METHANDROSTENOLONE

First approved in 1960

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28O2
Molecular Weight	300.4351
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XWALNWXLMVGSFR-HLXURNFRSA-N

InChI=1S/C20H28O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h6,9,12,15-17,22H,4-5,7-8,10-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.steroidal.com/steroid-profiles/dianabol/
Curator's Comment: description was created based on several sources, including: Lenehan, P. (2003) "Anabolic steroids", p.101 Retrieved from https://books.google.ru/books?id=TOePv6WpruQC | https://www.healthydietadvisor.com/bodybuilding-supplements/dianabol-review/

Metandienone is an orally active synthetic anabolic-androgenic steroid. In 1970, the FDA accepted that Metandienone (Dianabol) was “Probably Effective” in treating post-menopausal osteoporosis and pituitary-deficient dwarfism. Methandrostenolone is still produced today, but typically in nations with loose prescription drug regulations and by companies that still prefer to cater to an underground athletic market. Androgenic side effects are still common with this substance. This may include bouts of oily skin, acne, and body/facial hair growth. Anabolic/androgenic steroids may also aggravate male pattern hair loss.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167 Target ID: CHEMBL3072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9593936	Agonist 2678
Cytochrome P450 19A1 39 Target ID: CHEMBL3859 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9593936	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Postmenopausal osteoporosis 59 Sources: https://www.healthydietadvisor.com/bodybuilding-supplements/dianabol-review/	Primary		Withdrawn	Dianabol Approved Use It is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism.
Pituitary-deficient dwarfism 1 Sources: https://www.healthydietadvisor.com/bodybuilding-supplements/dianabol-review/	Primary		Withdrawn	Dianabol Approved Use It is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism.

Doses

Dose	Population	Adverse events
15 mg 1 times / day multiple, oral Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/837689	healthy, 20-48 years n = 15 Health Status: healthy Age Group: 20-48 years Sex: M Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/837689	Disc. AE: Infertility... AEs leading to discontinuation/dose reduction: Infertility (15 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/837689

AEs

AE	Significance	Dose	Population
Infertility	15 patients Disc. AE	15 mg 1 times / day multiple, oral Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/837689	healthy, 20-48 years n = 15 Health Status: healthy Age Group: 20-48 years Sex: M Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/837689

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP11B1 1 CYP11B2 1

Drug as victim

Target	Modality	Activity
CYP11B1 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22885098/	yes
CYP11B2 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22885098/	yes
CYP3A4 1737	substrate 3367 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000072639, https://pubmed.ncbi.nlm.nih.gov/10630892/	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-028996	http://www.3bsc.com/index/pro_info.php?id=50253
AHH Chemical co.,ltd	MT-16676	http://www.ahhchemical.com/product/MT-16676.html
Acadechem	ACDS-067615	http://www.acadechemical.com/product/142314
Achemtek	0104-021064	http://www.achemtek.com/72-63-9
Acorn PharmaTech	ACN-031996	http://www.acornpharmatech.com/
Alfa Chemistry	72-63-9	https://www.alfa-chemistry.com/metandienone-cas-72-63-9-item-293466.htm
Aronis	ARONIS24421	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=1561
Aurora Fine Chemicals LLC	K04.045.208	http://online.aurorafinechemicals.com/info?ID=K04.045.208
BioChemPartner	BCP10774	http://www.biochempartner.com/72-63-9-BCP10774
BioCrick	BCC9025	http://www.biocrick.com/Metandienone-BCC9025.html
ChemMol	49425967	http://www.chemmol.com/chemmol/49425967.html
Chemspace	CSSS00000033103	https://chem-space.com/CSSS00000033103
Glentham Life Sciences	GP5474	http://www.glentham.com/products/product/GP5474/
LGC Standards	DRE-C14993000	https://www.lgcstandards.com/US/en/p/DRE-C14993000
LGC Standards	LGCFOR1375.00	https://www.lgcstandards.com/US/en/p/LGCFOR1375.00
MuseChem	R065089	https://www.musechem.com/product/R065089.html
Selleck Chemicals	S4796	http://www.selleckchem.com/products/methandrostenolone.html
Sigma-Aldrich	318132_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/318132?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	55609_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/55609?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	M-912_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/m912?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	90151_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/90151?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S051958	http://www.sinfoobiotech.com/product/1055356
Smolecule	S535091	http://www.smolecule.com/products/s535091
THE BioTek	bt-275120	https://www.thebiotek.com/product/inhibitors/bt-275120
TimTec	SBB080825	http://www.echemstore.com/sbb080825-1s-11s-14s-15s-2r-10r-14-hydroxy-2-14-15-trimethyltetracyclo-8-7-0-0-2-7-0-11-15-heptadeca-3-6-dien-5-one.html
TripleBond	CM0092	http://www.triplebond-canada.com/prod/1441/
abcr GmbH	AB250162	http://www.abcr.de/shop/en/AB250162
mcule	MCULE-1812806265	https://mcule.com/MCULE-1812806265/

PubMed

Title	Date	PubMed
Association of androgenic-anabolic steroid therapy with development of hepatocellular carcinoma.	1972 Dec 16	4117807
Experimental progressive muscular dystrophy and its treatment with high doses anabolizing agents.	1978 Apr	753803
Hypoplastic anemia associated with metolazone.	1979 Jul 13	448877
Bleeding oesophageal varices associated with anabolic steroid use in an athlete.	1990 Oct	2099434
[Comparative study of anabolizing activity of apilac and methandrostenolone on a model of isolated overload of the rat skeletal muscle].	2002 Jan-Feb	12025788
Coronary thrombus in a 23 year old anabolic steroid user.	2002 Oct	12231587
[Cholestatic jaundice and pruritus].	2002 Sep 18	12369223
Practical uses for ecdysteroids in mammals including humans: an update.	2003	15844229
[Hepatoprotective effects of silymarin in androgenic-anabolic steroid-induced liver damage].	2003	15510919
[Coronary thrombosis and ectasia of coronary arteries after long-term use of anabolic steroids].	2003 Apr	12707792
[Severe nephrotic syndrome in a young man taking anabolic steroid and creatine long term].	2003 Dec 7	14725210
Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats.	2003 Feb	12533409
Successful treatment of anabolic steroid-induced azoospermia with human chorionic gonadotropin and human menopausal gonadotropin.	2003 Jun	12801577
Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases.	2003 Sep	12920167
[Assessment of mutagenic danger of food products].	2004	15049156
Myocardial infarction with intracoronary thrombus induced by anabolic steroids.	2004 Dec	15590370
[Acute myocardial infarction in a young man who had been using androgenic anabolic steroids].	2004 Jan 22	14743229
Anabolic-androgenic steroid interaction with rat androgen receptor in vivo and in vitro: a comparative study.	2005 Apr	15876413
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.	2005 Apr 29	15862683
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.	2005 Dec 27	16289956
Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements.	2005 Jan	15808000
Steroids' transformations in Penicillium notatum culture.	2005 Mar	15763598
Dilated cardiomyopathy and acute liver injury associated with combined use of ephedra, gamma-hydroxybutyrate, and anabolic steroids.	2005 May	15899737
Separation and online preconcentration by multistep stacking with large-volume injection of anabolic steroids by capillary electrokinetic chromatography using charged cyclodextrins and UV-absorption detection.	2005 Nov	16318218
Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine.	2006	16804957
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.	2006 Apr	16488153
Research of stimulants and anabolic steroids in dietary supplements.	2006 Feb	16430680
Doping control for metandienone using hair analyzed by gas chromatography-tandem mass spectrometry.	2006 May 19	16597518
High amounts of 17-methylated anabolic-androgenic steroids in effervescent tablets on the dietary supplement market.	2007 Feb	17146762
[Main symptom jaundice--differential diagnosis at the bedside].	2007 Jan 15	17221351
A downscaled multi-residue strategy for detection of anabolic steroids in bovine urine using gas chromatography tandem mass spectrometry (GC-MS3).	2007 Mar 14	17386695
Anabolic steroid abuse among teenage girls: an illusory problem?	2007 May 11	17127018
