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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O5S
Molecular Weight 350.4311
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRONE SULFATE

SMILES

C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])CCC1=O)OS(=O)(=O)O

InChI

InChIKey=JKKFKPJIXZFSSB-CBZIJGRNSA-N
InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1

HIDE SMILES / InChI
Molecular Formula C18H22O5S
Molecular Weight 350.4311
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: By Gregory Pincus, Thimann Kenneth Vivian Pincus Gregory, p.356

been reported. Dl-Estrone (Estrone, (+-)-Isomer) is less active than Estrone.

CNS Activity

CNS Penetrant
2415
Curator's Comment:: Estrone sulfate crossed the blood brain barrier in rats.

Originator

Anner, G.|Miescher, K.
7
Curator's Comment:: Estrone is one of the hormones responsible for sexual development and function in females.

Approval Year

1931
25
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2456
Menopausal and postmenopausal disorder
Endometrial hyperplasia/carcinoma
 7 nM [EC50]
Agonist
2456
Premenstrual syndrome
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Natural Metabolite
Diagnostic
Natural Metabolite
Diagnostic
Natural Metabolite
Diagnostic
Natural Metabolite
Diagnostic
Natural Metabolite
Diagnostic
Natural Metabolite
Diagnostic
Natural Metabolite
Diagnostic
Natural Metabolite
Diagnostic
Natural Metabolite
Primary
Estrogen receptor alpha
Approved
7997
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
Estrogen receptor alpha
Approved
7997
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
Approved
7997
THEELIN

Approved Use

For management of Menopausal and postmenopausal disorders
Palliative
Estrogen receptor alpha
Phase III
650
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1470
substrate
865
inhibitor
1360

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1223

UGT1A10
247

UGT1A3
358

UGT2A1
29

CYP1A1
302

CYP1A2
892

CYP2B6
575

CYP2E1
567

CYP3A5
346
P-gp
225
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1255
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
UGT1A10
247
 major
CYP1A2
892
 no
UGT1A3
358
 weak
UGT2A1
29
 weak
CYP1A1
302
 yes
CYP2B6
575
 yes
CYP2C9
865
 yes
CYP2E1
567
 yes
CYP3A5
346
 yes
P-gp
1223
 yes
CYP3A4
1470
 yes
weak (co-administration study)
Comment: Coadministration with ketoconazole (CYP3A4 inhibitor) resulted in estrone expsoure increase of ~1.4 foold
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1392
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:17263
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17263
MolPort
MolPort-001-742-529
https://www.molport.com/shop/molecule-link/MolPort-001-742-529
ZINC
ZINC000013509425
http://zinc15.docking.org/substances/ZINC000013509425
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
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.
2001 Feb
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
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

Patents

04824850
10
05633392
7
05763432
7
06352980
7
06541463
7
07417142
8
07893284
7
08030296
7
JP2000001415A
8
JP2000180428A
7
JP2002503696A
7
JP2004049129A
7
JP2005500299A
34
JP2008001723A
7
JP4017664B2
7
JPH02138294A
7
JPH08501286A
7
JPH10139635A
9
JPS56167700A
7
JPS6440412A
12
US4117234
7

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
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 10:22:59 UTC 2021
Edited
by admin
on Sat Jun 26 10:22:59 UTC 2021
Record UNII
QTL48N278K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRONE SULFATE
MI  
Common Name English
ESTRONE 3 SULFATE
Common Name English
ESTRONE-3-SULFATE
Common Name English
ESTRONE-3-SULPHATE
Common Name English
ESTRONE, HYDROGEN SULFATE
Common Name English
US-2917522
Code English
ESTRONE SULFATE [MI]
Common Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-(SULFOOXY)-
Systematic Name English
ESTRADIOL METABOLITE (E1S)
Common Name English
ESTRA-1,3,5 (10)-TRIENE-17-ONE-3-YL-SULFATE
Common Name English
ESTRONE BISULFATE
Common Name English
CONJUGOL
Brand Name English
PRICE
Brand Name English
ESTRONE HEMISULFATE
Common Name English
ESTRONE HYDROGEN SULFATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2181
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
LOINC 15355-1
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
Code System Code Type Description
MESH
C017296
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
NCI_THESAURUS
C1091
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
WIKIPEDIA
ESTRONE SULFATE
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-575-9
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
FDA UNII
QTL48N278K
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
IUPHAR
4749
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
CAS
481-97-0
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
DRUG BANK
DB04574
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
MERCK INDEX
M5033
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY Merck Index
EVMPD
SUB32459
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
PUBCHEM
3001028
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
DRUG CENTRAL
4857
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
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Structure of ESTROPIPATE
SALT/SOLVATE -> PARENT
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TRANSPORTER -> INHIBITOR
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Structure of POTASSIUM ESTRONE SULFATE
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Structure of ESTRONE SODIUM SULFATE
SALT/SOLVATE -> PARENT
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> SUBSTRATE
Vmax
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TRANSPORTER -> INHIBITOR
OATP-8
TRANSPORTER -> INHIBITOR
SODIUM/BILE ACID COTRANSPORTER
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Structure of ESTRADIOL
PARENT -> METABOLITE
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
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