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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

[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

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

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
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

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
n = 15
Health Status: healthy
Age Group: 20-48 years
Sex: M
Population Size: 15
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Hypoplastic anemia associated with metolazone.
1979 Jul 13
[Hepatoprotective effects of silymarin in androgenic-anabolic steroid-induced liver damage].
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
[Assessment of mutagenic danger of food products].
2004
Myocardial infarction with intracoronary thrombus induced by anabolic steroids.
2004 Dec
[Acute myocardial infarction in a young man who had been using androgenic anabolic steroids].
2004 Jan 22
Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements.
2005 Jan
Steroids' transformations in Penicillium notatum culture.
2005 Mar
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
Childhood virilization and adrenal suppression after ingestion of methandienone and cyproheptadine.
2009 May
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
Chronic anabolic androgenic steroid exposure alters corticotropin releasing factor expression and anxiety-like behaviors in the female mouse.
2010 Nov
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
Metandienone [WHO-DD]
Common Name English
NSC-42722
Code English
17β-Hydroxy-17-methylandrosta-1,4-dien-3-one
Systematic 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 Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
DEA NO. 4000
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
WHO-ATC A14AA03
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
WHO-ATC D11AE01
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
LIVERTOX 613
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
WIKIPEDIA Designer-drugs-Methandrostenolone
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
WHO-VATC QD11AE01
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
Code System Code Type Description
DRUG CENTRAL
1734
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
CAS
72-63-9
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
HSDB
3360
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
ChEMBL
CHEMBL1418176
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
FDA UNII
COZ1R7EOCC
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
WIKIPEDIA
METHANDROSTENOLONE
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
MESH
D008696
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
SMS_ID
100000089098
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
INN
983
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
MERCK INDEX
m7293
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB13586
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
NCI_THESAURUS
C87589
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023276
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
EVMPD
SUB08812MIG
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
PUBCHEM
6300
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
NSC
42722
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY
RXCUI
6818
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-787-2
Created by admin on Fri Dec 15 14:58:19 UTC 2023 , Edited by admin on Fri Dec 15 14:58:19 UTC 2023
PRIMARY