U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O2
Molecular Weight 270.3661
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRONE

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

InChI

InChIKey=DNXHEGUUPJUMQT-CBZIJGRNSA-N
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H22O2
Molecular Weight 270.3661
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Curator's Comment: Estrone sulfate crossed the blood brain barrier in rats.

Originator

Curator's Comment: Estrone is one of the hormones responsible for sexual development and function in females.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Primary
Estragyn

Approved Use

Estragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms. Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma.
Primary
Estragyn

Approved Use

Estragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms. Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma.
Primary
THEELIN

Approved Use

For management of Menopausal and postmenopausal disorders
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
733 pg/mL
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
550 pg × h/mL
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Reproducibility of plasma and urinary sex hormone levels in premenopausal women over a one-year period.
1999 Dec
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone.
2001
Home monitoring with the ClearPlan Easy Fertility Monitor for fertility awareness.
2001
Futile cycling of estrone sulfate and estrone in the recirculating perfused rat liver preparation.
2001 Apr
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.
2001 Apr
Effects of testosterone precursor supplementation on intensive weight training.
2001 Apr
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
2001 Apr
Effects of oral and transdermal estrogen replacement therapy on markers of coagulation, fibrinolysis, inflammation and serum lipids and lipoproteins in postmenopausal women.
2001 Apr
Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin.
2001 Apr
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women.
2001 Apr
Measurement of urinary and fecal steroid metabolites during the ovarian cycle in captive and wild Japanese macaques, Macaca fuscata.
2001 Apr
Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3.
2001 Apr 15
Do urinary estrogen metabolites reflect the differences in breast cancer risk between Singapore Chinese and United States African-American and white women?
2001 Apr 15
Structural and functional consequences of inactivation of human glutathione S-transferase P1-1 mediated by the catechol metabolite of equine estrogens, 4-hydroxyequilenin.
2001 Apr 17
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.
2001 Apr 20
Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines.
2001 Apr 20
Cholesterol sulfate: a new adhesive molecule for platelets.
2001 Apr 24
Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases.
2001 Dec
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.
2001 Feb
Estrogenic potency of chemicals detected in sewage treatment plant effluents as determined by in vivo assays with Japanese medaka (Oryzias latipes).
2001 Feb
Plasma beta-endorphin levels in obese and non-obese patients with polycystic ovary disease.
2001 Feb
Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens.
2001 Jan
Sleep in menopause: differential effects of two forms of hormone replacement therapy.
2001 Jan-Feb
The selective estrogen enzyme modulator (SEEM) in breast cancer.
2001 Jan-Mar
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.
2001 Jun
Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys.
2001 Jun 15
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men.
2001 Mar
Can variability in the hormonal status of elderly women assist in the decision to administer estrogens?
2001 Mar
Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease.
2001 Mar
Determination of steroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by fully automated on-line solid-phase extraction-liquid chromatography-diode array detection.
2001 Mar 16
Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.
2001 May
Actions of the soy phytoestrogen genistein in models of human chronic disease: potential involvement of transforming growth factor beta.
2001 May
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.
2001 May
Pharmacologic, but not dietary, genistein supports endometriosis in a rat model.
2001 May
2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells.
2001 May
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.
2001 May 1
A polymorphism in CYP17 and endometrial cancer risk.
2001 May 15
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.
2001 May-Jun
Endocrinology of gynaecomastia.
2001 Nov
Tibolone: a compound with tissue specific inhibitory effects on sulfatase.
2001 Oct 25
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe.
2002
A randomized isoflavone intervention among premenopausal women.
2002 Feb
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.
2002 Jul
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.
2002 Jun
Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors.
2002 Mar
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta.
2002 Mar
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.
2002 Mar 8
Interaction of human organic anion transporters with various cephalosporin antibiotics.
2002 Mar 8
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.
2002 May
