express androgen receptor: implications for the androgen receptor functions and regulation.
2006 Apr 17
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
Alteration of gene expression in response to bone morphogenetic protein-2 in androgen-dependent human prostate cancer LNCaP cells.
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
Analysis of anabolic steroids in hair by GC/MS/MS.
2007 Apr
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
Development of a method which discriminates between endogenous and exogenous beta-boldenone.
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
Nonlinear immunofluorescent assay for androgenic hormones based on resonant structures.
2008 Aug 18
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
Cytogenetic and clinical studies of a male infant with disorder of sexual development: case report.
2008 Nov
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
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
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 Fri Dec 15 15:33:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:33:29 GMT 2023
Record UNII
ZS6D2ITA30
Record Status Validated (UNII)
Record Version
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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
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
Code System Code Type Description
MERCK INDEX
m2597
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY Merck Index
EVMPD
SUB125939
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PRIMARY
DRUG BANK
DB14639
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
CAS
13103-34-9
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106059
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
WIKIPEDIA
Boldenone undecylenate
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
ECHA (EC/EINECS)
236-024-5
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID00156854
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
SMS_ID
100000151640
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
NCI_THESAURUS
C83559
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
RXCUI
2289409
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
PUBCHEM
11954310
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
FDA UNII
ZS6D2ITA30
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
MESH
C001371
Created by admin on Fri Dec 15 15:33:29 GMT 2023 , Edited by admin on Fri Dec 15 15:33:29 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY