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

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
Regulation of the epididymal glutathione peroxidase-like protein in the mouse: dependence upon androgens and testicular factors.
1992 Nov
Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.
2001 Mar 19
DHT levels.
2002 Apr
The popliteal-artery entrapment syndrome in a patient using anabolic steroids.
2002 Apr 18
Androgen replacement therapy and prostate safety.
2002 Feb
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
Direct detection of boldenone sulfate and glucuronide conjugates in horse urine by ion trap liquid chromatography-mass spectrometry.
2004 Dec 25
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
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.
2005 Dec 27
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
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
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
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
[Rhabdomyolysis in a bodybuilder using steroids].
2006 May 13
Screening of boldenone and methylboldenone in bovine urine using disposable electrochemical immunosensors.
2006 Sep
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
Rapid screening of doping agents in human urine by vacuum MALDI-linear ion trap mass spectrometry.
2007 Aug 1
Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted.
2007 Jul
Pathology of the testicle and sex accessory glands following the administration of boldenone and boldione as growth promoters in veal calves.
2007 Nov
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
Mitochondrial redox signaling by p66Shc is involved in regulating androgenic growth stimulation of human prostate cancer cells.
2008 Aug 28
[Determination of eleven steroid hormones in animal muscle tissues and eggs using ultra-performance liquid chromatography-tandem mass spectrometry].
2008 Nov
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
2008 Sep
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
Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control.
2009 Jan
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
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
ChEMBL
CHEMBL2106059
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
DRUG BANK
DB01541
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
INN
2464
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
EVMPD
SUB05869MIG
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
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
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
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
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY