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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

Molecular Formula C20H28O2
Molecular Weight 300.4351
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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
Metabolism of methandrostenolone in the horse: a gas chromatographic-mass spectrometric investigation of phase I and phase II metabolism.
2001 Dec 5
The hiccup reflex arc and persistent hiccups with high-dose anabolic steroids: is the brainstem the steroid-responsive locus?
2001 Jan-Feb
[Cholestatic jaundice and pruritus].
2002 Sep 18
[Coronary thrombosis and ectasia of coronary arteries after long-term use of anabolic steroids].
2003 Apr
Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats.
2003 Feb
Myocardial infarction with intracoronary thrombus induced by anabolic steroids.
2004 Dec
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
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.
2006 Apr
High amounts of 17-methylated anabolic-androgenic steroids in effervescent tablets on the dietary supplement market.
2007 Feb
[Main symptom jaundice--differential diagnosis at the bedside].
2007 Jan 15
A downscaled multi-residue strategy for detection of anabolic steroids in bovine urine using gas chromatography tandem mass spectrometry (GC-MS3).
2007 Mar 14
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
Humanized animal models to study drug metabolism: no longer a "chimera"?
2009 Oct
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

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:18 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:18 UTC 2023
Record UNII
COZ1R7EOCC
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
METABOLITE -> PARENT
IN-VIVO
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Related Record Type Details
ACTIVE MOIETY