Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H22O2 |
Molecular Weight | 270.3661 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(O)=CC=C34)[C@@H]1CCC2=O
InChI
InChIKey=DNXHEGUUPJUMQT-CBZIJGRNSA-N
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
Molecular Formula | C18H22O2 |
Molecular Weight | 270.3661 |
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.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 |
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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 |
---|---|---|
Biological effects of hormone replacement therapy in relation to serum estradiol levels. | 2001 |
|
Estrogen sulfamates: a new approach to oral estrogen therapy. | 2001 |
|
[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 |
|
Estrogen replacement therapy after breast cancer: a 12-year follow-up. | 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 |
|
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 |
|
The effects of PCB exposure and fish consumption on endogenous hormones. | 2001 Dec |
|
Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases. | 2001 Dec |
|
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 |
|
[Prevention and treatment of recurrent urinary system infection with estrogen cream in postmenopausal women]. | 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 |
|
The role of cytokines in regulating estrogen synthesis: implications for the etiology of breast cancer. | 2002 |
|
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES). | 2002 Apr |
|
Number of years since menopause: spontaneous bone loss is dependent but response to hormone replacement therapy is independent. | 2002 Apr |
|
Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta. | 2002 Apr |
|
Bone loss at the femoral neck in premenopausal white women: effects of weight change and sex-hormone levels. | 2002 Apr |
|
An evolutionarily ancient Oatp: insights into conserved functional domains of these proteins. | 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 |
|
Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies. | 2002 Apr 17 |
|
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 |
|
A randomized isoflavone intervention among premenopausal women. | 2002 Feb |
|
Influence of letrozole and anastrozole on total body aromatization and plasma estrogen levels in postmenopausal breast cancer patients evaluated in a randomized, cross-over study. | 2002 Feb 1 |
|
Transcellular transport of organic anions across a double-transfected Madin-Darby canine kidney II cell monolayer expressing both human organic anion-transporting polypeptide (OATP2/SLC21A6) and Multidrug resistance-associated protein 2 (MRP2/ABCC2). | 2002 Feb 22 |
|
Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer. | 2002 Jan |
|
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 |
|
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 |
|
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta. | 2002 Mar |
|
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 |
|
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 |
|
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2. | 2002 May |
Sample Use Guides
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 07:04:09 GMT 2025
by
admin
on
Wed Apr 02 07:04:09 GMT 2025
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Record UNII |
2DI9HA706A
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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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LOINC |
25403-7
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2258-2
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LIVERTOX |
376
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13739-8
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WHO-ATC |
G03CA07
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22663-9
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34297-2
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34299-8
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31177-9
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CFR |
21 CFR 862.1430
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LOINC |
27998-4
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2257-4
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6776-9
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35208-8
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2261-6
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G03CC04
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LOINC |
14160-6
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34298-0
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2260-8
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2262-4
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2259-0
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WHO-VATC |
QG03CA07
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CFR |
21 CFR 862.1280
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WHO-VATC |
QG03CC04
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Code System | Code | Type | Description | ||
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ESTRONE
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53-16-7
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2DI9HA706A
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CHEMBL1405
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2DI9HA706A
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C484
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Estrone (medication)
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m5033
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DB00655
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DTXSID4022367
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE LESS ACTIVE -> PARENT | |||
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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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METABOLITE -> PARENT |
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PARENT -> IMPURITY | |||
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PARENT -> IMPURITY | |||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
USP
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ACTIVE MOIETY |