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
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
Biological effects of hormone replacement therapy in relation to serum estradiol levels.
2001
Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women.
2001
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone.
2001
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice.
2001
On call. My wife's doctor gave her Premarin for her cholesterol. I know it's a female hormone, but my cholesterol is also high, and I wonder if it could help me, too.
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
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1).
2001 Apr
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
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
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
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.
2001 Apr 20
Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome.
2001 Aug 9
Dietary oleoyl-estrone delays the growth rate of young rats.
2001 Feb
Effects of estrone sulfate alone or with medroxyprogesterone acetate on serum lipoprotein levels in postmenopausal women.
2001 Jan
Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins.
2001 Jan
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.
2001 Jan 30
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.
2001 Jul
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.
2001 Jul-Aug
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men.
2001 Jun
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.
2001 Jun
Fecal analysis of ovarian cycles in female black-handed spider monkeys (Ateles geoffroyi).
2001 Jun
Serum levels of C-reactive protein are associated with obesity, weight gain, and hormone replacement therapy in healthy postmenopausal women.
2001 Jun 1
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1.
2001 Jun 15
Daily oral oleoyl-estrone gavage induces a dose-dependent loss of fat in Wistar rats.
2001 Mar
Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.
2001 Mar 19
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.
2001 Mar-Apr
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.
2001 May
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.
2001 May
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.
2001 May
Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells.
2001 May
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.
2001 May 1
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism.
2001 May 15
A polymorphism in CYP17 and endometrial cancer risk.
2001 May 15
Serum hormones and the alcohol-breast cancer association in postmenopausal women.
2001 May 2
Arginine 454 and lysine 370 are essential for the anion specificity of the organic anion transporter, rOAT3.
2001 May 8
Effect of transforming growth factor-beta1, insulin-like growth factor-I and insulin-like growth factor-II on cell growth and oestrogen metabolism in human breast cancer cell lines.
2001 Nov
Regulation of human apolipoprotein A-I gene expression by equine estrogens.
2001 Nov
Tibolone: a compound with tissue specific inhibitory effects on sulfatase.
2001 Oct 25
Polymorphisms in OATP-C: identification of multiple allelic variants associated with altered transport activity among European- and African-Americans.
2001 Sep 21
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe.
2002
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).
2002 Apr
Peripheral changes in estrone sulfate concentration during the first trimester of gestation in cattle: comparison with unconjugated estrogens and relationship to fetal number.
2002 Apr 15
Influence of letrozole and anastrozole on total body aromatization and plasma estrogen levels in postmenopausal breast cancer patients evaluated in a randomized, cross-over study.
2002 Feb 1
Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer.
2002 Jan
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.
2002 Jul
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition.
2002 Jul 16
A new route to (+)-estrone using a bicyclo[3.2.1]octane chiral building block.
2003 Jan
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.
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
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LIVERTOX 376
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LOINC 13739-8
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WHO-ATC G03CA07
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LOINC 22663-9
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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
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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
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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
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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
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PRIMARY
SMS_ID
100000082364
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PRIMARY
ECHA (EC/EINECS)
200-164-5
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PRIMARY
IUPHAR
2818
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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
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PRIMARY
PUBCHEM
5870
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PRIMARY
INN
407
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PRIMARY
CHEBI
17263
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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
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PRIMARY
RS_ITEM_NUM
1255001
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PRIMARY
EPA CompTox
DTXSID4022367
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PRIMARY