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
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C
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 |
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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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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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Coronary thrombus in a 23 year old anabolic steroid user. | 2002 Oct |
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Practical uses for ecdysteroids in mammals including humans: an update. | 2003 |
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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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Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry. | 2005 Apr 29 |
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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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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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Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry. | 2006 Apr |
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Research of stimulants and anabolic steroids in dietary supplements. | 2006 Feb |
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Doping control for metandienone using hair analyzed by gas chromatography-tandem mass spectrometry. | 2006 May 19 |
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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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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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[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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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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Chronic anabolic androgenic steroid exposure alters corticotropin releasing factor expression and anxiety-like behaviors in the female mouse. | 2010 Nov |
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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WIKIPEDIA |
Designer-drugs-Methandrostenolone
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NCI_THESAURUS |
C2360
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WHO-VATC |
QD11AE01
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1734
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72-63-9
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3360
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CHEMBL1418176
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COZ1R7EOCC
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METHANDROSTENOLONE
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D008696
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100000089098
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983
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M7293
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DB13586
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C87589
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DTXSID2023276
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SUB08812MIG
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6300
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42722
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6818
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200-787-2
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ACTIVE MOIETY
METABOLITE (PARENT)