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

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

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
Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases.
2000 Jan 7
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
Biological effects of hormone replacement therapy in relation to serum estradiol levels.
2001
Estrogen sulfamates: a new approach to oral estrogen therapy.
2001
Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women.
2001
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
2001 Apr
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women.
2001 Apr
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.
2001 Apr 20
Postmenopausal endogenous oestrogens and risk of endometrial cancer: results of a prospective study.
2001 Apr 6
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).
2001 Apr 9
Prospective randomized study of effects of unopposed estrogen replacement therapy on markers of coagulation and inflammation in postmenopausal women.
2001 Aug
[Effects of oral administration of estrogen replacement therapy in surgical menopause].
2001 Dec
Comparison of estrogen and androgen levels after oral estrogen replacement therapy.
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
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
Plasma beta-endorphin levels in obese and non-obese patients with polycystic ovary disease.
2001 Feb
Synthesis and biological evaluation of two new radiolabelled estrogens: [125I](E)-3-methoxy-17alpha-iodovinylestra-1,3,5(10),6-tetraen-17beta-ol and.
2001 Feb
Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens.
2001 Jan
Effects of estrone sulfate alone or with medroxyprogesterone acetate on serum lipoprotein levels in postmenopausal women.
2001 Jan
Evolution of 17beta-HSD type 4, a multifunctional protein of beta-oxidation.
2001 Jan 22
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.
2001 Jan 22
Mechanisms of estradiol inactivation in primate endometrium.
2001 Jan 22
Beneficial effects of pravastatin in peri- and postmenopausal hyperlipidemic women: a 5-year study on serum lipid and sex hormone levels.
2001 Jan 31
Influence of endogenous androgens on carotid wall in postmenopausal women.
2001 Jan-Feb
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.
2001 Jul
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.
2001 Jul-Aug
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.
2001 Jun
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1.
2001 Jun 15
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.
2001 Mar
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents.
2001 Mar
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
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.
2001 May
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.
2001 May
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.
2001 May 1
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.
2001 May-Jun
Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women.
2001 Oct
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).
2002 Apr
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
Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.
2002 Aug
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.
2002 Jul 26
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.
2002 Mar 8
Interaction of human organic anion transporters with various cephalosporin antibiotics.
2002 Mar 8
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.
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
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 16 15:58:28 UTC 2022
Edited
by admin
on Fri Dec 16 15:58:28 UTC 2022
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 Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
LIVERTOX 377
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
Code System Code Type Description
EPA CompTox
DTXSID3023005
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
EVMPD
SUB13724MIG
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
DRUG BANK
DB04574
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
MERCK INDEX
M5033
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY Merck Index
RS_ITEM_NUM
1255500
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
CAS
7280-37-7
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
PUBCHEM
5284555
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
DAILYMED
SVI38UY019
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
ECHA (EC/EINECS)
230-696-3
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
NCI_THESAURUS
C47521
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
NSC
758912
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
WIKIPEDIA
Estropipate
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
FDA UNII
SVI38UY019
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
ChEMBL
CHEMBL494753
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY
RXCUI
33747
Created by admin on Fri Dec 16 15:58:28 UTC 2022 , Edited by admin on Fri Dec 16 15:58:28 UTC 2022
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY