METHANDROSTENOLONE

First approved in 1960

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28O2
Molecular Weight	300.4359
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12C=CC(=O)C=C2CC[C@]3([H])[C@]1([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4(C)O

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:: 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 163 Target ID: CHEMBL3072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9593936	Agonist 2456	Postmenopausal osteoporosis Pituitary-deficient dwarfism
Cytochrome P450 19A1 35 Target ID: CHEMBL3859 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9593936	Activator 1335

Conditions

Condition	Modality	Targets	Highest Phase	Product
Postmenopausal osteoporosis 59 Sources: https://www.healthydietadvisor.com/bodybuilding-supplements/dianabol-review/	Primary	Androgen Receptor	Withdrawn	Dianabol Approved Use It is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism.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1 Sources: https://www.healthydietadvisor.com/bodybuilding-supplements/dianabol-review/	Primary	Androgen Receptor	Withdrawn	Dianabol Approved Use It is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism.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 Health Status: healthy Age Group: 20-48 years Sex: M 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 Health Status: healthy Age Group: 20-48 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/837689

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1470

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP11B1 1 CYP11B2 1

Drug as victim

Target	Modality	Activity
CYP11B1 1	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/22885098/	yes
CYP11B2 1	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/22885098/	yes
CYP3A4 1470	substrate 2752 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
Alfa Chemistry	ACM72639
Aronis	BBC/585
Compound Cloud	6300
Hangzhou APIChem Technology	AC-15917
Hangzhou Yuhao Chemical Technology	YH15865
HongKong Chemhere	SCA04433
IBScreen	BB_NC-00132
IBScreen	STOCK1N-00205
KeyOrganics	VS-09501
Lab Seeker	SC-16233
MolPort	MolPort-002-506-910
MolPort	MolPort-002-508-334
MolPort	MolPort-005-935-516
Molnova	M15782
NCI Plated 2007	42722
NCI Plated 2007	51180
Pharmeks	PHBB_NC-00837
Princeton BioMolecular Research	OSSL_331502
Scientific Exchange	F-446362
ShangHai Biochempartner	BCP10774
Sigma Aldrich	318132
Sigma Aldrich	318132\|ALDRICH
Sigma Aldrich	55609
Sigma Aldrich	55609\|ALDRICH
Sigma Aldrich	90151
Sigma Aldrich	90151\|SIAL
Sigma Aldrich	M-912
Sigma Aldrich	M-912\|CERILLIAN
StruChem	SC-16233
Tetrahedron	TS74635
Toronto Research Chemicals	M226000
Vitas-M Laboratory	BBL029917
Vitas-M Laboratory	STK801870
ZINC	ZINC000003875469	http://zinc15.docking.org/substances/ZINC000003875469
mcule	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
Poststeroid balance disorder--a case report in a body builder.	1999 Aug	10496122
[Microbiological research for the Hungarian pharmaceutical industry].	2001	11769096
Metabolism of methandrostenolone in the horse: a gas chromatographic-mass spectrometric investigation of phase I and phase II metabolism.	2001 Dec 5	11817312
The hiccup reflex arc and persistent hiccups with high-dose anabolic steroids: is the brainstem the steroid-responsive locus?	2001 Jan-Feb	11290884
[Experimental study of pharmacotherapeutic effect of phytoecdisteroids and nerobol in toxic liver damage].	2001 Jul-Aug	11589113
[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
[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
[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
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.	2005 Dec 27	16289956
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
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.	2006 Apr	16488153
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.	2008 Nov 28	19040748
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
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

NSC-42722

Code

English

17.BETA.-HYDROXY-17-METHYLANDROSTA-1,4-DIEN-3-ONE

Systematic Name

English

METANDIENONE [WHO-DD]

Common 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