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Details

Stereochemistry ABSOLUTE
Molecular Formula C36H54O3
Molecular Weight 534.8122
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OLEOYLESTRONE

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]3([H])C4=CC=C(OC(=O)CCCCCCC\C=C/CCCCCCCC)C=C4CC[C@@]23[H]

InChI

InChIKey=IMIPDPVHGGHVNH-YWVHRCQQSA-N
InChI=1S/C36H54O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-35(38)39-29-20-22-30-28(27-29)19-21-32-31(30)25-26-36(2)33(32)23-24-34(36)37/h10-11,20,22,27,31-33H,3-9,12-19,21,23-26H2,1-2H3/b11-10-/t31-,32-,33+,36+/m1/s1

HIDE SMILES / InChI

Molecular Formula C36H54O3
Molecular Weight 534.8122
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase. It’s used as hameopatic in management of premenopausal and postmenopausal symptoms. In 1929, Butenandt isolated estrone from the urine of pregnant women. Estrone is known to be a carcinogen for human females as well as a cause of breast tenderness or pain, nausea, headache, hypertension, and leg cramps in the context of non-endogenous exposure. In men, estrone has been known to cause anorexia, nausea, vomiting, and erectile dysfunction. Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown
Diagnostic
Unknown
Primary
Estragyn
Primary
Estragyn
Primary
THEELIN
Palliative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
733 pg/mL
0.5 mg single, vaginal
ESTRONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
550 pg × h/mL
0.5 mg single, vaginal
ESTRONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
0.5 mg single, vaginal
ESTRONE plasma
Homo sapiens

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Estrone is available in the following doses: Estrone 2 Mg/ml Intramuscular Solution Estrone 5 Mg/ml Intramuscular Solution Estrone Compounding Powder Forms of Medication Estrone is available in the following forms: Injectable Solution Injectable Suspension Vaginal Suppository
Route of Administration: Intramuscular
In Vitro Use Guide
At 1.0 x 10(-8) M, estrone promoted growth of MTW9/PL cells established from the carcinogen-induced hormone-responsive MT-W9A rat mammary tumor of a Wistar-Furth (W/Fu) rat.
Substance Class Chemical
Record UNII
64R56KMG1Z
Record Status Validated (UNII)
Record Version