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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H24O2
Molecular Weight 284.3934
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BOLDIONE

SMILES

C[C@@]12C=CC(=O)C=C2CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@@]31[H]

InChI

InChIKey=LUJVUUWNAPIQQI-QAGGRKNESA-N
InChI=1S/C19H24O2/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/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H24O2
Molecular Weight 284.3934
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Boldione, also known as androstadienedione or 1-dehydroandrostenedione, as well as 1,4-androstadiene-3,17-dione, is an important industrial precursor for various steroid hormones. Boldione is a direct precursor (prohormone) to the anabolic steroid boldenone (1,4-androstadiene-17beta-ol-3-one). It is advertised as a highly anabolic/androgenic compound promoting muscularity, enhancing strength and overall physical performance, and is available on the Internet and in health stores. Boldione was marketed as a prohormone “dietary supplement” for many years in the mid-2000’s, but it is truly a potent precursor (ie. converts in the body) to the anabolic steroid Boldenone. In 2005 the Anabolic Steroid Control Act of 2005 classified boldenone as a Schedule III controlled illegal steroid.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
120.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Biotransformation of (+)-androst-4-ene-3,17-dione.
2004 Dec
Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements.
2004 Jul
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
The effect of ethambutol on mycobacterial cell wall permeability to hydrophobic compounds.
2005
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.
2005 Apr 29
ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results.
2005 Aug
Mycobacterium sp. mutant strain producing 9alpha-hydroxyandrostenedione from sitosterol.
2005 Jun
Bioconversion of phytosterols to androstanes by mycobacteria growing on sugar cane mud.
2005 Mar
Persistence of testosterone and 17beta-estradiol in soils receiving swine manure or municipal biosolids.
2005 May-Jun
Persistence and pathways of testosterone dissipation in agricultural soil.
2005 May-Jun
Microbial hydroxylation of pregnenolone derivatives.
2005 Nov
Androstadienetrione, a boldenone-like component, detected in cattle faeces with GC-MS(n) and LC-MS(n).
2005 Sep
Characterization of boldione and its metabolites in human urine by liquid chromatography/electrospray ionization mass spectrometry and gas chromatography/mass spectrometry.
2006
Scanning electron microscopy investigations on bis(2-ethylhexyl)phthalate treated Mycobacterium cells.
2006 Aug
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
Effect of anabolics on bovine granulosa-luteal cell primary cultures.
2007
Excretion profile of boldenone and its metabolites after oral administration to veal calves.
2007 Apr 25
An in vitro study on metabolism of 17beta-boldenone and boldione using cattle liver and kidney subcellular fractions.
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
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
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
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
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
Naturally occurring progesterone in loblolly pine (Pinus taeda L.): a major steroid precursor of environmental androgens.
2008 Jun
Characterization of 3-ketosteroid 9{alpha}-hydroxylase, a Rieske oxygenase in the cholesterol degradation pathway of Mycobacterium tuberculosis.
2009 Apr 10
Cholesterol oxidase: physiological functions.
2009 Dec
Simultaneous determination of 15 steroids in rat blood via gas chromatography-mass spectrometry to evaluate the impact of emasculation on adrenal.
2009 Dec 15
Classification of three steroids as schedule III anabolic steroids under the Controlled Substances Act. Final rule.
2009 Dec 4
A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids.
2009 Jan 15
Excretion of endogenous boldione in human urine: influence of phytosterol consumption.
2009 Oct
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
Aromatase inactivation by 2-substituted derivatives of the suicide substrate androsta-1,4-diene-3,17-dione.
2009 Sep
Sitosterol bioconversion with resting cells in liquid polymer based systems.
2009 Sep
Investigation on possible transformations of cortisol, cortisone and cortisol glucuronide in bovine faecal matter using liquid chromatography-mass spectrometry.
2010 Apr
Probing the binding pocket of the active site of aromatase with 2-phenylaliphatic androsta-1,4-diene-3,17-dione steroids.
2010 Apr
Initial steps in anoxic testosterone degradation by Steroidobacter denitrificans.
2010 Jul
Degradation kinetics of testosterone by manure-borne bacteria: influence of temperature, pH, glucose amendments, and dissolved oxygen.
2010 Jul-Aug
Characterisation of steroids in wooden crates of veal calves by accelerated solvent extraction (ASE) and ultra-high performance liquid chromatography coupled to triple quadrupole mass spectrometry (U-HPLC-QqQ-MS-MS).
2010 May
Cholesterol utilization in mycobacteria is controlled by two TetR-type transcriptional regulators: kstR and kstR2.
2010 May
Cholesterol biotransformation to androsta-1,4-diene-3,17-dione by growing cells of Chryseobacterium gleum.
2010 May
A new steroid-transforming strain of Mycobacterium neoaurum and cloning of 3-ketosteroid 9alpha-hydroxylase in NwIB-01.
2010 Nov
Quantification of testosterone and metabolites released after alkaline treatment in human urine.
2010 Nov-Dec
Testosterone metabolism revisited: discovery of new metabolites.
2010 Oct
Primary hepatocytes as an useful bioassay to characterize metabolism and bioactivity of illicit steroids in cattle.
2012 Oct
Patents

Sample Use Guides

2-4 pills (400-800mg) a day.
Route of Administration: Oral
In Vitro Use Guide
Boldione inhibited Cytochrome P450 19A1 in human placental microsomes with the IC50 value of 530 nM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:37:22 UTC 2021
Edited
by admin
on Sat Jun 26 08:37:22 UTC 2021
Record UNII
2166Q8568W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BOLDIONE
Common Name English
ANDROSTADIENEDIONE
Systematic Name English
1-DEHYDROANDROSTENEDIONE
Common Name English
ANDROSTA-1,4-DIEN-3,17-DIONE
Systematic Name English
EXEMESTANE RELATED COMPOUND C CIII
USP-RS  
Common Name English
.DELTA.1,4-ANDROSTADIENE-3,17-DIONE
Common Name English
(+)-ANDROSTA-1,4-DIENE-3,17-DIONE
Systematic Name English
TESTOSTERONE IMPURITY G [EP]
Common Name English
J38.935H
Code English
1,4-ANDROSTADIENE-3,17-DIONE
Systematic Name English
NSC-49080
Code English
ANDROSTANE-1,4-DIENE-3,17-DIONE
Systematic Name English
EXEMESTANE RELATED COMPOUND C [USP-RS]
Common Name English
Classification Tree Code System Code
DEA NO. 4000
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
212-977-2
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY
EVMPD
SUB194899
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY
WIKIPEDIA
BOLDIONE
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY
USP_CATALOG
1269083
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY USP-RS
PUBCHEM
13472
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY
MESH
C006573
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY
FDA UNII
2166Q8568W
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY
CAS
897-06-3
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY
DRUG BANK
DB07373
Created by admin on Sat Jun 26 08:37:22 UTC 2021 , Edited by admin on Sat Jun 26 08:37:22 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP