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osteoporosis 59 Sources: https://www.healthydietadvisor.com/bodybuilding-supplements/dianabol-review/	Primary		Withdrawn	Dianabol Approved Use It is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism.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dwarfism 1 Sources: https://www.healthydietadvisor.com/bodybuilding-supplements/dianabol-review/	Primary		Withdrawn	Dianabol Approved Use It is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism.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
Hypoplastic anemia associated with metolazone.	1979 Jul 13	448877
Poststeroid balance disorder--a case report in a body builder.	1999 Aug	10496122
[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
[Acute myocardial infarction in a young man who had been using androgenic anabolic steroids].	2004 Jan 22	14743229
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
Doping control for metandienone using hair analyzed by gas chromatography-tandem mass spectrometry.	2006 May 19	16597518
Anabolic steroid abuse among teenage girls: an illusory problem?	2007 May 11	17127018
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
Steroid metabolism in chimeric mice with humanized liver.	2009 Nov	20355169
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

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