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

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
Sources: http://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://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttps://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 2678		7.0 nM [EC50]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 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 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Obesity 203 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 8429	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 8429	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 8429	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 656	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 1737	substrate 1037		inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 395 P-gp 1537 UGT1A10 291 UGT1A3 422 UGT2A1 32 CYP1A1 349 CYP1A2 1054 CYP2B6 664 CYP2E1 667	P-gp 257

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	major
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	no
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
UGT2A1 32	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9635876/	yes
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes
CYP3A4 1737	substrate 3367 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 1647	inhibitor 1626 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
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
Involvement of genotoxic effects in the initiation of estrogen-induced cellular transformation: studies using Syrian hamster embryo cells treated with 17beta-estradiol and eight of its metabolites.	2000 Apr 1	10728588
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.	2000 Feb 11	10660625
Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women.	2001	11588903
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.	2001 Apr	11250930
Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3.	2001 Apr 15	11284723
Postmenopausal endogenous oestrogens and risk of endometrial cancer: results of a prospective study.	2001 Apr 6	11286480
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).	2001 Apr 9	11294387
Comparison of estrogen and androgen levels after oral estrogen replacement therapy.	2001 Dec	11789085
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.	2001 Feb 28	11223173
Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens.	2001 Jan	11231976
Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro.	2001 Jan	11170511
Effects of estrone sulfate alone or with medroxyprogesterone acetate on serum lipoprotein levels in postmenopausal women.	2001 Jan	11152917
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
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.	2001 Jan 22	11165020
Influence of endogenous androgens on carotid wall in postmenopausal women.	2001 Jan-Feb	11201514
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.	2001 Jul-Aug	11600235
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.	2001 Jun	11409947
Postischemic estrogen reduces hypoperfusion and secondary ischemia after experimental stroke.	2001 Mar	11239204
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.	2001 Mar	11355746
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents.	2001 Mar	11284326
Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease.	2001 Mar	11238492
Determination of steroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by fully automated on-line solid-phase extraction-liquid chromatography-diode array detection.	2001 Mar 16	11293581
Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.	2001 Mar 19	11267661
Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.	2001 Mar 2	11102445
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.	2001 Mar-Apr	11371017
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.	2001 May	11350888
Urinary excretion pattern of catecholestrogens in preovulatory LH surge during the 4-day estrous cycle of rats.	2001 May	11407653
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.	2001 May	11355334
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
Arginine 454 and lysine 370 are essential for the anion specificity of the organic anion transporter, rOAT3.	2001 May 8	11331016
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe.	2002	12006724
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
Number of years since menopause: spontaneous bone loss is dependent but response to hormone replacement therapy is independent.	2002 Apr	11934658
Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta.	2002 Apr	11932330
An evolutionarily ancient Oatp: insights into conserved functional domains of these proteins.	2002 Apr	11897630
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.	2002 Jul	12142247
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition.	2002 Jul 16	12102636
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.	2002 Jul 26	12011098
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta.	2002 Mar	11861502
Interaction of human organic anion transporters with various cephalosporin antibiotics.	2002 Mar 8	11909604
The IGF-system in healthy pre- and postmenopausal women: relations to demographic variables and sex-steroids.	2002 May	12127047
Estrogens affect endothelin-1 mRNA expression in LNCaP human prostate carcinoma cells.	2002 May	12074801
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.	2002 May	12015519
Association of CYP1B1 polymorphisms and breast cancer risk.	2002 May	12010864
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.	2002 May	11981753

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:02:46 GMT 2023` Edited by `admin` on `Sat Dec 16 16:02:46 GMT 2023`
Record UNII	2DI9HA706A
Record Status	`Validated (UNII)`
Record Version

Download

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

Created by admin on Sat Dec 16 16:02:48 GMT 2023 , Edited by admin on Sat Dec 16 16:02:48 GMT 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

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CFR

21 CFR 862.1280

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WHO-VATC

QG03CC04

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Code System Code Type Description

WIKIPEDIA

ESTRONE

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PRIMARY

CAS

53-16-7

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PRIMARY

FDA UNII

2DI9HA706A

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PRIMARY

ChEMBL

CHEMBL1405

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PRIMARY

DAILYMED

2DI9HA706A

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PRIMARY

NCI_THESAURUS

C484

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PRIMARY

EVMPD

SUB07251MIG

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PRIMARY

NSC

9699

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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)

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PRIMARY

HSDB

3324

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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

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PRIMARY

RxNorm

MERCK INDEX

m5033

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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

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PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					1S4CJB5ZGN

ESTRADIOL BENZOATE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (TLC)

Qualification:

USP

Amount:

Related Record Type Details


					2DI9HA706A

ESTRONE

ACTIVE MOIETY

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator