ESTRONE

First marketed in 1931

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 Search

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

Description
Sources: https://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/ja00536a023https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031
Curator's Comment: description was created based on several sources, including http://www.drugbank.ca/drugs/DB00655 https://www.ncbi.nlm.nih.gov/pubmed/2011412 https://www.ncbi.nlm.nih.gov/pubmed/17943537

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6863279 \| https://www.ncbi.nlm.nih.gov/pubmed/15081034	Agonist 2637		7.0 nM [EC50]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412	Agonist 2637

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 426 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 177 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Obesity 204 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 8307	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 8307	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 8307	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 651	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 1670	substrate 985		inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 383 P-gp 1491 UGT1A10 289 UGT1A3 421 UGT2A1 32 CYP1A1 344 CYP1A2 1013 CYP2B6 648 CYP2E1 633	P-gp 252

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1588	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A10 289	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	major
CYP1A2 1013	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	no
UGT1A3 421	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
UGT2A1 32	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
CYP1A1 344	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2B6 648	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2C9 985	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes
CYP2E1 633	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP3A5 383	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/9635876/	yes
P-gp 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes
CYP3A4 1670	substrate 3264 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 1603	inhibitor 1584 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
Reproducibility of plasma and urinary sex hormone levels in premenopausal women over a one-year period.	1999 Dec	10613337
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.	2000 Feb 11	10660625
Biological effects of hormone replacement therapy in relation to serum estradiol levels.	2001	11815726
Estrogen sulfamates: a new approach to oral estrogen therapy.	2001	11800168
Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women.	2001	11588903
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
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.	2001 Apr 20	11306210
Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines.	2001 Apr 20	11278596
Prospective randomized study of effects of unopposed estrogen replacement therapy on markers of coagulation and inflammation in postmenopausal women.	2001 Aug	11502788
[Effects of oral administration of estrogen replacement therapy in surgical menopause].	2001 Dec	11883282
Comparison of estrogen and androgen levels after oral estrogen replacement therapy.	2001 Dec	11789085
The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase.	2001 Dec	11753757
The effects of PCB exposure and fish consumption on endogenous hormones.	2001 Dec	11748036
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	11743748
Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.	2001 Feb	11159893
Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens.	2001 Jan	11231976
Effects of estrone sulfate alone or with medroxyprogesterone acetate on serum lipoprotein levels in postmenopausal women.	2001 Jan	11152917
Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins.	2001 Jan	11123367
Sleep in menopause: differential effects of two forms of hormone replacement therapy.	2001 Jan-Feb	11201509
Early postnatal plasma concentrations of testicular steroid hormones, pubertal development, and carcass leanness as potential indicators of boar taint in market weight intact male pigs.	2001 Jul	11465375
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.	2001 Jul	11408524
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.	2001 Jul-Aug	11600235
Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female.	2001 Jun	11412285
Postischemic estrogen reduces hypoperfusion and secondary ischemia after experimental stroke.	2001 Mar	11239204
[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers].	2001 Mar	11413688
Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.	2001 May	11368557
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Urinary excretion pattern of catecholestrogens in preovulatory LH surge during the 4-day estrous cycle of rats.	2001 May	11407653
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.	2001 May 1	11301044
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	11827412
Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women.	2001 Oct	11579354
Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C.	2001 Sep	11683238
Hormone replacement therapy for cognitive function in postmenopausal women.	2002	12137675
The role of cytokines in regulating estrogen synthesis: implications for the etiology of breast cancer.	2002	11879566
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).	2002 Apr	11983489
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	12041697
Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.	2002 Aug	12175967
A randomized isoflavone intervention among premenopausal women.	2002 Feb	11867507
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	11821457
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.	2002 Jul	12142247
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.	2002 Jul 26	12011098
Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors.	2002 Mar	11948019
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.	2002 Mar 8	12005172
Interaction of human organic anion transporters with various cephalosporin antibiotics.	2002 Mar 8	11909604
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.	2002 May	12018985
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.	2002 May	12015519
Formal enantioselective synthesis of (+)-estrone.	2007 Mar 15	17295499
Catalytic asymmetric Torgov cyclization: a concise total synthesis of (+)-estrone.	2014 Aug 11	25080299

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

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

ETHINYLESTRADIOL IMPURITY C [EP IMPURITY]

Common Name

English

THEELIN

Brand Name

English

FOLLICULAR-HORMONE

Common Name

English

ESTRONE [VANDF]

Common Name

English

FOLLICULINUM

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