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
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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Association of androgenic-anabolic steroid therapy with development of hepatocellular carcinoma. | 1972 Dec 16 |
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| Experimental progressive muscular dystrophy and its treatment with high doses anabolizing agents. | 1978 Apr |
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| Hypoplastic anemia associated with metolazone. | 1979 Jul 13 |
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| Bleeding oesophageal varices associated with anabolic steroid use in an athlete. | 1990 Oct |
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| Poststeroid balance disorder--a case report in a body builder. | 1999 Aug |
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| [Microbiological research for the Hungarian pharmaceutical industry]. | 2001 |
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| The hiccup reflex arc and persistent hiccups with high-dose anabolic steroids: is the brainstem the steroid-responsive locus? | 2001 Jan-Feb |
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| [Experimental study of pharmacotherapeutic effect of phytoecdisteroids and nerobol in toxic liver damage]. | 2001 Jul-Aug |
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| [Comparative study of anabolizing activity of apilac and methandrostenolone on a model of isolated overload of the rat skeletal muscle]. | 2002 Jan-Feb |
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| Coronary thrombus in a 23 year old anabolic steroid user. | 2002 Oct |
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| [Cholestatic jaundice and pruritus]. | 2002 Sep 18 |
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| Practical uses for ecdysteroids in mammals including humans: an update. | 2003 |
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| [Coronary thrombosis and ectasia of coronary arteries after long-term use of anabolic steroids]. | 2003 Apr |
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| [Severe nephrotic syndrome in a young man taking anabolic steroid and creatine long term]. | 2003 Dec 7 |
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| Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats. | 2003 Feb |
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| Successful treatment of anabolic steroid-induced azoospermia with human chorionic gonadotropin and human menopausal gonadotropin. | 2003 Jun |
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| Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases. | 2003 Sep |
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| [Assessment of mutagenic danger of food products]. | 2004 |
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| [Acute myocardial infarction in a young man who had been using androgenic anabolic steroids]. | 2004 Jan 22 |
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| Anabolic-androgenic steroid interaction with rat androgen receptor in vivo and in vitro: a comparative study. | 2005 Apr |
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| Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry. | 2005 Apr 29 |
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| Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry. | 2005 Dec 27 |
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| Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements. | 2005 Jan |
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| Steroids' transformations in Penicillium notatum culture. | 2005 Mar |
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| Dilated cardiomyopathy and acute liver injury associated with combined use of ephedra, gamma-hydroxybutyrate, and anabolic steroids. | 2005 May |
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| 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 |
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| 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 |
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| Anabolic steroid abuse among teenage girls: an illusory problem? | 2007 May 11 |
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| 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 |
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| 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 |
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| [Conversion of 17 alpha-methyltestosterone to methandrostenolone by the bacterium Pimelobacter simplex VKPM Ac-1632 with the presence of cyclodextrins]. | 2008 Nov-Dec |
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| Oxandrolone Improves Height Velocity and BMI in Patients with Cystic Fibrosis. | 2009 |
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| A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids. | 2009 Jan 15 |
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| Childhood virilization and adrenal suppression after ingestion of methandienone and cyproheptadine. | 2009 May |
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| Steroid metabolism in chimeric mice with humanized liver. | 2009 Nov |
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| Pulmonary embolism associated with protein C deficiency and abuse of anabolic-androgen steroids. | 2010 Apr |
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| Feasibility of capillary liquid chromatography/microchip atmospheric pressure photoionization mass spectrometry in analyzing anabolic steroids in urine samples. | 2010 Apr 15 |
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| 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
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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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
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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
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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
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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
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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
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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
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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 | ||
|---|---|---|---|---|---|
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | Merck Index | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | RxNorm | ||
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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
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
