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
Biological effects of hormone replacement therapy in relation to serum estradiol levels.	2001	11815726
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution.	2001	11721885
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
Structural and functional consequences of inactivation of human glutathione S-transferase P1-1 mediated by the catechol metabolite of equine estrogens, 4-hydroxyequilenin.	2001 Apr 17	11294649
Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines.	2001 Apr 20	11278596
Cholesterol sulfate: a new adhesive molecule for platelets.	2001 Apr 24	11319189
Prospective randomized study of effects of unopposed estrogen replacement therapy on markers of coagulation and inflammation in postmenopausal women.	2001 Aug	11502788
Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome.	2001 Aug 9	11483057
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	11751102
The effects of PCB exposure and fish consumption on endogenous hormones.	2001 Dec	11748036
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
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
Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins.	2001 Jan	11123367
Paradoxical effect of estradiol: it can block its own bioformation in human breast cancer cells.	2001 Jul	11530280
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.	2001 Jun	11409947
Serum lipid profile improved by ultra-low doses of 17 beta-estradiol in elderly women.	2001 Jun	11397883
Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes.	2001 Mar	11181504
Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.	2001 Mar 19	11267661
Actions of the soy phytoestrogen genistein in models of human chronic disease: potential involvement of transforming growth factor beta.	2001 May	11356157
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.	2001 May	11350888
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Serum hormones and the alcohol-breast cancer association in postmenopausal women.	2001 May 2	11333294
Arginine 454 and lysine 370 are essential for the anion specificity of the organic anion transporter, rOAT3.	2001 May 8	11331016
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women.	2001 May-Jun	11355042
Regulation of human apolipoprotein A-I gene expression by equine estrogens.	2001 Nov	11714848
Micronized progesterone regulation of the endometrial glandular cycling pool.	2001 Oct	11603222
Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women.	2001 Oct	11579354
[Prevention and treatment of recurrent urinary system infection with estrogen cream in postmenopausal women].	2001 Sep	11769665
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
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
Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies.	2002 Apr 17	11959894
A randomized isoflavone intervention among premenopausal women.	2002 Feb	11867507
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	11748225
Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer.	2002 Jan	11860358
Mammary secretion of oestrogens in the cow.	2002 Jul	12142232
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition.	2002 Jul 16	12102636
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.	2002 Jun	12042670
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer.	2002 Mar	11895893
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta.	2002 Mar	11861502
Specific radioimmunoassay of estrone sulfate. Application to measurement in male plasma.	2002 May	12127046
The choice of hormone replacement therapy or statin therapy in the treatment of hyperlipidemic postmenopausal women.	2002 May	12044587
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.	2002 May	12018985
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.	2002 May	11981753
A new route to (+)-estrone using a bicyclo[3.2.1]octane chiral building block.	2003 Jan	12520140

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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EP

Amount:


					CXY7B3Q98Z

ESTRADIOL HEMIHYDRATE

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