Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H24O3 |
Molecular Weight | 288.3814 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4
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
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 |
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Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9357533 |
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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 |
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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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Biochemical markers for preterm labor and birth: what is their role in the care of pregnant women? | 1999 Mar-Apr |
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[Hormone replacement therapy in women with arterial hypertension in peri- and postmenopause: hemodynamic effects]. | 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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First-trimester increased nuchal translucency and fetal hypokinesia associated with Zellweger syndrome. | 2001 Apr |
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Comparison of triple serum screening and pregnancy outcome in oocyte donation versus IVF 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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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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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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[Trisomy 21 screening: value of ultrasound and serum markers in a combined approach]. | 2001 Feb |
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Low-dose estrogen therapy ameliorates experimental autoimmune encephalomyelitis in two different inbred mouse strains. | 2001 Feb 1 |
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Evaluation of effect of analytical imprecision in maternal serum screening for Down's syndrome. | 2001 Jan |
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Repeat testing in antenatal screening for Down syndrome using dimeric inhibin-A in combination with other maternal serum markers. | 2001 Jan |
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Estimates for the sensitivity and false-positive rates for second trimester serum screening for Down syndrome and trisomy 18 with adjustment for cross-identification and double-positive results. | 2001 Jan |
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[Hormone therapy in climacteric. Different effects of estrogen and gestagen on the risk of breast and endometrial cancer]. | 2001 Jan 31 |
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Hormone replacement therapy after invasive ovarian serous cystadenocarcinoma treatment: the effect on survival. | 2001 Jan-Feb |
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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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Mammographic breast density during hormone replacement therapy: effects of continuous combination, unopposed transdermal and low-potency estrogen regimens. | 2001 Mar |
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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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Gas chromatography-mass spectrometric determination of activity of human placental aromatase using 16alpha-hydroxyandrostenedione as a substrate. | 2001 May |
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A placebo-controlled trial of long-term oral combined continuous hormone replacement therapy in postmenopausal women: effects on arterial compliance and endothelial function. | 2001 Nov |
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Identification of negative and positive estrogen response elements in human GnRH upstream promoter in the placental JEG-3 cells. | 2001 Nov 26 |
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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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Short term oral estriol treatment restores normal premenopausal vaginal flora to elderly women. | 2001 Sep 28 |
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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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Plasma corticotropin-releasing hormone and unconjugated estriol in human pregnancy: gestational patterns and ability to predict preterm delivery. | 2002 Jan |
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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).
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NCI_THESAURUS |
C2181
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G03CC06
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21264-7
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30510-2
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2249-1
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14716-5
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G03CA04
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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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2250-9
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16838-5
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LIVERTOX |
374
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32353-5
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2248-3
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14718-1
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WHO-VATC |
QG03CA04
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27225-2
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34293-1
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13737-2
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34292-3
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QG03CC06
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2252-5
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14717-3
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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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DTXSID9022366
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1254508
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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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DB04573
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5756
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Estriol (medication)
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100000092668
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D004964
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M5032
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FB33469R8E
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200-022-2
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27974
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Estriol
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2821
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)