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Vaginal route is possible: The recommended dose is 2.0 to 4.0 g intravaginally per day, adjusted to the lowest amount that controls symptoms http://www.rxlist.com/estragyn-drug.htm
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
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
Created
by admin
on Thu Jul 06 21:34:07 UTC 2023
Edited
by admin
on Thu Jul 06 21:34:07 UTC 2023
Record UNII
2DI9HA706A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRONE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
ESTRONE [MI]
Common Name English
WAY 164397
Code English
1,3,5-ESTRATRIEN-3-OL-17-ONE
Common Name English
estrone [INN]
Common Name English
FOLLICULIN
Common Name English
ETHINYLESTRADIOL IMPURITY C [EP IMPURITY]
Common Name English
THEELIN
Brand Name English
FOLLICULAR-HORMONE
Common Name English
ESTRONE [VANDF]
Common Name English
FOLLICULINUM
HPUS  
Common Name English
OESTRONE
Common Name English
THELYKININ
Common Name English
KETOHYDROXYESTRIN
Common Name English
ESTRADIOL METABOLITE E1
Common Name English
FOLLICULAR HORMONE
Common Name English
TOKOKIN
Common Name English
ESTRONE [ORANGE BOOK]
Common Name English
FOLLICULINUM [HPUS]
Common Name English
ESTRONE [USP-RS]
Common Name English
ESTRONE [MART.]
Common Name English
ESTRONE [JAN]
Common Name English
3-HYDROXYESTRA-1,3,5(10)-TRIEN-17-ONE
Systematic Name English
ESTROGENIC SUBSTANCE
Brand Name English
ESTRADIOL HEMIHYDRATE IMPURITY A [EP IMPURITY]
Common Name English
Estrone [WHO-DD]
Common Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-HYDROXY-
Systematic Name English
ESTRONE [USP MONOGRAPH]
Common Name English
ESTRONE [HSDB]
Common Name English
(8R,9S,13S,14S)-3-HYDROXY-13-METHYL-6,7,8,9,11,12,13,14,15,16-DECAHYDRO-17H-CYCLOPENTA(A)PHENANTHREN-17-ONE
Systematic Name English
NSC-9699
Code English
Classification Tree Code System Code
LOINC 25403-7
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
LOINC 2258-2
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
LIVERTOX 376
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LOINC 13739-8
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
WHO-ATC G03CA07
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
LOINC 22663-9
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
LOINC 34297-2
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LOINC 34299-8
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LOINC 31177-9
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CFR 21 CFR 862.1430
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
LOINC 27998-4
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LOINC 2257-4
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LOINC 6776-9
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LOINC 35208-8
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LOINC 2261-6
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WHO-ATC G03CC04
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
LOINC 14160-6
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LOINC 34298-0
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LOINC 2260-8
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LOINC 2262-4
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LOINC 2259-0
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
WHO-VATC QG03CA07
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
CFR 21 CFR 862.1280
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
WHO-VATC QG03CC04
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
Code System Code Type Description
WIKIPEDIA
ESTRONE
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
CAS
53-16-7
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
FDA UNII
2DI9HA706A
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
ChEMBL
CHEMBL1405
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
DAILYMED
2DI9HA706A
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
NCI_THESAURUS
C484
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
EVMPD
SUB07251MIG
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
NSC
9699
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
DRUG CENTRAL
3188
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
SMS_ID
100000082364
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-164-5
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
IUPHAR
2818
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
WIKIPEDIA
Estrone (medication)
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
HSDB
3324
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
MESH
D004970
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
PUBCHEM
5870
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
INN
407
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
CHEBI
17263
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
RXCUI
4103
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M5033
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB00655
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
RS_ITEM_NUM
1255001
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID4022367
Created by admin on Thu Jul 06 21:34:09 UTC 2023 , Edited by admin on Thu Jul 06 21:34:09 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE LESS ACTIVE -> PARENT
IN-VITRO
Scientific Literature
PARENT -> METABOLITE
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
METABOLITE -> PARENT
IN-VITRO
Scientific Literature
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
USP
Related Record Type Details
ACTIVE MOIETY