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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 of METHANDROSTENOLONE

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
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Dianabol

Approved Use

It is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism.
Primary
Dianabol

Approved Use

It is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism.
Doses

Doses

DosePopulationAdverse 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:
healthy, 20-48 years
Health Status: healthy
Age Group: 20-48 years
Sex: M
Sources:
Disc. AE: Infertility...
AEs leading to
discontinuation/dose reduction:
Infertility (15 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
healthy, 20-48 years
Health Status: healthy
Age Group: 20-48 years
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim
PubMed

PubMed

TitleDatePubMed
Association of androgenic-anabolic steroid therapy with development of hepatocellular carcinoma.
1972 Dec 16
Experimental progressive muscular dystrophy and its treatment with high doses anabolizing agents.
1978 Apr
Hypoplastic anemia associated with metolazone.
1979 Jul 13
Bleeding oesophageal varices associated with anabolic steroid use in an athlete.
1990 Oct
Poststeroid balance disorder--a case report in a body builder.
1999 Aug
[Microbiological research for the Hungarian pharmaceutical industry].
2001
Metabolism of methandrostenolone in the horse: a gas chromatographic-mass spectrometric investigation of phase I and phase II metabolism.
2001 Dec 5
The hiccup reflex arc and persistent hiccups with high-dose anabolic steroids: is the brainstem the steroid-responsive locus?
2001 Jan-Feb
[Experimental study of pharmacotherapeutic effect of phytoecdisteroids and nerobol in toxic liver damage].
2001 Jul-Aug
[Comparative study of anabolizing activity of apilac and methandrostenolone on a model of isolated overload of the rat skeletal muscle].
2002 Jan-Feb
Coronary thrombus in a 23 year old anabolic steroid user.
2002 Oct
[Cholestatic jaundice and pruritus].
2002 Sep 18
[Coronary thrombosis and ectasia of coronary arteries after long-term use of anabolic steroids].
2003 Apr
[Severe nephrotic syndrome in a young man taking anabolic steroid and creatine long term].
2003 Dec 7
Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats.
2003 Feb
[Acute myocardial infarction in a young man who had been using androgenic anabolic steroids].
2004 Jan 22
Anabolic-androgenic steroid interaction with rat androgen receptor in vivo and in vitro: a comparative study.
2005 Apr
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.
2005 Dec 27
Dilated cardiomyopathy and acute liver injury associated with combined use of ephedra, gamma-hydroxybutyrate, and anabolic steroids.
2005 May
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
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.
2006 Apr
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008 Nov 28
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
Steroid metabolism in chimeric mice with humanized liver.
2009 Nov
uPA+/+-SCID mouse with humanized liver as a model for in vivo metabolism of exogenous steroids: methandienone as a case study.
2009 Oct
Chronic anabolic androgenic steroid exposure alters corticotropin releasing factor expression and anxiety-like behaviors in the female mouse.
2010 Nov
The anabolic steroid methandienone targets the hypothalamic-pituitary-testicular axis and myostatin signaling in a rat training model.
2012 Jan
Unexpected contribution of cytochrome P450 enzymes CYP11B2 and CYP21, as well as CYP3A4 in xenobiotic androgen elimination - insights from metandienone metabolism.
2012 Sep 18
Patents

Patents

Sample Use Guides

4 mg daily 6 weeks on, 4 weeks off
Route of Administration: Oral
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
HSDB   MI   VANDF  
Common Name English
METANDIENONE [INN]
Common Name English
METANDIENONE
INN   WHO-DD  
INN  
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
MART.  
Common Name English
Classification Tree Code System Code
WHO-VATC QA14AA03
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
DEA NO. 4000
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
WHO-ATC A14AA03
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
WHO-ATC D11AE01
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
LIVERTOX 613
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
NCI_THESAURUS C2360
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
WHO-VATC QD11AE01
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1734
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
CAS
72-63-9
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
HSDB
3360
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL1418176
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
FDA UNII
COZ1R7EOCC
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
WIKIPEDIA
METHANDROSTENOLONE
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
MESH
D008696
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
INN
983
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
MERCK INDEX
M7293
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB13586
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
NCI_THESAURUS
C87589
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
EPA CompTox
72-63-9
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
EVMPD
SUB08812MIG
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
PUBCHEM
6300
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY
RXCUI
6818
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
200-787-2
Created by admin on Fri Jun 25 23:51:49 UTC 2021 , Edited by admin on Fri Jun 25 23:51:49 UTC 2021
PRIMARY