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
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
Role of androgens in the growth of endometrial carcinoma: an in vivo animal model.
2001 Feb
Novel amino acid substitutional mutation, tyrosine-739-aspartic acid, in the androgen receptor gene in complete androgen insensitivity syndrome.
2001 Jun
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
Inhibitors of 5alpha -reductase type I in LNCaP cells from the roots of Angelica koreana.
2002 Feb
Transformations of testosterone and related steroids in Absidia glauca culture.
2003
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
Presence and metabolism of the anabolic steroid boldenone in various animal species: a review.
2004 Jun
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
Very short term dehydroepiandrosterone treatment in female adrenal failure: impact on carbohydrate, lipid and protein metabolism.
2005 Jan
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.
2005 May
Neoformation of boldenone and related steroids in faeces of veal calves.
2006 Feb
Dehydroepiandrosterone decreases while cortisol increases in vitro growth and viability of Entamoeba histolytica.
2006 Feb
Effects of chronic exposure to sodium arsenite on hypothalamo-pituitary-testicular activities in adult rats: possible an estrogenic mode of action.
2006 Feb 16
[Rhabdomyolysis in a bodybuilder using steroids].
2006 May 13
Screening of boldenone and methylboldenone in bovine urine using disposable electrochemical immunosensors.
2006 Sep
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
Androgen receptor or estrogen receptor-beta blockade alters DHEA-, DHT-, and E(2)-induced proliferation and PSA production in human prostate cancer cells.
2007 Aug 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
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
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
In vitro and in vivo effects of bicalutamide on the expression of TrkA and P75 neurotrophin receptors in prostate carcinoma.
2007 Sep 1
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
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
Validation and application of a yeast bioassay for screening androgenic activity in calf urine and feed.
2009 Apr 1
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 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
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
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