U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H32O
Molecular Weight 288.4675
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYLESTRENOL

SMILES

CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3CC[C@]12C

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

1964
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
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
ORABOLIN
Preferred Name English
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?-pregn-4-en-17?-ol
Common Name English
NSC-37726
Code English
ETHYLESTRENOL [USAN]
Common Name English
ETHYLESTRENOL [MART.]
Common Name English
ETHYLESTRENOL [VANDF]
Common Name English
ETHYLNANDROL [JAN]
Common Name English
ETHYLNANDROL
JAN  
Common Name English
ETHYLESTRENOL [HSDB]
Common Name English
Ethylestrenol [WHO-DD]
Common Name English
ETHYLESTRENOL [MI]
Common Name English
DURABORAL
Brand Name English
ETHYLESTRENOL [ORANGE BOOK]
Common Name English
MAXIBOLIN
Brand Name English
DURABOLIN-O
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C2360
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
WHO-ATC A14AB02
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
WHO-VATC QA14AB02
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
DEA NO. 4000
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
Code System Code Type Description
DRUG CENTRAL
1094
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
CAS
965-90-2
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
DRUG BANK
DB01493
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
WIKIPEDIA
ETHYLESTRENOL
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
CHEBI
31578
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
RXCUI
4162
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY RxNorm
MESH
D005032
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
IUPHAR
6948
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
NSC
37726
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
ECHA (EC/EINECS)
213-523-6
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
EPA CompTox
DTXSID6023024
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
NCI_THESAURUS
C65568
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
SMS_ID
100000082069
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
ChEMBL
CHEMBL1200623
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
MERCK INDEX
m5130
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY Merck Index
EVMPD
SUB07291MIG
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
FDA UNII
ADC79EK5Q8
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
PUBCHEM
13765
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
HSDB
3327
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY
INN
1107
Created by admin on Mon Mar 31 18:16:49 GMT 2025 , Edited by admin on Mon Mar 31 18:16:49 GMT 2025
PRIMARY