Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H21O5S.K |
Molecular Weight | 388.52 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[K+].[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OS([O-])(=O)=O)C=C4
InChI
InChIKey=CUQHOFAEIPGLBH-ZFINNJDLSA-M
InChI=1S/C18H22O5S.K/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);/q;+1/p-1/t14-,15-,16+,18+;/m1./s1
DescriptionSources: http://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://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031Curator'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
Sources: http://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://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttps://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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11105986
Curator's Comment: Estrone sulfate crossed the blood brain barrier in rats.
Originator
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsathttps://www.ncbi.nlm.nih.gov/pubmed/22469359
Curator's Comment: Estrone is one of the hormones responsible for sexual development and function in females.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL206 |
7.0 nM [EC50] | ||
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Primary | Estragyn Approved UseEstragyn 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. |
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Primary | Estragyn Approved UseEstragyn 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. |
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Primary | THEELIN Approved UseFor management of Menopausal and postmenopausal disorders |
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Palliative | Unknown Approved UseUnknown |
Cmax
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 |
T1/2
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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
no | ||||
weak | ||||
weak | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
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 |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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Reproducibility of plasma and urinary sex hormone levels in premenopausal women over a one-year period. | 1999 Dec |
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Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. | 1999 May 7 |
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Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. | 2000 Feb 11 |
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Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells. | 2000 Jan-Feb |
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Biological effects of hormone replacement therapy in relation to serum estradiol levels. | 2001 |
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Estrogen sulfamates: a new approach to oral estrogen therapy. | 2001 |
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Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women. | 2001 |
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Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice. | 2001 |
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Futile cycling of estrone sulfate and estrone in the recirculating perfused rat liver preparation. | 2001 Apr |
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Prospective randomized study of effects of unopposed estrogen replacement therapy on markers of coagulation and inflammation in postmenopausal women. | 2001 Aug |
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Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome. | 2001 Aug 9 |
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[Effects of oral administration of estrogen replacement therapy in surgical menopause]. | 2001 Dec |
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Comparison of estrogen and androgen levels after oral estrogen replacement therapy. | 2001 Dec |
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Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases. | 2001 Dec |
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Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. | 2001 Feb |
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Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens. | 2001 Jan |
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Effects of estrone sulfate alone or with medroxyprogesterone acetate on serum lipoprotein levels in postmenopausal women. | 2001 Jan |
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Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins. | 2001 Jan |
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Sleep in menopause: differential effects of two forms of hormone replacement therapy. | 2001 Jan-Feb |
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Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group. | 2001 Jul-Aug |
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Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. | 2001 Jun |
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Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female. | 2001 Jun |
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Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys. | 2001 Jun 15 |
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[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers]. | 2001 Mar |
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Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney. | 2001 Mar 19 |
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Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1. | 2001 Mar 2 |
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Actions of the soy phytoestrogen genistein in models of human chronic disease: potential involvement of transforming growth factor beta. | 2001 May |
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Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures. | 2001 May 1 |
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Serum hormones and the alcohol-breast cancer association in postmenopausal women. | 2001 May 2 |
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Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women. | 2001 May-Jun |
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Endocrinology of gynaecomastia. | 2001 Nov |
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Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women. | 2001 Oct |
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Polymorphisms in OATP-C: identification of multiple allelic variants associated with altered transport activity among European- and African-Americans. | 2001 Sep 21 |
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Hormone replacement therapy for cognitive function in postmenopausal women. | 2002 |
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Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta. | 2002 Apr |
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Hormonal measurements in late pregnancy and parturition in dairy cows--possible tools to monitor foetal well being. | 2002 Aug 15 |
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Transcellular transport of organic anions across a double-transfected Madin-Darby canine kidney II cell monolayer expressing both human organic anion-transporting polypeptide (OATP2/SLC21A6) and Multidrug resistance-associated protein 2 (MRP2/ABCC2). | 2002 Feb 22 |
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Endocrine changes in late bovine pregnancy with special emphasis on fetal well-being. | 2002 Jul |
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The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation. | 2002 Jul |
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Mammary secretion of oestrogens in the cow. | 2002 Jul |
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Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice. | 2002 Jul 26 |
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Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors. | 2002 Mar |
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Characterization of iodothyronine sulfatase activities in human and rat liver and placenta. | 2002 Mar |
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Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. | 2002 Mar 8 |
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The IGF-system in healthy pre- and postmenopausal women: relations to demographic variables and sex-steroids. | 2002 May |
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Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory. | 2002 May |
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Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women. | 2002 May |
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A new route to (+)-estrone using a bicyclo[3.2.1]octane chiral building block. | 2003 Jan |
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Formal enantioselective synthesis of (+)-estrone. | 2007 Mar 15 |
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Catalytic asymmetric Torgov cyclization: a concise total synthesis of (+)-estrone. | 2014 Aug 11 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.rxwiki.com/estrone
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11039493
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.
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Code | English |
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C017296
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DBSALT002493
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23674502
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C354LET0O4
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1240-04-6
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214-985-1
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18054
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD