Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H21O5S.Na |
Molecular Weight | 372.4129 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])CCC1=O)OS(=O)(=O)[O-].[Na+]
InChI
InChIKey=VUCAHVBMSFIGAI-ZFINNJDLSA-M
InChI=1S/C18H22O5S.Na/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
Molecular Formula | C18H21O5S |
Molecular Weight | 349.4231 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031https://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/ja00536a023Curator's Comment:: https://books.google.ru/books?id=Thtz7On_lhEC&pg=PA356&lpg=PA356&dq=DL-ESTRONE retrieved from The Hormones V1: Physiology, Chemistry and Applications
By Gregory Pincus, Thimann Kenneth Vivian Pincus Gregory, p.356
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031https://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/ja00536a023
Curator's Comment:: https://books.google.ru/books?id=Thtz7On_lhEC&pg=PA356&lpg=PA356&dq=DL-ESTRONE retrieved from The Hormones V1: Physiology, Chemistry and Applications
By Gregory Pincus, Thimann Kenneth Vivian Pincus Gregory, p.356
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. Estrogens enter the cells of responsive tissues (e.g. female organs, breasts, hypothalamus, pituitary) where they interact with estrogen receptors. Hormone-bound estrogen receptors dimerize, translocate to the nucleus of cells and bind to estrogen response elements (ERE) of genes. Binding to ERE alters the transcription rate of affected genes. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) release from the anterior pituitary. Estrone dl-Form is a derivative of estrone. As early as 1935 extensive research programs directed toward the total synthesis of the female
sex hormone estrone were well under way. These studies have since been continued with increasing interest in laboratories all over the world. In
1942 Bachmann, Kushner and Stevenson succeeded in synthesizing a stereoisomer of the hormone,''estrone a." Using essentially the same
synthetic scheme as Bachmann, et al., Anner and
Miescher were able to isolate additional stereoisomers including dl-estrone (Estrone, (+-)-Isomer) . Six of the eight possible racemic forms, estrone, a-f, have now
been reported. Dl-Estrone (Estrone, (+-)-Isomer) is less active than Estrone.
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: https://www.ncbi.nlm.nih.gov/pubmed/22469359http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsat
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 |
---|---|---|---|
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 |
---|---|---|
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice. | 2001 |
|
Trial protocol and sample result of a study comparing the Clearplan Easy Fertility Monitor with serum hormone and vaginal ultrasound measurements in the determination of ovulation. | 2001 |
|
Effects of oral and transdermal estrogen replacement therapy on markers of coagulation, fibrinolysis, inflammation and serum lipids and lipoproteins in postmenopausal women. | 2001 Apr |
|
Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin. | 2001 Apr |
|
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women. | 2001 Apr |
|
Measurement of urinary and fecal steroid metabolites during the ovarian cycle in captive and wild Japanese macaques, Macaca fuscata. | 2001 Apr |
|
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo. | 2001 Apr |
|
Do urinary estrogen metabolites reflect the differences in breast cancer risk between Singapore Chinese and United States African-American and white women? | 2001 Apr 15 |
|
Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3. | 2001 Apr 15 |
|
Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines. | 2001 Apr 20 |
|
Cholesterol sulfate: a new adhesive molecule for platelets. | 2001 Apr 24 |
|
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 |
|
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells. | 2001 Feb |
|
4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout. | 2001 Feb |
|
Dietary oleoyl-estrone delays the growth rate of young rats. | 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 |
|
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol. | 2001 Feb 28 |
|
Hormone contents in peripheral tissues after correct and off-label use of growth promoting hormones in cattle: effect of the implant preparations Filaplix-H, Raglo, Synovex-H and Synovex Plus. | 2001 Jan |
|
Bioequivalence and relative bioavailability of three estradiol and norethisterone acetate-containing hormone replacement therapy tablets. | 2001 Jan |
|
Mechanisms of estradiol inactivation in primate endometrium. | 2001 Jan 22 |
|
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3). | 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 |
|
Chalcones are potent inhibitors of aromatase and 17beta-hydroxysteroid dehydrogenase activities. | 2001 Jan 5 |
|
Characteristics of cystic breast disease with special regard to breast cancer development. | 2001 Jan-Feb |
|
Influence of endogenous androgens on carotid wall in postmenopausal women. | 2001 Jan-Feb |
|
Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female. | 2001 Jun |
|
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. | 2001 Jun |
|
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men. | 2001 Jun |
|
Fecal analysis of ovarian cycles in female black-handed spider monkeys (Ateles geoffroyi). | 2001 Jun |
|
[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers]. | 2001 Mar |
|
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study. | 2001 Mar |
|
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men. | 2001 Mar |
|
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents. | 2001 Mar |
|
Can variability in the hormonal status of elderly women assist in the decision to administer estrogens? | 2001 Mar |
|
Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease. | 2001 Mar |
|
Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes. | 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 |
|
Novel inhibitors of the enzyme estrone sulfatase (ES). | 2001 Mar 26 |
|
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides. | 2001 Mar-Apr |
|
Urinary excretion pattern of catecholestrogens in preovulatory LH surge during the 4-day estrous cycle of rats. | 2001 May |
|
In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide. | 2001 May |
|
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer. | 2001 May |
|
Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells. | 2001 May |
|
Pharmacologic, but not dietary, genistein supports endometriosis in a rat model. | 2001 May |
|
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism. | 2001 May 15 |
|
A polymorphism in CYP17 and endometrial cancer risk. | 2001 May 15 |
|
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction. | 2001 May 15 |
|
Serum hormones and the alcohol-breast cancer association in postmenopausal women. | 2001 May 2 |
Sample Use Guides
In Vivo Use Guide
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031
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
5 pellets 3 times a day until symptoms are relieved
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27169275
Study was designed to discover filovirus entry inhibitors in a drug library of commercial medicines. One thousand and six hundred drugs were screened using the ZEBOV-GP/HIV model, a pseudovirus formed by an HIV-core packed with the Zaire Ebola virus glycoprotein. Was identified 12 gonadal hormone drugs with inhibitory activities in ZEBOV-GP/HIV entry at final concentration of 10 μmol x L(-1). One of them with moderate activity was estrone IC50: 6.87 ± 0.03 μmol-L1
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 01:20:18 UTC 2021
by
admin
on
Sat Jun 26 01:20:18 UTC 2021
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Record UNII |
6K6FDA543A
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C2181
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6K6FDA543A
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438-67-5
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23667301
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DB00286
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C61942
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SUB01976MIG
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C017296
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207-120-4
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91428
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ACTIVE MOIETY |