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

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
Diagnostic
Diagnostic
Diagnostic
Diagnostic
Diagnostic
Diagnostic
Diagnostic
Diagnostic
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
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
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice.
2001
Effects of testosterone precursor supplementation on intensive weight training.
2001 Apr
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1).
2001 Apr
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
2001 Apr
Effects of oral and transdermal estrogen replacement therapy on markers of coagulation, fibrinolysis, inflammation and serum lipids and lipoproteins in postmenopausal women.
2001 Apr
Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin.
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
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
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.
2001 Apr 20
Cholesterol sulfate: a new adhesive molecule for platelets.
2001 Apr 24
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).
2001 Apr 9
4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout.
2001 Feb
Estrogenic potency of chemicals detected in sewage treatment plant effluents as determined by in vivo assays with Japanese medaka (Oryzias latipes).
2001 Feb
Dietary oleoyl-estrone delays the growth rate of young rats.
2001 Feb
Plasma beta-endorphin levels in obese and non-obese patients with polycystic ovary disease.
2001 Feb
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
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.
2001 Jan 30
Characteristics of cystic breast disease with special regard to breast cancer development.
2001 Jan-Feb
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
Association of genetic polymorphisms in UGT1A1 with breast cancer and plasma hormone levels.
2001 Jun
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men.
2001 Jun
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.
2001 Jun
Fecal analysis of ovarian cycles in female black-handed spider monkeys (Ateles geoffroyi).
2001 Jun
Serum levels of C-reactive protein are associated with obesity, weight gain, and hormone replacement therapy in healthy postmenopausal women.
2001 Jun 1
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1.
2001 Jun 15
[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
Daily oral oleoyl-estrone gavage induces a dose-dependent loss of fat in Wistar rats.
2001 Mar
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men.
2001 Mar
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
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.
2001 May
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.
2001 May
Effects of transdermal testosterone on bone and muscle in older men with low bioavailable testosterone levels.
2001 May
Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells.
2001 May
Pharmacologic, but not dietary, genistein supports endometriosis in a rat model.
2001 May
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
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism.
2001 May 15
A polymorphism in CYP17 and endometrial cancer risk.
2001 May 15
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction.
2001 May 15
Serum hormones and the alcohol-breast cancer association in postmenopausal women.
2001 May 2
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.
2001 May-Jun
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
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 13739-8
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 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
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 34297-2
Created by admin on Sat Jun 26 14:07:30 UTC 2021 , Edited by admin on Sat Jun 26 14:07:30 UTC 2021
LOINC 34299-8
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 31177-9
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 862.1430
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
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 2257-4
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 6776-9
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 35208-8
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 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
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 2260-8
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 2262-4
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 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