Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H21O5S.Na |
Molecular Weight | 372.411 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS([O-])(=O)=O)=C4)[C@@H]1CCC2=O
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 | Na |
Molecular Weight | 22.98976928 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H21O5S |
Molecular Weight | 349.421 |
Charge | -1 |
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.pdfhttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031http://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://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-424c58303031http://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 |
|||
Diagnostic | Unknown Approved UseUnknown |
|||
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 |
---|---|---|
Estrogen sulfamates: a new approach to oral estrogen therapy. | 2001 |
|
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution. | 2001 |
|
Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women. | 2001 |
|
Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3. | 2001 Apr 15 |
|
Structural and functional consequences of inactivation of human glutathione S-transferase P1-1 mediated by the catechol metabolite of equine estrogens, 4-hydroxyequilenin. | 2001 Apr 17 |
|
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy. | 2001 Apr 20 |
|
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 |
|
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 |
|
By the way, Doctor. Whenever I read about the effects of hormone replacement therapy (HRT), the researchers always seem to use 0.625 mg of Premarin. I'm taking 1 mg of Estrace daily. How does this compare to the standard dose of Premarin? | 2001 Dec |
|
Paradoxical effect of estradiol: it can block its own bioformation in human breast cancer cells. | 2001 Jul |
|
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 |
|
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group. | 2001 Jul-Aug |
|
Serum lipid profile improved by ultra-low doses of 17 beta-estradiol in elderly women. | 2001 Jun |
|
Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys. | 2001 Jun 15 |
|
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures. | 2001 May 1 |
|
Arginine 454 and lysine 370 are essential for the anion specificity of the organic anion transporter, rOAT3. | 2001 May 8 |
|
Effect of transforming growth factor-beta1, insulin-like growth factor-I and insulin-like growth factor-II on cell growth and oestrogen metabolism in human breast cancer cell lines. | 2001 Nov |
|
Endocrinology of gynaecomastia. | 2001 Nov |
|
Regulation of human apolipoprotein A-I gene expression by equine estrogens. | 2001 Nov |
|
Micronized progesterone regulation of the endometrial glandular cycling pool. | 2001 Oct |
|
Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women. | 2001 Oct |
|
Tibolone: a compound with tissue specific inhibitory effects on sulfatase. | 2001 Oct 25 |
|
Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C. | 2001 Sep |
|
Hormone replacement therapy for cognitive function in postmenopausal women. | 2002 |
|
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe. | 2002 |
|
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 |
|
Hormonal measurements in late pregnancy and parturition in dairy cows--possible tools to monitor foetal well being. | 2002 Aug 15 |
|
Functional characterization of the mouse organic-anion-transporting polypeptide 2. | 2002 Aug 19 |
|
Endocrine changes in late bovine pregnancy with special emphasis on fetal well-being. | 2002 Jul |
|
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation. | 2002 Jul |
|
Mammary secretion of oestrogens in the cow. | 2002 Jul |
|
Does place of birth influence endogenous hormone levels in Asian-American women? | 2002 Jul 1 |
|
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition. | 2002 Jul 16 |
|
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice. | 2002 Jul 26 |
|
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance. | 2002 Jun |
|
Alveolar and postcranial bone density in postmenopausal women receiving hormone/estrogen replacement therapy: a randomized, double-blind, placebo-controlled trial. | 2002 Jun 24 |
|
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. | 2002 Mar 8 |
|
The IGF-system in healthy pre- and postmenopausal women: relations to demographic variables and sex-steroids. | 2002 May |
|
Specific radioimmunoassay of estrone sulfate. Application to measurement in male plasma. | 2002 May |
|
Estrogens affect endothelin-1 mRNA expression in LNCaP human prostate carcinoma cells. | 2002 May |
|
Effects of lactation length and an exogenous progesterone and estradiol-17beta regimen during embryo attachment on endogenous steroid concentrations and embryo survival in sows. | 2002 May |
|
The choice of hormone replacement therapy or statin therapy in the treatment of hyperlipidemic postmenopausal women. | 2002 May |
|
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory. | 2002 May |
|
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women. | 2002 May |
|
Association of CYP1B1 polymorphisms and breast cancer risk. | 2002 May |
Sample Use Guides
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:32:07 GMT 2025
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on
Mon Mar 31 18:32:07 GMT 2025
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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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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |