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
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
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 |
DescriptionSources: 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-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: 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
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 |
---|---|---|---|
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 |
---|---|---|---|---|
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. |
|||
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. |
|||
Primary | THEELIN Approved UseFor management of Menopausal and postmenopausal disorders |
|||
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 |
---|---|---|
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 |
---|---|---|
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 |
Sample Use Guides
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 15:58:28 UTC 2022
by
admin
on
Fri Dec 16 15:58:28 UTC 2022
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Record UNII |
SVI38UY019
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C2181
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LIVERTOX |
377
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DTXSID3023005
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SUB13724MIG
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DB04574
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M5033
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1255500
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7280-37-7
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5284555
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SVI38UY019
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230-696-3
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C47521
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758912
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Estropipate
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SVI38UY019
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CHEMBL494753
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33747
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |