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
Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.
2001 Mar 19
Inhibitors of 5alpha -reductase type I in LNCaP cells from the roots of Angelica koreana.
2002 Feb
An assessment of in vitro androgenic activity and the identification of environmental androgens in United Kingdom estuaries.
2002 Jul
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
Evidence for false-positive results for boldenone testing of veal urine due to faecal cross-contamination during sampling.
2004 Aug
Histopathological effects of boldenone in cattle.
2004 Mar
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
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
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
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
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
Winter profile of plasma sex steroid levels in free-living male western diamond-backed rattlesnakes, Crotalus atrox (Serpentes: Viperidae).
2006 Oct
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
Excretion profile of boldenone and its metabolites after oral administration to veal calves.
2007 Apr 25
Development of an immunosensor for the detection of testosterone in bovine urine.
2007 Jan 30
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
Phytosterols and anabolic agents versus designer drugs.
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
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
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
Validation and application of a yeast bioassay for screening androgenic activity in calf urine and feed.
2009 Apr 1
Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control.
2009 Jan
The risk of hepatotoxicity during long-term and low-dose flutamide treatment in hirsutism.
2009 Mar
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:33:29 UTC 2023
Record UNII
ZS6D2ITA30
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
DEA NO. 4000
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
Code System Code Type Description
MERCK INDEX
m2597
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY Merck Index
EVMPD
SUB125939
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
DRUG BANK
DB14639
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
CAS
13103-34-9
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106059
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
WIKIPEDIA
Boldenone undecylenate
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
ECHA (EC/EINECS)
236-024-5
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID00156854
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
SMS_ID
100000151640
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
NCI_THESAURUS
C83559
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
RXCUI
2289409
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
PUBCHEM
11954310
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
FDA UNII
ZS6D2ITA30
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
MESH
C001371
Created by admin on Fri Dec 15 15:33:29 UTC 2023 , Edited by admin on Fri Dec 15 15:33:29 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY