Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H22O5S |
Molecular Weight | 350.4311 |
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
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 | 350.4311 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|
Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells. | 2000 Jan-Feb |
|
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene. | 2000 Nov |
|
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice. | 2001 |
|
Home monitoring with the ClearPlan Easy Fertility Monitor for fertility awareness. | 2001 |
|
Effects of testosterone precursor supplementation on intensive weight training. | 2001 Apr |
|
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1). | 2001 Apr |
|
Effects of oral and transdermal estrogen replacement therapy on markers of coagulation, fibrinolysis, inflammation and serum lipids and lipoproteins in postmenopausal women. | 2001 Apr |
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Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women. | 2001 Apr |
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Futile cycling of estrone sulfate and estrone in the recirculating perfused rat liver preparation. | 2001 Apr |
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Estrogen and androgen influence hypothalamic AVP and CRF concentrations in fetal and adult sheep. | 2001 Apr 2 |
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Comparison of estrogen and androgen levels after oral estrogen replacement therapy. | 2001 Dec |
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The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase. | 2001 Dec |
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The effects of PCB exposure and fish consumption on endogenous hormones. | 2001 Dec |
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Effect of estrogen on endothelial dysfunction in postmenopausal women with diabetes. | 2001 Dec |
|
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells. | 2001 Feb |
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Periovulatory changes in catfish ovarian oestradiol-17beta, oestrogen-2-hydroxylase and catechol-O-methyltransferase during GnRH analogue-induced ovulation and in vitro induction of oocyte maturation by catecholoestrogens. | 2001 Feb |
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Differential in vitro suppressive effects of steroids on leukocyte phagocytosis in two teleosts, tilapia and common carp. | 2001 Feb |
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Effect of GnRH immunisation on hormonal levels, sexual behaviour, semen quality and testicular morphology in mature stallions. | 2001 Jan |
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Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults. | 2001 Jan |
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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 |
|
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase. | 2001 Jan 22 |
|
Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung. | 2001 Jan 22 |
|
The selective estrogen enzyme modulator (SEEM) in breast cancer. | 2001 Jan-Mar |
|
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver. | 2001 Jul |
|
Menopausal experiences and bone density of Mayan women in Yucatan, Mexico. | 2001 Jul-Aug |
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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 |
|
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. | 2001 Jun |
|
Association of genetic polymorphisms in UGT1A1 with breast cancer and plasma hormone levels. | 2001 Jun |
|
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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Serum levels of C-reactive protein are associated with obesity, weight gain, and hormone replacement therapy in healthy postmenopausal women. | 2001 Jun 1 |
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[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers]. | 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 |
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Urinary excretion pattern of catecholestrogens in preovulatory LH surge during the 4-day estrous cycle of rats. | 2001 May |
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Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. | 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 |
|
A polymorphism in CYP17 and endometrial cancer risk. | 2001 May 15 |
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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 |
|
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women. | 2001 May-Jun |
|
Tibolone: a compound with tissue specific inhibitory effects on sulfatase. | 2001 Oct 25 |
|
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe. | 2002 |
|
Bone loss at the femoral neck in premenopausal white women: effects of weight change and sex-hormone levels. | 2002 Apr |
|
Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies. | 2002 Apr 17 |
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Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast. | 2002 Aug |
|
Does place of birth influence endogenous hormone levels in Asian-American women? | 2002 Jul 1 |
|
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance. | 2002 Jun |
|
Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors. | 2002 Mar |
|
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer. | 2002 Mar |
|
Interaction of human organic anion transporters with various cephalosporin antibiotics. | 2002 Mar 8 |
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 10:22:59 UTC 2021
by
admin
on
Sat Jun 26 10:22:59 UTC 2021
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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
Created by
admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
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LOINC |
15355-1
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admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
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C017296
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C1091
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ESTRONE SULFATE
Created by
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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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SUB32459
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3001028
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4857
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Vmax
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TRANSPORTER -> SUBSTRATE |
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TRANSPORTER -> SUBSTRATE |
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Vmax
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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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