Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H24O3 |
Molecular Weight | 288.382 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])C[C@]([H])([C@]1([H])O)O)O
InChI
InChIKey=PROQIPRRNZUXQM-ZXXIGWHRSA-N
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
Molecular Formula | C18H24O3 |
Molecular Weight | 288.382 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugs.com/pro/estradiol.htmlCurator's Comment:: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02906111 | https://www.ncbi.nlm.nih.gov/pubmed/27838536 | https://clinicaltrials.gov/ct2/show/NCT02419729 | https://www.ncbi.nlm.nih.gov/pubmed/26786399 |
Sources: https://www.drugs.com/pro/estradiol.html
Curator's Comment:: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02906111 | https://www.ncbi.nlm.nih.gov/pubmed/27838536 | https://clinicaltrials.gov/ct2/show/NCT02419729 | https://www.ncbi.nlm.nih.gov/pubmed/26786399 |
Estriol (E3), also spelled oestriol, is a steroid, a weak agonist of the estrogen receptors ERα and ERβ., and a minor female sex hormone. According to in vitro study, the relative binding affinity (RBA) of estriol for the human ERα and ERβ was 11.3% and 17.6% of that estradiol, respectively, and the relative transactivational capacity of estrone at the ERα and ERβ was 10.6% and 16.6% of that of estradiol, respectively. Estriol is marketed widely in Europe and elsewhere throughout the world under the brand names Ovestin, Ortho-Gynest, and a variety of others. It is available in oral tablet, vaginal cream, and vaginal suppository form, and is used in menopausal hormone therapy for the treatment of menopausal symptoms. Estriol is also available in some countries as estriol succinate (brand name Synapause), a dosage-equivalent ester prodrug of estriol. Estriol and estriol succinate are not approved for use in the United States and Canada, although they have been produced and sold by compounding pharmacies in North America for use as a component of bioidentical hormone therapy. Estriol can be measured in maternal blood or urine and can be used as a marker of fetal health and well-being. If levels of unconjugated estriol (uE3 or free estriol) are abnormally low in a pregnant woman, this may indicate chromosomal or congenital anomalies like Down syndrome or Edward's syndrome. It is included as part of the triple test and quadruple test for antenatal screening for fetal anomalies.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9357533 |
|||
Target ID: CHEMBL3305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18330978 |
234.42 nM [Kd] | ||
Target ID: CHEMBL2421 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15139751 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Ovestin Approved UseUnknown |
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Primary | Ovestin Approved UseUnknown |
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Primary | Ovestin Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Plasma levels and excretion of estrogens in urine in chronic lever disease. | 1975 Jul |
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[Hormone replacement therapy in women with arterial hypertension in peri- and postmenopause: hemodynamic effects]. | 2001 |
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Multiple marker second trimester serum screening for pre-eclampsia. | 2001 |
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Determination of estradiol metabolites in human liver microsome by high performance liquid chromatography-electrochemistry detector. | 2001 Apr |
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Effect of oral estriol on urogenital symptoms, vaginal cytology, and plasma hormone level in postmenopausal women. | 2001 Apr |
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Triple-test screening in in vitro fertilization pregnancies. | 2001 Apr |
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Preterm birth risk assessment. | 2001 Aug |
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Second trimester maternal serum analytes in triploid pregnancies: correlation with phenotype and sex chromosome complement. | 2001 Aug |
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Maternal serum screening for fetal trisomy 18: benefits of patient-specific risk protocol. | 2001 Aug |
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Identification of 16alpha,19-dihydroxyandrostenedione in the serum of pregnant women by gas chromatography-mass spectrometry. | 2001 Aug |
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Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells. | 2001 Aug 1 |
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Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome. | 2001 Aug 9 |
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Sequential first and second trimester screening tests: correlation of the markers' levels in normal versus Down syndrome affected pregnancies. | 2001 Dec |
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Plasma prolactin/oestradiol ratio at 38 weeks gestation predicts the duration of lactational amenorrhoea. | 2001 Dec |
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Use of solid-phase extraction in various of its modalities for sample preparation in the determination of estrogens and progestogens in sediment and water. | 2001 Dec 14 |
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Removal of endocrine-disrupting chemicals in activated sludge treatment works. | 2001 Dec 15 |
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Treatment of bitches with acquired urinary incontinence with oestriol. | 2001 Dec 22-29 |
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Oestriol and oestradiol increase cell to cell communication and connexin43 protein expression in human myometrium. | 2001 Jul |
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An immunoassay for small analytes with theoretical detection limits. | 2001 Jul 15 |
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Maternal serum screening for Down's syndrome, open neural tube defects and trisomy 18. | 2001 Jun |
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Sex hormones in experimental autoimmune encephalomyelitis: implications for multiple sclerosis. | 2001 Jun |
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Plasma progesterone, dehydroepiandrosterone sulfate and estriol levels during labor induction with a sustained-release prostaglandin E2 vaginal insert. | 2001 Jun |
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False positive serum biochemical screening and subsequent fetal loss in women less than 35 years of age. | 2001 Jun |
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Facilitated tissue expansion with topical estriol. | 2001 Jun |
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Determination of estrogens in river water by gas chromatography-negative-ion chemical-ionization mass spectrometry. | 2001 Jun 15 |
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Estriol improves membrane fluidity of erythrocytes by the nitric oxide-dependent mechanism: an electron paramagnetic resonance study. | 2001 May |
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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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Pregnancy outcome and long term prognosis in 868 children born after second trimester amniocentesis for maternal serum positive triple test screening and normal prenatal karyotype. | 2001 May |
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Effect of incorrect gestational dating on Down's syndrome and neural tube risk assessment. | 2001 May |
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[Indications of fetal chromosome abnormalities in 1st trimester ultrasound]. | 2001 May 3 |
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Lens culinaris agglutinin-reactive alpha-fetoprotein, an alternative variant to alpha-fetoprotein in prenatal screening for Down's syndrome. | 2001 Nov |
