U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O5S.C4H10N2
Molecular Weight 436.565
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTROPIPATE

SMILES

C1CNCCN1.[H][C@@]23CCC(=O)[C@@]2(C)CC[C@]4([H])C5=C(CC[C@@]34[H])C=C(OS(O)(=O)=O)C=C5

InChI

InChIKey=HZEQBCVBILBTEP-ZFINNJDLSA-N
InChI=1S/C18H22O5S.C4H10N2/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;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C4H10N2
Molecular Weight 86.1356
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H22O5S
Molecular Weight 350.429
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
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
Unknown

Approved Use

Unknown
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
Reproducibility of plasma and urinary sex hormone levels in premenopausal women over a one-year period.
1999 Dec
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
Biological effects of hormone replacement therapy in relation to serum estradiol levels.
2001
Estrogen sulfamates: a new approach to oral estrogen therapy.
2001
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution.
2001
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice.
2001
On call. My wife's doctor gave her Premarin for her cholesterol. I know it's a female hormone, but my cholesterol is also high, and I wonder if it could help me, too.
2001 Apr
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.
2001 Apr
Effects of testosterone precursor supplementation on intensive weight training.
2001 Apr
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1).
2001 Apr
Estrogen replacement therapy after breast cancer: a 12-year follow-up.
2001 Dec
The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase.
2001 Dec
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
Effect of estrogen on endothelial dysfunction in postmenopausal women with diabetes.
2001 Dec
By the way, doctor. I've been taking hormone replacement with Premarin and Provera for 12 years. Now that I'm 68 years old, I'd like to stop taking the hormones, but I don't know how. What is the best way to get off HRT?
2001 Feb
Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.
2001 Feb
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.
2001 Feb
Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro.
2001 Jan
Sleep in menopause: differential effects of two forms of hormone replacement therapy.
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
Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female.
2001 Jun
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men.
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
Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes.
2001 Mar
[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers].
2001 Mar
Daily oral oleoyl-estrone gavage induces a dose-dependent loss of fat in Wistar rats.
2001 Mar
Actions of the soy phytoestrogen genistein in models of human chronic disease: potential involvement of transforming growth factor beta.
2001 May
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.
2001 May
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
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 culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.
2001 May 1
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism.
2001 May 15
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women.
2001 May-Jun
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.
2001 May-Jun
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
Regulation of human apolipoprotein A-I gene expression by equine estrogens.
2001 Nov
Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women.
2001 Oct
Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C.
2001 Sep
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).
2002 Apr
Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies.
2002 Apr 17
Hormonal measurements in late pregnancy and parturition in dairy cows--possible tools to monitor foetal well being.
2002 Aug 15
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
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.
2002 Jun
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer.
2002 Mar
Estrogens affect endothelin-1 mRNA expression in LNCaP human prostate carcinoma cells.
2002 May
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
2002 May
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
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
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 Wed Jul 05 22:34:12 UTC 2023
Edited
by admin
on Wed Jul 05 22:34:12 UTC 2023
Record UNII
SVI38UY019
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTROPIPATE
MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
Estrone hydrogen sulfate compound with piperazine (1:1)
Common Name English
ESTROPIPATE [MART.]
Common Name English
ESTROPIPATE [ORANGE BOOK]
Common Name English
HARMOGEN
Brand Name English
PIPERAZINE ESTRONE SULPHATE
Common Name English
ESTROPIPATE [USP-RS]
Common Name English
OGEN
Brand Name English
ESTRONE HYDROGEN SULPHATE COMPOUND WITH PIPERAZINE (1:1)
Common Name English
NSC-758912
Code English
PIPERAZINE ESTRONE SULFATE
Common Name English
ESTROPIPATE [USP MONOGRAPH]
Common Name English
Estropipate [WHO-DD]
Common Name English
ESTRONE SULFATE PIPERAZINE SALT [MI]
Common Name English
ESTRONE SULFATE PIPERAZINE SALT
MI  
Common Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-(SULFOOXY)-, COMPD. WITH PIPERAZINE (1:1)
Systematic Name English
ESTROPIPATE [VANDF]
Common Name English
ORTHO-EST
Brand Name English
SULESTREX PIPERAZINE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C2181
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
LIVERTOX 377
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID3023005
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
EVMPD
SUB13724MIG
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
SMS_ID
100000078982
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
DRUG BANK
DB04574
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
MERCK INDEX
M5033
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1255500
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
CAS
7280-37-7
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
PUBCHEM
5284555
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
DAILYMED
SVI38UY019
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
230-696-3
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
NCI_THESAURUS
C47521
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
NSC
758912
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
WIKIPEDIA
Estropipate
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
FDA UNII
SVI38UY019
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL494753
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY
RXCUI
33747
Created by admin on Wed Jul 05 22:34:12 UTC 2023 , Edited by admin on Wed Jul 05 22:34:12 UTC 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY