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

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

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
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
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
Method development for corticosteroids and anabolic steroids by micellar liquid chromatography.
2003 Sep 5
Histopathological effects of boldenone in cattle.
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
ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results.
2005 Aug
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
Endogenous occurrence of some anabolic steroids in swine matrices.
2005 Sep
Androstadienetrione, a boldenone-like component, detected in cattle faeces with GC-MS(n) and LC-MS(n).
2005 Sep
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
Excretion profile of boldenone and its metabolites after oral administration to veal calves.
2007 Apr 25
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
Excretion profile of boldenone in urine of veal calves fed two different milk replacers.
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
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
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
Mitochondrial redox signaling by p66Shc is involved in regulating androgenic growth stimulation of human prostate cancer cells.
2008 Aug 28
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
[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
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
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
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
INN   MI  
INN  
Official Name English
NSC-79102
Code English
boldenone [INN]
Common Name English
TESTOSTERONE IMPURITY H [EP IMPURITY]
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
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WIKIPEDIA Designer-drugs-Boldenone
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NCI_THESAURUS C2360
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DEA NO. 4000
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Code System Code Type Description
NSC
79102
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FDA UNII
5H7I2IP58X
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WIKIPEDIA
BOLDENONE
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CAS
846-48-0
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PUBCHEM
13308
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ChEMBL
CHEMBL2106059
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DRUG BANK
DB01541
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INN
2464
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EVMPD
SUB05869MIG
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MERCK INDEX
m2597
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PRIMARY Merck Index
EPA CompTox
DTXSID20894201
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CHEBI
34584
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ECHA (EC/EINECS)
212-686-0
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MESH
C013915
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SMS_ID
100000086347
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NCI_THESAURUS
C75064
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RXCUI
2289408
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