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
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
DescriptionSources: 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/
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 |
---|---|---|---|
Target ID: CHEMBL3072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9593936 |
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Target ID: CHEMBL3859 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9593936 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Dianabol Approved UseIt is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism. |
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Primary | Dianabol Approved UseIt is indicated for the treatment of post-menopausal osteoporosis and pituitary-deficient dwarfism. |
Doses
Dose | Population | Adverse events |
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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 n = 15 Health Status: healthy Age Group: 20-48 years Sex: M Population Size: 15 Sources: |
Disc. AE: Infertility... AEs leading to discontinuation/dose reduction: Infertility (15 patients) Sources: |
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: |
healthy, 20-48 years n = 15 Health Status: healthy Age Group: 20-48 years Sex: M Population Size: 15 Sources: |
PubMed
Title | Date | PubMed |
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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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Metabolism of methandrostenolone in the horse: a gas chromatographic-mass spectrometric investigation of phase I and phase II metabolism. | 2001 Dec 5 |
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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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[Hepatoprotective effects of silymarin in androgenic-anabolic steroid-induced liver damage]. | 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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Myocardial infarction with intracoronary thrombus induced by anabolic steroids. | 2004 Dec |
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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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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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Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry. | 2006 Apr |
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High amounts of 17-methylated anabolic-androgenic steroids in effervescent tablets on the dietary supplement market. | 2007 Feb |
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[Main symptom jaundice--differential diagnosis at the bedside]. | 2007 Jan 15 |
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A downscaled multi-residue strategy for detection of anabolic steroids in bovine urine using gas chromatography tandem mass spectrometry (GC-MS3). | 2007 Mar 14 |
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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 |
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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 |
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The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports. | 2008 Nov 28 |
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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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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 |
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Steroid metabolism in chimeric mice with humanized liver. | 2009 Nov |
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uPA+/+-SCID mouse with humanized liver as a model for in vivo metabolism of exogenous steroids: methandienone as a case study. | 2009 Oct |
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Humanized animal models to study drug metabolism: no longer a "chimera"? | 2009 Oct |
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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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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 |
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Chronic anabolic androgenic steroid exposure alters corticotropin releasing factor expression and anxiety-like behaviors in the female mouse. | 2010 Nov |
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The anabolic steroid methandienone targets the hypothalamic-pituitary-testicular axis and myostatin signaling in a rat training model. | 2012 Jan |
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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
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23675320
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.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QA14AA03
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DEA NO. |
4000
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WHO-ATC |
A14AA03
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WHO-ATC |
D11AE01
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LIVERTOX |
613
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NCI_THESAURUS |
C2360
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WHO-VATC |
QD11AE01
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Code System | Code | Type | Description | ||
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1734
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PRIMARY | |||
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72-63-9
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PRIMARY | |||
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3360
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PRIMARY | |||
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CHEMBL1418176
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COZ1R7EOCC
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METHANDROSTENOLONE
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D008696
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983
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PRIMARY | |||
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M7293
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PRIMARY | Merck Index | ||
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DB13586
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PRIMARY | |||
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C87589
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PRIMARY | |||
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72-63-9
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SUB08812MIG
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6300
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6818
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PRIMARY | RxNorm | ||
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200-787-2
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)