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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 of METHANDROSTENOLONE

SMILES

C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C

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

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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Dianabol
Primary
Dianabol
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
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
Practical uses for ecdysteroids in mammals including humans: an update.
2003
[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
Successful treatment of anabolic steroid-induced azoospermia with human chorionic gonadotropin and human menopausal gonadotropin.
2003 Jun
Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases.
2003 Sep
[Assessment of mutagenic danger of food products].
2004
[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
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.
2005 Apr 29
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.
2005 Dec 27
Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements.
2005 Jan
Steroids' transformations in Penicillium notatum culture.
2005 Mar
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
Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine.
2006
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.
2006 Apr
Research of stimulants and anabolic steroids in dietary supplements.
2006 Feb
Doping control for metandienone using hair analyzed by gas chromatography-tandem mass spectrometry.
2006 May 19
High amounts of 17-methylated anabolic-androgenic steroids in effervescent tablets on the dietary supplement market.
2007 Feb
Anabolic steroid abuse among teenage girls: an illusory problem?
2007 May 11
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
The dire consequences of doping.
2008 Aug 23
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
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008 Nov 28
[Conversion of 17 alpha-methyltestosterone to methandrostenolone by the bacterium Pimelobacter simplex VKPM Ac-1632 with the presence of cyclodextrins].
2008 Nov-Dec
Oxandrolone Improves Height Velocity and BMI in Patients with Cystic Fibrosis.
2009
A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids.
2009 Jan 15
Childhood virilization and adrenal suppression after ingestion of methandienone and cyproheptadine.
2009 May
Steroid metabolism in chimeric mice with humanized liver.
2009 Nov
Pulmonary embolism associated with protein C deficiency and abuse of anabolic-androgen steroids.
2010 Apr
Feasibility of capillary liquid chromatography/microchip atmospheric pressure photoionization mass spectrometry in analyzing anabolic steroids in urine samples.
2010 Apr 15
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

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
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 Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
DEA NO. 4000
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
WHO-ATC A14AA03
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
WHO-ATC D11AE01
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
LIVERTOX 613
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
NCI_THESAURUS C2360
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
WHO-VATC QD11AE01
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
Code System Code Type Description
CAS
72-63-9
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
HSDB
72-63-9
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
ChEMBL
CHEMBL1418176
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
WIKIPEDIA
METHANDROSTENOLONE
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
MESH
D008696
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
INN
983
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
MERCK INDEX
M7293
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C87589
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
EPA CompTox
72-63-9
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
EVMPD
SUB08812MIG
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
PUBCHEM
6300
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY
RXCUI
6818
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
200-787-2
Created by admin on Tue Oct 22 00:41:39 UTC 2019 , Edited by admin on Tue Oct 22 00:41:39 UTC 2019
PRIMARY