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[Influence of hormonal replacement therapy on bacterial vaginosis in the group of peri- and postmenopausal women]. | 2001 Oct |
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[Health Council of Netherlands recommendation 'Serum screening for risk assessment of Down syndrome for all women' poorly supported]. | 2001 Oct 20 |
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[Cross-over comparison of the pharmacokinetics of estradiol during hormone replacement therapy with estradiol valerate or micronized estradiol]. | 2001 Sep |
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Inaccurate estimation of risk in second trimester serum screening for Down syndrome among women who have already had first trimester screening. | 2001 Sep |
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Mammographic density changes during different postmenopausal hormone replacement therapies. | 2001 Sep |
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Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. | 2001 Sep 14 |
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Short term oral estriol treatment restores normal premenopausal vaginal flora to elderly women. | 2001 Sep 28 |
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Accuracy of expected risk of Down syndrome using the second-trimester triple test. | 2002 |
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Estradiol valerate/dienogest. | 2002 |
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Use of low potency estrogens does not reduce the risk of hip fracture. | 2002 Apr |
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Reduced 11beta-hydroxysteroid dehydrogenase type 2 activity is associated with decreased birth weight centile in pregnancies complicated by asthma. | 2002 Apr |
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Steroid hormone levels during pregnancy and incidence of maternal breast cancer. | 2002 Apr |
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Serial first- and second-trimester Down's syndrome screening tests among IVF-versus naturally-conceived singletons. | 2002 Apr |
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A negative second trimester triple test and absence of specific ultrasonographic markers may decrease the need for genetic amniocentesis in advanced maternal age by 60%. | 2002 Jan |
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Plasma corticotropin-releasing hormone and unconjugated estriol in human pregnancy: gestational patterns and ability to predict preterm delivery. | 2002 Jan |
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Effect of various oestrogens on cell injury and alteration of apical transporters induced by tert-butyl hydroperoxide in renal proximal tubule cells. | 2002 Jan-Feb |
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Pregnancy outcomes of women with positive serum screening results for Down syndrome and trisomy 18. | 2002 Mar |
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Correlation of ultrasound findings and biochemical markers in the second trimester of pregnancy in fetuses with trisomy 21. | 2002 Mar |
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Topical estrogens combined with argon plasma coagulation in the management of epistaxis in hereditary hemorrhagic telangiectasia. | 2002 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02906111
1 g/daily of the vaginal gel containing 50 μg of estriol (0.005%) for 3 weeks and then twice weekly for 9 weeks, for a complete cycle of treatment of 12 weeks
Route of Administration:
Vaginal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25496649
TNBC cell lines HCC1806, HCC70 and MDA-MB-231 were used for activity evaluation. For stimulation of TNBC cells to analyze signal transduction of GPR30, 4×106 cells were plated in culture medium into 25 cm2 -culture flasks. After attachment, cells were serum starved for 24 hours to synchronize the 17β- estradiol-starved cells in G0-phase. Serum starved cells were treated for 30 minutes either with 10^−4 M estriol or solvent (0.1% ethanol) and subsequently stimulated with 10^−8 M 17β-estradiol in 0.1% ethanol for 10 min or 20 minutes. Cells were harvested and cell pellets lysed in 100 μl Cell lytic M (Sigma, Deisendorf, Germany), supplemented with protease-inhibitor (Sigma, Deisendorf, Germany) and phosphatase-inhibitor (Sigma, Deisendorf, Germany).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:15:11 UTC 2021
by
admin
on
Fri Jun 25 21:15:11 UTC 2021
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Record UNII |
FB33469R8E
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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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WHO-ATC |
G03CC06
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21264-7
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LOINC |
30510-2
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LOINC |
43802-8
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15064-9
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20466-9
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2249-1
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LOINC |
14716-5
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WHO-ATC |
G03CA04
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LOINC |
2251-7
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EMA VETERINARY ASSESSMENT REPORTS |
INCURIN [AUTHORIZED]
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CFR |
21 CFR 862.1265
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LOINC |
2250-9
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LOINC |
27259-1
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LOINC |
16838-5
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LIVERTOX |
374
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LOINC |
32353-5
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LOINC |
2248-3
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LOINC |
14718-1
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WHO-VATC |
QG03CA04
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LOINC |
27225-2
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LOINC |
34293-1
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LOINC |
13737-2
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LOINC |
34292-3
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WHO-VATC |
QG03CC06
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LOINC |
2252-5
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LOINC |
21265-4
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14717-3
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LOINC |
44004-0
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CFR |
21 CFR 520.852
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LOINC |
2253-3
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FB33469R8E
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50-27-1
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3187
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CHEMBL193482
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50-27-1
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3590
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C80154
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4094
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DB04573
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5756
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D004964
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SUB01971MIG
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M5032
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200-022-2
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Estriol
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2821
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1254508
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PRIMARY | USP-RS |
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PRODRUG -> METABOLITE ACTIVE |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |