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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H32O
Molecular Weight 288.4682
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYLESTRENOL

SMILES

CC[C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CCCC[C@]4([H])[C@@]3([H])CC[C@@]21C)O

InChI

InChIKey=AOXRBFRFYPMWLR-XGXHKTLJSA-N
InChI=1S/C20H32O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h6,15-18,21H,3-5,7-13H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including http://www.eje-online.org/content/39/3_Suppl/S124.short | https://www.ncbi.nlm.nih.gov/pubmed/8528708 | http://mspace.lib.umanitoba.ca/xmlui/bitstream/handle/1993/14464/Boux_the_Disposition.pdf?sequence=1&isAllowed=y

Ethylestrenol (INN, USAN, BAN) (brand names Maxibolin, Orabolin), or ethylnandrol (JAN), also known as 17α-ethyl ester-4-en-17β-ol or as 3-deketo-17α-ethyl-19-nortestosterone, is an anabolic-androgenic steroid (AAS) with some progestogenic activity, and low androgenic activity. It is a 17α-ethylated derivative of nandrolone and lacks the 3-keto group. It was described in the literature in 1959 and approved in 1964 for testosterone deficiency in male patients.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
37.9 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAXIBOLIN

Approved Use

Unknown

Launch Date

-1.76601596E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.53 day
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHYLESTRENOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
yes
Tox targets
PubMed

PubMed

TitleDatePubMed
Microbial oxidation of anabolic steroids.
2008
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Patents

Patents

Sample Use Guides

Male Wistar rats were trained in a one-trial-learning passive avoidance task. Ethylestrenol (1 ng, 10 ng, 100 ng, 1000 ng, or 10 mkg) was given immediately after the training trial or 1 h before the first retention test. Retention tests were given both 24 h and 48 h after acquisition. Ethylestrenol at all doses improved retention under the low footshock conditions. In groups trained with the higher footshock, the steroid-treated groups performed no better than the vehicle controls.
Route of Administration: Oral
Yeast from mid-log phase growth was diluted to OD600 = 1.0 in selective medium. Diluted yeast cultures were treated with steroid concentrations ranging from 0.01 nM to 10 mM (in a final volume of 5mkl). Following incubation yeast was lysed and assayed for beta-galactosidase activity.
Name Type Language
ETHYLESTRENOL
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
19-NORPREGN-4-EN-17-OL, (17.ALPHA.)
Common Name English
ETHYLESTRENOL [INN]
Common Name English
19-NOR-17.ALPHA.-PREGN-4-EN-17.BETA.-OL
Common Name English
NSC-37726
Code English
ETHYLESTRENOL [USAN]
Common Name English
ETHYLESTRENOL [MART.]
Common Name English
ORABOLIN
Brand Name English
ETHYLESTRENOL [VANDF]
Common Name English
ETHYLNANDROL [JAN]
Common Name English
ETHYLNANDROL
JAN  
Common Name English
ETHYLESTRENOL [HSDB]
Common Name English
ETHYLESTRENOL [MI]
Common Name English
DURABORAL
Brand Name English
ETHYLESTRENOL [ORANGE BOOK]
Common Name English
MAXIBOLIN
Brand Name English
ETHYLESTRENOL [WHO-DD]
Common Name English
DURABOLIN-O
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C2360
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
WHO-ATC A14AB02
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
WHO-VATC QA14AB02
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
DEA NO. 4000
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1094
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
CAS
965-90-2
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
DRUG BANK
DB01493
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
WIKIPEDIA
ETHYLESTRENOL
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
RXCUI
4162
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY RxNorm
MESH
D005032
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
IUPHAR
6948
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
213-523-6
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
EPA CompTox
965-90-2
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
NCI_THESAURUS
C65568
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200623
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
MERCK INDEX
M5130
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY Merck Index
EVMPD
SUB07291MIG
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
FDA UNII
ADC79EK5Q8
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
PUBCHEM
13765
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
HSDB
3327
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY
INN
1107
Created by admin on Sat Jun 26 16:16:19 UTC 2021 , Edited by admin on Sat Jun 26 16:16:19 UTC 2021
PRIMARY