ESTROPIPATE

First marketed in 1931

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttp://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://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 2637		7.0 nM [EC50]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412	Agonist 2637

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 426 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 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Prostate cancer 177 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Obesity 204 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 8307	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 8307	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 8307	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 651	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 1670	substrate 985		inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 383 P-gp 1491 UGT1A10 289 UGT1A3 421 UGT2A1 32 CYP1A1 344 CYP1A2 1013 CYP2B6 648 CYP2E1 633	P-gp 252

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1588	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A10 289	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	major
CYP1A2 1013	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	no
UGT1A3 421	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
UGT2A1 32	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
CYP1A1 344	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2B6 648	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2C9 985	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes
CYP2E1 633	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP3A5 383	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/9635876/	yes
P-gp 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes
CYP3A4 1670	substrate 3264 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 1603	inhibitor 1584 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
Reproducibility of plasma and urinary sex hormone levels in premenopausal women over a one-year period.	1999 Dec	10613337
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.	2000 Feb 11	10660625
Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases.	2000 Jan 7	10623578
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
Biological effects of hormone replacement therapy in relation to serum estradiol levels.	2001	11815726
Estrogen sulfamates: a new approach to oral estrogen therapy.	2001	11800168
Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women.	2001	11588903
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.	2001 Apr	11352550
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women.	2001 Apr	11294513
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.	2001 Apr 20	11306210
Postmenopausal endogenous oestrogens and risk of endometrial cancer: results of a prospective study.	2001 Apr 6	11286480
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).	2001 Apr 9	11294387
Prospective randomized study of effects of unopposed estrogen replacement therapy on markers of coagulation and inflammation in postmenopausal women.	2001 Aug	11502788
[Effects of oral administration of estrogen replacement therapy in surgical menopause].	2001 Dec	11883282
Comparison of estrogen and androgen levels after oral estrogen replacement therapy.	2001 Dec	11789085
The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase.	2001 Dec	11753757
Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.	2001 Feb	11159893
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.	2001 Feb	11398990
Plasma beta-endorphin levels in obese and non-obese patients with polycystic ovary disease.	2001 Feb	11293919
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	11200884
Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens.	2001 Jan	11231976
Effects of estrone sulfate alone or with medroxyprogesterone acetate on serum lipoprotein levels in postmenopausal women.	2001 Jan	11152917
Evolution of 17beta-HSD type 4, a multifunctional protein of beta-oxidation.	2001 Jan 22	11165031
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.	2001 Jan 22	11165029
Mechanisms of estradiol inactivation in primate endometrium.	2001 Jan 22	11165027
Beneficial effects of pravastatin in peri- and postmenopausal hyperlipidemic women: a 5-year study on serum lipid and sex hormone levels.	2001 Jan 31	11173182
Influence of endogenous androgens on carotid wall in postmenopausal women.	2001 Jan-Feb	11201514
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.	2001 Jul	11408524
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.	2001 Jul-Aug	11600235
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.	2001 Jun	11397849
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1.	2001 Jun 15	11389699
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.	2001 Mar	11355746
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents.	2001 Mar	11284326
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	11293581
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.	2001 May	11355334
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.	2001 May	11331656
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.	2001 May 1	11301044
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.	2001 May-Jun	11392373
Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women.	2001 Oct	11579354
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
Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.	2002 Aug	12175967
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.	2002 Jul 26	12011098
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.	2002 Mar 8	12005172
Interaction of human organic anion transporters with various cephalosporin antibiotics.	2002 Mar 8	11909604
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.	2002 May	12018985

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

ESTROPIPATE

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

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