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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

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
PubMed

PubMed

TitleDatePubMed
Microbial transformation of (+)-androsta-1 ,4-diene-3,17-dione by Cephalosporium aphidicola.
2002 Dec
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
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
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
Paracoccidioidomycosis in a woman with idiopathic hirsutism.
2004 Jul
Presence and metabolism of the anabolic steroid boldenone in various animal species: a review.
2004 Jun
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
The progestational and androgenic properties of medroxyprogesterone acetate: gene regulatory overlap with dihydrotestosterone in breast cancer cells.
2005
ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results.
2005 Aug
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
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
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
Formation of boldenone and boldenone-analogues by maggots of Lucilia sericata.
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
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
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
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 Sep
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
Nonlinear immunofluorescent assay for androgenic hormones based on resonant structures.
2008 Aug 18
Nutritional supplements cross-contaminated and faked with doping substances.
2008 Jul
Cytogenetic and clinical studies of a male infant with disorder of sexual development: case report.
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 doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
2008 Sep
Simultaneous measurement of boldenone (alpha and beta), ADD, testosterone, epitestosterone and AED in bovine faeces.
2008 Sep
The risk of hepatotoxicity during long-term and low-dose flutamide treatment in hirsutism.
2009 Mar
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:21:19 GMT 2023
Edited
by admin
on Fri Dec 15 15:21:19 GMT 2023
Record UNII
5H7I2IP58X
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
WIKIPEDIA Designer-drugs-Boldenone
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
DEA NO. 4000
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
Code System Code Type Description
NSC
79102
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
FDA UNII
5H7I2IP58X
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
WIKIPEDIA
BOLDENONE
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
CAS
846-48-0
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
PUBCHEM
13308
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PRIMARY
ChEMBL
CHEMBL2106059
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PRIMARY
DRUG BANK
DB01541
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PRIMARY
INN
2464
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PRIMARY
EVMPD
SUB05869MIG
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PRIMARY
MERCK INDEX
m2597
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID20894201
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PRIMARY
CHEBI
34584
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-686-0
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
MESH
C013915
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
SMS_ID
100000086347
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
NCI_THESAURUS
C75064
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
RXCUI
2289408
Created by admin on Fri Dec 15 15:21:19 GMT 2023 , Edited by admin on Fri Dec 15 15:21:19 GMT 2023
PRIMARY
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