A league of their own: demographics, motivations and patterns of use of 1,955 male adult non-medical anabolic steroid users in the United States.	2007 Oct 11	17931410
The dire consequences of doping.	2008 Aug 23	18722870
Detection of urinary metabolites common to structurally related 17alpha-alkyl anabolic steroids in horses and application to doping tests in racehorses: methandienone, methandriol, and oxymetholone.	2008 Jun	18544225
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.	2008 Nov 28	19040748
[Conversion of 17 alpha-methyltestosterone to methandrostenolone by the bacterium Pimelobacter simplex VKPM Ac-1632 with the presence of cyclodextrins].	2008 Nov-Dec	19145970
Oxandrolone Improves Height Velocity and BMI in Patients with Cystic Fibrosis.	2009	20145725
A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids.	2009 Jan 15	19064082
Childhood virilization and adrenal suppression after ingestion of methandienone and cyproheptadine.	2009 May	19618666
Combination of liquid-chromatography tandem mass spectrometry in different scan modes with human and chimeric mouse urine for the study of steroid metabolism.	2009 Nov	20355172
Steroid metabolism in chimeric mice with humanized liver.	2009 Nov	20355169
uPA+/+-SCID mouse with humanized liver as a model for in vivo metabolism of exogenous steroids: methandienone as a case study.	2009 Oct	19643840
Humanized animal models to study drug metabolism: no longer a "chimera"?	2009 Oct	19628657
Pulmonary embolism associated with protein C deficiency and abuse of anabolic-androgen steroids.	2010 Apr	18977778
Feasibility of capillary liquid chromatography/microchip atmospheric pressure photoionization mass spectrometry in analyzing anabolic steroids in urine samples.	2010 Apr 15	20209666
CYP21-catalyzed production of the long-term urinary metandienone metabolite 17beta-hydroxymethyl-17 alpha-methyl-18-norandrosta-1,4,13-trien-3-one: a contribution to the fight against doping.	2010 Jan	19919183
Chronic anabolic androgenic steroid exposure alters corticotropin releasing factor expression and anxiety-like behaviors in the female mouse.	2010 Nov	20537804
The anabolic steroid methandienone targets the hypothalamic-pituitary-testicular axis and myostatin signaling in a rat training model.	2012 Jan	21818626
Unexpected contribution of cytochrome P450 enzymes CYP11B2 and CYP21, as well as CYP3A4 in xenobiotic androgen elimination - insights from metandienone metabolism.	2012 Sep 18	22885098

Patents

Sample Use Guides

In Vivo Use Guide

4 mg daily 6 weeks on, 4 weeks off

Route of Administration: Oral

In Vitro Use Guide

Cell death was evaluated by staining PC12 cells treated for 48 h with 75 uM methandienone. Methandienone is toxic to neurons, inducing death in treated cells.

Name

Type

Language

METHANDROSTENOLONE

Common Name

English

metandienone [INN]

Common Name

English

METANDIENONE

Official Name

English

Metandienone [WHO-DD]

Common Name

English

NSC-42722

Code

English

17β-Hydroxy-17-methylandrosta-1,4-dien-3-one

Systematic Name

English

PERBOLIN

Brand Name

English

ANDROSTA-1,4-DIENE-3-ONE, 17-HYDROXY-17-METHYL-, (17.BETA.)-

Common Name

English

METHANDROSTENOLONE [VANDF]

Common Name

English

DIANABOL

Brand Name

English

METHANDROSTENOLONE [HSDB]

Common Name

English

NEROBOL

Brand Name

English

METHANDROSTENOLONE [MI]

Common Name

English

METHANDIENONE [MART.]

Common Name

English

METHANDIENONE

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA14AA03