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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
Efficient oxidizing methods for the synthesis of oxandrolone intermediates.
2004 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
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 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
WIKIPEDIA Designer-drugs-Mestanolone
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
Code System Code Type Description
FDA UNII
S712YZ168E
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY
CAS
521-11-9
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-302-6
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PRIMARY
MERCK INDEX
m7255
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY Merck Index
MESH
C008376
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL261514
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PRIMARY
DRUG CENTRAL
3341
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PRIMARY
EPA CompTox
DTXSID0048973
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PRIMARY
PUBCHEM
10633
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY
NCI_THESAURUS
C83939
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY
NSC
18219
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY
INN
862
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY
EVMPD
SUB08789MIG
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY
SMS_ID
100000081187
Created by admin on Fri Dec 15 17:40:07 UTC 2023 , Edited by admin on Fri Dec 15 17:40:07 UTC 2023
PRIMARY