BOLDIONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H24O2
Molecular Weight	284.3927
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23090723 | https://www.ncbi.nlm.nih.gov/pubmed/16308875 | http://www.muscleandsteroids.com/1-4-androstadiene-3b-17b-dione-boldione.html | https://www.ncbi.nlm.nih.gov/pubmed/28710632

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2918514 \| https://www.ncbi.nlm.nih.gov/pubmed/8676338	Inhibitor 8297		120.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Steroid biotransformation by different strains of Micrococcus sp.	2001	11501468
Meta-cleavage enzyme gene tesB is necessary for testosterone degradation in Comamonas testosteroni TA441.	2001 Dec	11739769
Molecular and functional characterization of kshA and kshB, encoding two components of 3-ketosteroid 9alpha-hydroxylase, a class IA monooxygenase, in Rhodococcus erythropolis strain SQ1.	2002 Aug	12180920
[Unexpected formation of an estrone derivative from androsta-1,4-diene-3,17-dione].	2002 Dec	12561240
Isolation of a biodegradable sterol-rich fraction from industrial wastes.	2002 May	11991074
Studies on the catalytic function of aromatase: aromatization of 6-alkoxy-substituted androgens.	2002 Sep	12429140
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	12902225
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	12742113
Mixed culture bioconversion of 16-dehydropregnenolone acetate to androsta-1,4-diene-3,17-dione: optimization of parameters.	2003 Mar-Apr	12675614
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.	2005 Apr 29	15862683
Mycobacterium sp. mutant strain producing 9alpha-hydroxyandrostenedione from sitosterol.	2005 Jun	15647937
Microbial hydroxylation of pregnenolone derivatives.	2005 Nov	16272731
Androstadienetrione, a boldenone-like component, detected in cattle faeces with GC-MS(n) and LC-MS(n).	2005 Sep	16192066
A very efficient bioconversion of soybean phytosterols mixtures to androstanes by mycobacteria.	2006 Aug	16758170
Scanning electron microscopy investigations on bis(2-ethylhexyl)phthalate treated Mycobacterium cells.	2006 Aug	16729266
Neoformation of boldenone and related steroids in faeces of veal calves.	2006 Feb	16449054
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	17386707
The ultimate veal calf reference experiment: hormone residue analysis data obtained by gas and liquid chromatography tandem mass spectrometry.	2007 Mar 14	17386693
Pathology of the testicle and sex accessory glands following the administration of boldenone and boldione as growth promoters in veal calves.	2007 Nov	18057824
Studies directed towards a mechanistic evaluation of inactivation of aromatase by the suicide substrates androsta-1,4-diene-3,17-diones and its 6-ene derivatives aromatase inactivation by the 19-substituted derivatives and their enzymic aromatization.	2007 Nov-Dec	17656084
Development of a rapid normal-phase LC-positive ion APCI-MS method for simultaneous detection and quantitation of cholesterol, androst-4-ene-3,1 7-dione, and androsta-1,4-diene-3,17-dione.	2007 Sep	18019562
Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry.	2008	18085508
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	18615838
Characterization of 3-ketosteroid 9{alpha}-hydroxylase, a Rieske oxygenase in the cholesterol degradation pathway of Mycobacterium tuberculosis.	2009 Apr 10	19234303
Classification of three steroids as schedule III anabolic steroids under the Controlled Substances Act. Final rule.	2009 Dec 4	20169675
A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids.	2009 Jan 15	19064082
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	19409402
Probing the binding pocket of the active site of aromatase with 2-phenylaliphatic androsta-1,4-diene-3,17-dione steroids.	2010 Apr	20096721
Initial steps in anoxic testosterone degradation by Steroidobacter denitrificans.	2010 Jul	20413554
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	20186540
A new steroid-transforming strain of Mycobacterium neoaurum and cloning of 3-ketosteroid 9alpha-hydroxylase in NwIB-01.	2010 Nov	20204712
Quantification of testosterone and metabolites released after alkaline treatment in human urine.	2010 Nov-Dec	21204294
Testosterone metabolism revisited: discovery of new metabolites.	2010 Oct	20711771
Primary hepatocytes as an useful bioassay to characterize metabolism and bioactivity of illicit steroids in cattle.	2012 Oct	22713311

Patents

Sample Use Guides

In Vivo Use Guide

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.

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

Common Name

English

TESTOSTERONE IMPURITY G [EP IMPURITY]

Common Name

English

.DELTA.1,4-ANDROSTADIENE-3,17-DIONE

Common Name

English

(+)-ANDROSTA-1,4-DIENE-3,17-DIONE

Systematic Name

English

EXEMESTANE IMPURITY D [EP IMPURITY]

Common Name

English

Androsta-1,4-diene-3,17-dione

Systematic 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