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
SMILES
[H][C@@]12CC[C@@](O)(CC)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCCC=C4CC[C@@]23[H]
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
Molecular Formula | C20H32O |
Molecular Weight | 288.4675 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugbank.ca/drugs/DB01493Curator'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
Sources: https://www.drugbank.ca/drugs/DB01493
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18395441 |
37.9 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | MAXIBOLIN Approved UseUnknown Launch Date1964 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.53 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7233967/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8528708
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18395441
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.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 16:01:56 GMT 2023
by
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on
Fri Dec 15 16:01:56 GMT 2023
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Record UNII |
ADC79EK5Q8
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C2360
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WHO-ATC |
A14AB02
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WHO-VATC |
QA14AB02
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DEA NO. |
4000
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1094
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965-90-2
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DB01493
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ETHYLESTRENOL
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31578
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4162
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D005032
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6948
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37726
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213-523-6
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DTXSID6023024
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C65568
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100000082069
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CHEMBL1200623
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m5130
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SUB07291MIG
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ADC79EK5Q8
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13765
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3327
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1107
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Related Record | Type | Details | ||
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ACTIVE MOIETY |