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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O2
Molecular Weight 270.3668
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRONE

SMILES

C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])CCC1=O)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

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
Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells.
2000 Jan-Feb
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene.
2000 Nov
Potential fertility--defining the window of opportunity.
2001
Trial protocol and sample result of a study comparing the Clearplan Easy Fertility Monitor with serum hormone and vaginal ultrasound measurements in the determination of ovulation.
2001
Home monitoring with the ClearPlan Easy Fertility Monitor for fertility awareness.
2001
Effects of testosterone precursor supplementation on intensive weight training.
2001 Apr
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1).
2001 Apr
19-Oxygenation of C19-steroids with an A, B-ring enone structure, competitive inhibitors of estrogen biosynthesis, with human placental aromatase.
2001 Apr
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women.
2001 Apr
Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3.
2001 Apr 15
Estrogen and androgen influence hypothalamic AVP and CRF concentrations in fetal and adult sheep.
2001 Apr 2
Cholesterol sulfate: a new adhesive molecule for platelets.
2001 Apr 24
Synthesis and biological evaluation of two new radiolabelled estrogens: [125I](E)-3-methoxy-17alpha-iodovinylestra-1,3,5(10),6-tetraen-17beta-ol and.
2001 Feb
Periovulatory changes in catfish ovarian oestradiol-17beta, oestrogen-2-hydroxylase and catechol-O-methyltransferase during GnRH analogue-induced ovulation and in vitro induction of oocyte maturation by catecholoestrogens.
2001 Feb
Predominant 4-hydroxylation of estradiol by constitutive cytochrome P450s in the female ACI rat liver.
2001 Feb
Differential in vitro suppressive effects of steroids on leukocyte phagocytosis in two teleosts, tilapia and common carp.
2001 Feb
Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.
2001 Feb
The human estrogen receptor alpha dimer binds a single SRC-1 coactivator molecule with an affinity dictated by agonist structure.
2001 Feb 23
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.
2001 Feb 28
Bioequivalence and relative bioavailability of three estradiol and norethisterone acetate-containing hormone replacement therapy tablets.
2001 Jan
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.
2001 Jan
Evolution of 17beta-HSD type 4, a multifunctional protein of beta-oxidation.
2001 Jan 22
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.
2001 Jan 22
Mechanisms of estradiol inactivation in primate endometrium.
2001 Jan 22
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3).
2001 Jan 22
Non-steroidal and steroidal sulfamates: new drugs for cancer therapy.
2001 Jan 22
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.
2001 Jan 22
Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung.
2001 Jan 22
Structure and function of 17beta-hydroxysteroid dehydrogenase type 1 and type 2.
2001 Jan 22
Estrogen metabolism and malignancy: analysis of the expression and function of 17beta-hydroxysteroid dehydrogenases in colonic cancer.
2001 Jan 22
Beneficial effects of pravastatin in peri- and postmenopausal hyperlipidemic women: a 5-year study on serum lipid and sex hormone levels.
2001 Jan 31
Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells.
2001 Jan 9
The selective estrogen enzyme modulator (SEEM) in breast cancer.
2001 Jan-Mar
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.
2001 Jul
Menopausal experiences and bone density of Mayan women in Yucatan, Mexico.
2001 Jul-Aug
Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female.
2001 Jun
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.
2001 Jun
Fecal analysis of ovarian cycles in female black-handed spider monkeys (Ateles geoffroyi).
2001 Jun
[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers].
2001 Mar
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.
2001 Mar
Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary.
2001 Mar
Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes.
2001 Mar
Novel inhibitors of the enzyme estrone sulfatase (ES).
2001 Mar 26
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.
2001 Mar-Apr
Urinary excretion pattern of catecholestrogens in preovulatory LH surge during the 4-day estrous cycle of rats.
2001 May
In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide.
2001 May
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.
2001 May
Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells.
2001 May
A polymorphism in CYP17 and endometrial cancer risk.
2001 May 15
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women.
2001 May-Jun
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
5 pellets 3 times a day until symptoms are relieved
Route of Administration: Oral
Study was designed to discover filovirus entry inhibitors in a drug library of commercial medicines. One thousand and six hundred drugs were screened using the ZEBOV-GP/HIV model, a pseudovirus formed by an HIV-core packed with the Zaire Ebola virus glycoprotein. Was identified 12 gonadal hormone drugs with inhibitory activities in ZEBOV-GP/HIV entry at final concentration of 10 μmol x L(-1). One of them with moderate activity was estrone IC50: 6.87 ± 0.03 μmol-L1
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
THEELIN
Brand Name English
ESTRONE [USP]
Common 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
ESTRADIOL HEMIHYDRATE SPECIFIED IMPURITY A [EP]
Common Name English
KETOHYDROXYESTRIN
Common Name English
ESTRADIOL METABOLITE E1
Common Name English
FOLLICULAR HORMONE
Common Name English
ESTRONE [WHO-DD]
Common Name English
TOKOKIN
Common Name English
ETHINYLESTRADIOL SPECIFIED IMPURITY C [EP]
Common Name English
ESTRADIOL HEMIHYDRATE IMPURITY A [EP]
Common Name English
ESTRONE [ORANGE BOOK]
Common Name English
ETHINYLESTRADIOL IMPURITY C [EP]
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
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-HYDROXY-
Systematic 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 Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
LOINC 2258-2
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
LIVERTOX 376
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LOINC 13739-8
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WHO-ATC G03CA07
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
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
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
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
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
WHO-ATC G03CC04
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
LOINC 14160-6
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
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 Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
WHO-VATC QG03CA07
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
CFR 21 CFR 862.1280
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
WHO-VATC QG03CC04
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
Code System Code Type Description
WIKIPEDIA
ESTRONE
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
CAS
53-16-7
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
FDA UNII
2DI9HA706A
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL1405
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
NCI_THESAURUS
C484
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
EVMPD
SUB07251MIG
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
DRUG CENTRAL
3188
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-164-5
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
IUPHAR
2818
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
HSDB
3324
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
MESH
D004970
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
PUBCHEM
5870
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
USP_CATALOG
1255001
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY USP-RS
INN
407
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
RXCUI
4103
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M5033
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00655
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY
EPA CompTox
53-16-7
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
PRIMARY