Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H22O5S |
Molecular Weight | 350.429 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[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=JKKFKPJIXZFSSB-CBZIJGRNSA-N
InChI=1S/C18H22O5S/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)/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 |
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. |
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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 |
---|---|---|
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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Biological effects of hormone replacement therapy in relation to serum estradiol levels. | 2001 |
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Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution. | 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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Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo. | 2001 Apr |
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Effects of testosterone precursor supplementation on intensive weight training. | 2001 Apr |
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Aromatase inhibition reduces specifically one display of the ring dove courtship behavior. | 2001 Apr |
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Oestrogens and oestrogenic activity in raw and treated water in Severn Trent Water. | 2001 Apr |
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Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines. | 2001 Apr 20 |
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Postmenopausal endogenous oestrogens and risk of endometrial cancer: results of a prospective study. | 2001 Apr 6 |
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Estrogen replacement therapy after breast cancer: a 12-year follow-up. | 2001 Dec |
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4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout. | 2001 Feb |
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Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol. | 2001 Feb 28 |
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Evolution of 17beta-HSD type 4, a multifunctional protein of beta-oxidation. | 2001 Jan 22 |
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Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3). | 2001 Jan 22 |
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Non-steroidal and steroidal sulfamates: new drugs for cancer therapy. | 2001 Jan 22 |
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Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells. | 2001 Jan 9 |
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Early postnatal plasma concentrations of testicular steroid hormones, pubertal development, and carcass leanness as potential indicators of boar taint in market weight intact male pigs. | 2001 Jul |
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Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver. | 2001 Jul |
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The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men. | 2001 Jun |
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Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy. | 2001 Jun |
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Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys. | 2001 Jun 15 |
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Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study. | 2001 Mar |
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Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents. | 2001 Mar |
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Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease. | 2001 Mar |
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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 |
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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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Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
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Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens. | 2001 May |
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2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells. | 2001 May |
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Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction. | 2001 May 15 |
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Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development. | 2001 May-Jun |
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Regulation of human apolipoprotein A-I gene expression by equine estrogens. | 2001 Nov |
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Micronized progesterone regulation of the endometrial glandular cycling pool. | 2001 Oct |
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[Prevention and treatment of recurrent urinary system infection with estrogen cream in postmenopausal women]. | 2001 Sep |
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Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C. | 2001 Sep |
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Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES). | 2002 Apr |
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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 |
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Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast. | 2002 Aug |
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Functional characterization of the mouse organic-anion-transporting polypeptide 2. | 2002 Aug 19 |
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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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Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition. | 2002 Jul 16 |
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A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance. | 2002 Jun |
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Alveolar and postcranial bone density in postmenopausal women receiving hormone/estrogen replacement therapy: a randomized, double-blind, placebo-controlled trial. | 2002 Jun 24 |
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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
Sat Dec 17 10:38:11 UTC 2022
by
admin
on
Sat Dec 17 10:38:11 UTC 2022
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Record UNII |
QTL48N278K
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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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LOINC |
15355-1
Created by
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Code System | Code | Type | Description | ||
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Estrone sulfate (medication)
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PRIMARY | |||
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C017296
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PRIMARY | |||
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C1091
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PRIMARY | |||
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ESTRONE SULFATE
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207-575-9
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QTL48N278K
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4749
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481-97-0
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DB04574
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M5033
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PRIMARY | Merck Index | ||
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17474
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SUB32459
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3001028
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DTXSID50891501
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4857
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TRANSPORTER -> SUBSTRATE |
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PARENT -> METABOLITE |
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
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