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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H32O2
Molecular Weight 304.4669
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MESTANOLONE

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC(=O)CC[C@]34C

InChI

InChIKey=WYZDXEKUWRCKOB-YDSAWKJFSA-N
InChI=1S/C20H32O2/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/h13,15-17,22H,4-12H2,1-3H3/t13-,15+,16-,17-,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.steroid.com/Ermalone.php

Mestanolone is an oral analogue of dihydrotestosterone. This steroid is a 17-alpha methylated form of this potent endogenous androgen, being essentially (in structure) to dihydrotestosterone what methyltestosterone is to testosterone. Overall, mestanolone has an activity profile not very dissimilar from the hormone it is derived from. Like dihydrotestosterone, mestanolone is primarily androgenic in nature, displaying a low level of anabolic activity. Both dihydrotestosterone and mestanolone are also devoid of estrogenic activity. Dihydrotestosterone was synthesized in 1935. After that 17-alpha-methylated version also appeared. This steroid was not frequently used in clinical medicine. It was produced under the name of ermalon for short period of time. Most studies involving mestanolone were carried out in the 1950s and 1960s. In the 1970s and 1980s it was used as part of the East German doping machine. Mestanolone was evaluated not for its anabolic ability but for its androgenic essence. It improved the functioning of the CNS and neuromuscular interaction. Athletes claimed that it did not make them huge, but gave them speed, strength, aggression, stamina and resistance to stress. Mestanolone is still valued as an oral androgen.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Histopathology as a tool for the evaluation of endocrine disruption in zebrafish (Danio rerio).
2003 Apr
Efficient oxidizing methods for the synthesis of oxandrolone intermediates.
2004 Aug
Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites.
2005 Aug
Luteinizing hormone, follicle stimulating hormone, and gonadotropin releasing hormone mRNA expression of Xenopus laevis in response to endocrine disrupting compounds affecting reproductive biology.
2006 Apr
Sex reversal in medaka treated in vitro with 17alpha-methyldihydrotestosterone during oocyte maturation.
2006 Jan
Testosterone content of developing eggs and sex reversal in the medaka (Oryzias latipes).
2006 Jan 1
Endocrine disrupters with (anti)estrogenic and (anti)androgenic modes of action affecting reproductive biology of Xenopus laevis: I. Effects on sex steroid levels and biomarker expression.
2007 Jan
Gonadal differentiation and hormonal sex reversal in Arctic charr (Salvelinus alpinus).
2007 Sep 1
Identification and quantification of metabolites common to 17alpha-methyltestosterone and mestanolone in horse urine.
2007 Sep 21
Hepatic gene expression profiling using GeneChips in zebrafish exposed to 17alpha-methyldihydrotestosterone.
2008 Apr 28
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
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
2008 Sep
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

Sample Use Guides

Dosages range from 10 mg to 30 mg a day for males for 6-8 weeks
Route of Administration: Oral
Intrafollicular oocytes of the medaka Oryzias latipes were incubated for about 10 h in the absence or the presence of Mestanolone at 1–100 ng/mL.
Name Type Language
MESTANOLONE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
METHYBOL
Brand Name English
17.ALPHA.-METHYLANDROSTAN-3-ON-17.BETA.-OL
Common Name English
MESTANOLONE [MI]
Common Name English
17.ALPHA.-METHYLANDROSTAN-17.BETA.-OL-3-ONE
Common Name English
MESTANOLONE [JAN]
Common Name English
Mestanolone [WHO-DD]
Common Name English
NSC-18219
Code English
MESANOLON
Brand Name English
17.BETA.-HYDROXY-17-METHYL-5.ALPHA.-ANDROSTAN-3-ONE
Systematic Name English
ASSIMIL
Brand Name English
mestanolone [INN]
Common Name English
(5.ALPHA.,17.BETA.)-17-HYDROXY-17-METHYLANDROSTAN-3-ONE
Systematic Name English
STANOZOLOL IMPURITY A [EP IMPURITY]
Common Name English
TANTARONE
Brand Name English
17.BETA.-HYDROXY-17.ALPHA.-METHYL-3-ANDROSTANONE
Systematic Name English
ERMALONE
Brand Name English
MESTANOLONE [MART.]
Common Name English
Classification Tree Code System Code
DEA NO. 4000
Created by admin on Fri Dec 15 17:40:07 GMT 2023 , Edited by admin on Fri Dec 15 17:40:07 GMT 2023
WIKIPEDIA Designer-drugs-Mestanolone
Created by admin on Fri Dec 15 17:40:07 GMT 2023 , Edited by admin on Fri Dec 15 17:40:07 GMT 2023
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 17:40:07 GMT 2023 , Edited by admin on Fri Dec 15 17:40:07 GMT 2023
Code System Code Type Description
FDA UNII
S712YZ168E
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PRIMARY
CAS
521-11-9
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ECHA (EC/EINECS)
208-302-6
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MERCK INDEX
m7255
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PRIMARY Merck Index
MESH
C008376
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ChEMBL
CHEMBL261514
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DRUG CENTRAL
3341
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EPA CompTox
DTXSID0048973
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PRIMARY
PUBCHEM
10633
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NCI_THESAURUS
C83939
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NSC
18219
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PRIMARY
INN
862
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PRIMARY
EVMPD
SUB08789MIG
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PRIMARY
SMS_ID
100000081187
Created by admin on Fri Dec 15 17:40:07 GMT 2023 , Edited by admin on Fri Dec 15 17:40:07 GMT 2023
PRIMARY