ESTRONE

First marketed in 1931

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 Search

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

Molecular Formula	C18H22O2
Molecular Weight	270.3668
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttp://www.drugfuture.com/chemdata/estrone.html | http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsat | http://pubs.acs.org/doi/abs/10.1021/ja00536a023
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 123 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6863279 \| https://www.ncbi.nlm.nih.gov/pubmed/15081034	Agonist 2470		7.0 nM [EC50]
Estrogen receptor alpha 123 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412	Agonist 2470

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 411 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Benign breast disease 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Endometrial cancer 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Prostate cancer 159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Obesity 194 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Infertility 14 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Amenorrhea 18 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Ovarian diseases 7 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Precocious puberty 8 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Menopausal and postmenopausal disorder 10 Sources: http://www.rxlist.com/estragyn-drug.htm http://chealth.canoe.com/drug/getdrug/estragyn-vaginal-cream https://www.drugs.com/international/estrone.html	Primary	Approved 8043	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.
Endometrial hyperplasia/carcinoma 7 Sources: http://www.rxlist.com/estragyn-drug.htm http://chealth.canoe.com/drug/getdrug/estragyn-vaginal-cream https://www.drugs.com/international/estrone.html	Primary	Approved 8043	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.
Menopausal and postmenopausal disorders 7 Sources: http://www.druglib.com/activeingredient/estrone/	Primary	Approved 8043	THEELIN Approved Use For management of Menopausal and postmenopausal disorders
Premenstrual syndrome 37 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031	Palliative	Phase III 643	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
733 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/	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

Value	Dose	Co-administered	Analyte	Population
550 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/	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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1601	substrate 936		inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 367 P-gp 1400 UGT1A10 273 UGT1A3 397 UGT2A1 31 CYP1A1 325 CYP1A2 972 CYP2B6 616 CYP2E1 606	P-gp 248

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1514	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A10 273	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	major
CYP1A2 972	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	no
UGT1A3 397	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
UGT2A1 31	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
CYP1A1 325	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2B6 616	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2C9 936	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes
CYP2E1 606	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP3A5 367	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9635876/	yes
P-gp 1400	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes
CYP3A4 1601	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes	weak (co-administration study) Comment: Coadministration with ketoconazole (CYP3A4 inhibitor) resulted in estrone expsoure increase of ~1.4 foold Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1507	inhibitor 1489 Sources: https://pubmed.ncbi.nlm.nih.gov/19129680/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:17263	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17263
ChemicalBook	CB5741416	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5741416
MolPort	MolPort-001-742-529	https://www.molport.com/shop/molecule-link/MolPort-001-742-529
Selleck Chemicals	Estrone	http://www.selleckchem.com/products/Estrone.html
ZINC	ZINC000013509425	http://zinc15.docking.org/substances/ZINC000013509425
eMolecules	29543531	https://www.emolecules.com/cgi-bin/more?vid=29543531
eMolecules	511617	https://www.emolecules.com/cgi-bin/more?vid=511617

PubMed

Title	Date	PubMed
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice.	2001	11409300
Effects of testosterone precursor supplementation on intensive weight training.	2001 Apr	11403114
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1).	2001 Apr	11358677
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.	2001 Apr	11352550
Effects of oral and transdermal estrogen replacement therapy on markers of coagulation, fibrinolysis, inflammation and serum lipids and lipoproteins in postmenopausal women.	2001 Apr	11341495
Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin.	2001 Apr	11305597
19-Oxygenation of C19-steroids with an A, B-ring enone structure, competitive inhibitors of estrogen biosynthesis, with human placental aromatase.	2001 Apr	11305590
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women.	2001 Apr	11294513
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	11309288
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.	2001 Apr 20	11306210
Cholesterol sulfate: a new adhesive molecule for platelets.	2001 Apr 24	11319189
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).	2001 Apr 9	11294387
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.	2001 Feb	11398990
4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout.	2001 Feb	11351435
Estrogenic potency of chemicals detected in sewage treatment plant effluents as determined by in vivo assays with Japanese medaka (Oryzias latipes).	2001 Feb	11351429
Dietary oleoyl-estrone delays the growth rate of young rats.	2001 Feb	11315501
Hormone contents in peripheral tissues after correct and off-label use of growth promoting hormones in cattle: effect of the implant preparations Filaplix-H, Raglo, Synovex-H and Synovex Plus.	2001 Jan	11297194
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.	2001 Jan 30	11306082
Characteristics of cystic breast disease with special regard to breast cancer development.	2001 Jan-Feb	11299838
The selective estrogen enzyme modulator (SEEM) in breast cancer.	2001 Jan-Mar	11384867
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.	2001 Jul	11408524
Menopausal experiences and bone density of Mayan women in Yucatan, Mexico.	2001 Jul-Aug	11400221
Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female.	2001 Jun	11412285
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.	2001 Jun	11409947
Association of genetic polymorphisms in UGT1A1 with breast cancer and plasma hormone levels.	2001 Jun	11401924
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men.	2001 Jun	11397902
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.	2001 Jun	11397849
Fecal analysis of ovarian cycles in female black-handed spider monkeys (Ateles geoffroyi).	2001 Jun	11376446
Serum levels of C-reactive protein are associated with obesity, weight gain, and hormone replacement therapy in healthy postmenopausal women.	2001 Jun 1	11390329
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1.	2001 Jun 15	11389699
[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers].	2001 Mar	11413688
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.	2001 Mar	11355746
Daily oral oleoyl-estrone gavage induces a dose-dependent loss of fat in Wistar rats.	2001 Mar	11323446
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men.	2001 Mar	11303585
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.	2001 Mar-Apr	11371017
Urinary excretion pattern of catecholestrogens in preovulatory LH surge during the 4-day estrous cycle of rats.	2001 May	11407653
In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide.	2001 May	11368553
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.	2001 May	11355334
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.	2001 May	11350888
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.	2001 May	11331656
Effects of transdermal testosterone on bone and muscle in older men with low bioavailable testosterone levels.	2001 May	11320105
Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells.	2001 May	11312142
Pharmacologic, but not dietary, genistein supports endometriosis in a rat model.	2001 May	11294976
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	11294972
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism.	2001 May 15	11369455
A polymorphism in CYP17 and endometrial cancer risk.	2001 May 15	11358812
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction.	2001 May 15	11336660
Serum hormones and the alcohol-breast cancer association in postmenopausal women.	2001 May 2	11333294
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.	2001 May-Jun	11392373
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women.	2001 May-Jun	11355042

Patents

Sample Use Guides

In Vivo Use Guide

5 pellets 3 times a day until symptoms are relieved

Route of Administration: Oral

In Vitro Use Guide

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

Substance Class	Chemical Created by `admin` on `Sat Jun 26 14:07:28 UTC 2021` Edited by `admin` on `Sat Jun 26 14:07:28 UTC 2021`
Record UNII	2DI9HA706A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESTRONE

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

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