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 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

C[C@]12CC[C@H]3[C@@H](CCC4=CC(O)=CC=C34)[C@@H]1CCC2=O

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

Description
Curator's Comment: https://books.google.ru/books?id=Thtz7On_lhEC&pg=PA356&lpg=PA356&dq=DL-ESTRONE retrieved from The Hormones V1: Physiology, Chemistry and Applications By Gregory Pincus, Thimann Kenneth Vivian Pincus Gregory, p.356

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. Estrogens enter the cells of responsive tissues (e.g. female organs, breasts, hypothalamus, pituitary) where they interact with estrogen receptors. Hormone-bound estrogen receptors dimerize, translocate to the nucleus of cells and bind to estrogen response elements (ERE) of genes. Binding to ERE alters the transcription rate of affected genes. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) release from the anterior pituitary. Estrone dl-Form is a derivative of estrone. As early as 1935 extensive research programs directed toward the total synthesis of the female sex hormone estrone were well under way. These studies have since been continued with increasing interest in laboratories all over the world. In 1942 Bachmann, Kushner and Stevenson succeeded in synthesizing a stereoisomer of the hormone,''estrone a." Using essentially the same synthetic scheme as Bachmann, et al., Anner and Miescher were able to isolate additional stereoisomers including dl-estrone (Estrone, (+-)-Isomer) . Six of the eight possible racemic forms, estrone, a-f, have now been reported. Dl-Estrone (Estrone, (+-)-Isomer) is less active than Estrone.

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
Biological effects of hormone replacement therapy in relation to serum estradiol levels.
2001
Estrogen sulfamates: a new approach to oral estrogen therapy.
2001
[Effects of oral administration of estrogen replacement therapy in surgical menopause].
2001 Dec
Comparison of estrogen and androgen levels after oral estrogen replacement therapy.
2001 Dec
Estrogen replacement therapy after breast cancer: a 12-year follow-up.
2001 Dec
The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase.
2001 Dec
By the way, Doctor. Whenever I read about the effects of hormone replacement therapy (HRT), the researchers always seem to use 0.625 mg of Premarin. I'm taking 1 mg of Estrace daily. How does this compare to the standard dose of Premarin?
2001 Dec
The effects of PCB exposure and fish consumption on endogenous hormones.
2001 Dec
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
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
[Prevention and treatment of recurrent urinary system infection with estrogen cream in postmenopausal women].
2001 Sep
Hormone replacement therapy for cognitive function in postmenopausal women.
2002
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe.
2002
The role of cytokines in regulating estrogen synthesis: implications for the etiology of breast cancer.
2002
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).
2002 Apr
Number of years since menopause: spontaneous bone loss is dependent but response to hormone replacement therapy is independent.
2002 Apr
Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta.
2002 Apr
Bone loss at the femoral neck in premenopausal white women: effects of weight change and sex-hormone levels.
2002 Apr
An evolutionarily ancient Oatp: insights into conserved functional domains of these proteins.
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
Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies.
2002 Apr 17
Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.
2002 Aug
Hormonal measurements in late pregnancy and parturition in dairy cows--possible tools to monitor foetal well being.
2002 Aug 15
Functional characterization of the mouse organic-anion-transporting polypeptide 2.
2002 Aug 19
A randomized isoflavone intervention among premenopausal women.
2002 Feb
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
Transcellular transport of organic anions across a double-transfected Madin-Darby canine kidney II cell monolayer expressing both human organic anion-transporting polypeptide (OATP2/SLC21A6) and Multidrug resistance-associated protein 2 (MRP2/ABCC2).
2002 Feb 22
Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer.
2002 Jan
Endocrine changes in late bovine pregnancy with special emphasis on fetal well-being.
2002 Jul
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.
2002 Jul
Mammary secretion of oestrogens in the cow.
2002 Jul
Does place of birth influence endogenous hormone levels in Asian-American women?
2002 Jul 1
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition.
2002 Jul 16
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.
2002 Jul 26
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.
2002 Jun
Alveolar and postcranial bone density in postmenopausal women receiving hormone/estrogen replacement therapy: a randomized, double-blind, placebo-controlled trial.
2002 Jun 24
Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors.
2002 Mar
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer.
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
The IGF-system in healthy pre- and postmenopausal women: relations to demographic variables and sex-steroids.
2002 May
Specific radioimmunoassay of estrone sulfate. Application to measurement in male plasma.
2002 May
Estrogens affect endothelin-1 mRNA expression in LNCaP human prostate carcinoma cells.
2002 May
Effects of lactation length and an exogenous progesterone and estradiol-17beta regimen during embryo attachment on endogenous steroid concentrations and embryo survival in sows.
2002 May
The choice of hormone replacement therapy or statin therapy in the treatment of hyperlipidemic postmenopausal women.
2002 May
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.
2002 May
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.
2002 May
Association of CYP1B1 polymorphisms and breast cancer risk.
2002 May
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
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
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 07:04:09 GMT 2025
Edited
by admin
on Wed Apr 02 07:04:09 GMT 2025
Record UNII
2DI9HA706A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOLLICULINUM
HPUS  
Preferred Name English
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
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 Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
LOINC 2258-2
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
LIVERTOX 376
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LOINC 13739-8
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
WHO-ATC G03CA07
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
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
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
WHO-VATC QG03CA07
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
CFR 21 CFR 862.1280
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
WHO-VATC QG03CC04
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
Code System Code Type Description
WIKIPEDIA
ESTRONE
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
CAS
53-16-7
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
FDA UNII
2DI9HA706A
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL1405
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
DAILYMED
2DI9HA706A
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
NCI_THESAURUS
C484
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
EVMPD
SUB07251MIG
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
NSC
9699
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
DRUG CENTRAL
3188
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
SMS_ID
100000082364
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-164-5
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
IUPHAR
2818
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
WIKIPEDIA
Estrone (medication)
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
HSDB
3324
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
MESH
D004970
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
PUBCHEM
5870
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
INN
407
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
CHEBI
17263
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
RXCUI
4103
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m5033
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB00655
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
RS_ITEM_NUM
1255001
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID4022367
Created by admin on Wed Apr 02 07:04:09 GMT 2025 , Edited by admin on Wed Apr 02 07:04:09 GMT 2025
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE LESS ACTIVE -> PARENT
PARENT -> METABOLITE
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
METABOLITE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
USP
Related Record Type Details
ACTIVE MOIETY