U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ESTRIOL

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

HIDE SMILES / InChI

Description
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.

Originator

Sources: Journal of Biological Chemistry (1931), 91, 655-65.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ovestin

Approved Use

Unknown
Primary
Ovestin

Approved Use

Unknown
Primary
Ovestin

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Plasma levels and excretion of estrogens in urine in chronic lever disease.
1975 Jul
[Hormone replacement therapy in women with arterial hypertension in peri- and postmenopause: hemodynamic effects].
2001
Multiple marker second trimester serum screening for pre-eclampsia.
2001
Determination of estradiol metabolites in human liver microsome by high performance liquid chromatography-electrochemistry detector.
2001 Apr
Effect of oral estriol on urogenital symptoms, vaginal cytology, and plasma hormone level in postmenopausal women.
2001 Apr
Triple-test screening in in vitro fertilization pregnancies.
2001 Apr
Preterm birth risk assessment.
2001 Aug
Second trimester maternal serum analytes in triploid pregnancies: correlation with phenotype and sex chromosome complement.
2001 Aug
Maternal serum screening for fetal trisomy 18: benefits of patient-specific risk protocol.
2001 Aug
Identification of 16alpha,19-dihydroxyandrostenedione in the serum of pregnant women by gas chromatography-mass spectrometry.
2001 Aug
Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells.
2001 Aug 1
Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome.
2001 Aug 9
Sequential first and second trimester screening tests: correlation of the markers' levels in normal versus Down syndrome affected pregnancies.
2001 Dec
Plasma prolactin/oestradiol ratio at 38 weeks gestation predicts the duration of lactational amenorrhoea.
2001 Dec
Unconventional estrogens: estriol, biest, and triest.
2001 Dec
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
Removal of endocrine-disrupting chemicals in activated sludge treatment works.
2001 Dec 15
Treatment of bitches with acquired urinary incontinence with oestriol.
2001 Dec 22-29
An immunoassay for small analytes with theoretical detection limits.
2001 Jul 15
Maternal serum screening for Down's syndrome, open neural tube defects and trisomy 18.
2001 Jun
Sex hormones in experimental autoimmune encephalomyelitis: implications for multiple sclerosis.
2001 Jun
Plasma progesterone, dehydroepiandrosterone sulfate and estriol levels during labor induction with a sustained-release prostaglandin E2 vaginal insert.
2001 Jun
False positive serum biochemical screening and subsequent fetal loss in women less than 35 years of age.
2001 Jun
Determination of estrogens in river water by gas chromatography-negative-ion chemical-ionization mass spectrometry.
2001 Jun 15
Lens culinaris agglutinin-reactive alpha-fetoprotein, an alternative variant to alpha-fetoprotein in prenatal screening for Down's syndrome.
2001 Nov
Identification of negative and positive estrogen response elements in human GnRH upstream promoter in the placental JEG-3 cells.
2001 Nov 26
[Influence of hormonal replacement therapy on bacterial vaginosis in the group of peri- and postmenopausal women].
2001 Oct
ACOG Practice Bulletin. Assessment of risk factors for preterm birth. Clinical management guidelines for obstetrician-gynecologists. Number 31, October 2001. (Replaces Technical Bulletin number 206, June 1995; Committee Opinion number 172, May 1996; Committee Opinion number 187, September 1997; Committee Opinion number 198, February 1998; and Committee Opinion number 251, January 2001).
2001 Oct
[Health Council of Netherlands recommendation 'Serum screening for risk assessment of Down syndrome for all women' poorly supported].
2001 Oct 20
[Cross-over comparison of the pharmacokinetics of estradiol during hormone replacement therapy with estradiol valerate or micronized estradiol].
2001 Sep
Effects of 17-beta estradiol and estriol on NMDA-induced toxicity and apoptosis in primary cultures of rat cortical neurons.
2001 Sep
Enhancement of collagen-induced arthritis in female mice by estrogen receptor blockage.
2001 Sep
Inaccurate estimation of risk in second trimester serum screening for Down syndrome among women who have already had first trimester screening.
2001 Sep
Mammographic density changes during different postmenopausal hormone replacement therapies.
2001 Sep
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
Short term oral estriol treatment restores normal premenopausal vaginal flora to elderly women.
2001 Sep 28
Estradiol valerate/dienogest.
2002
Kinetic comparison of tissue non-specific and placental human alkaline phosphatases expressed in baculovirus infected cells: application to screening for Down's syndrome.
2002
Use of low potency estrogens does not reduce the risk of hip fracture.
2002 Apr
Reduced 11beta-hydroxysteroid dehydrogenase type 2 activity is associated with decreased birth weight centile in pregnancies complicated by asthma.
2002 Apr
Steroid hormone levels during pregnancy and incidence of maternal breast cancer.
2002 Apr
Serial first- and second-trimester Down's syndrome screening tests among IVF-versus naturally-conceived singletons.
2002 Apr
Ligand-specific regulation of proteasome-mediated proteolysis of estrogen receptor-alpha.
2002 Apr
Fetal diaphragmatic hernia and upper limb anomalies suggest Brachmann-de Lange syndrome.
2002 Feb
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
Plasma corticotropin-releasing hormone and unconjugated estriol in human pregnancy: gestational patterns and ability to predict preterm delivery.
2002 Jan
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
Pregnancy outcomes of women with positive serum screening results for Down syndrome and trisomy 18.
2002 Mar
Correlation of ultrasound findings and biochemical markers in the second trimester of pregnancy in fetuses with trisomy 21.
2002 Mar
Estradiol, testosterone, dehydroepiandrosterone and androstenedione: novel derivatives and enantiomers. Interactions with rat liver microsomal cytochrome P450 and antioxidant/radical scavenger activities in vitro.
2002 Mar 10
Patents

Sample Use Guides

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
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).
Name Type Language
ESTRIOL
EP   HSDB   MART.   MI   USP   USP-RS   WHO-DD  
Common Name English
NSC-12169
Code English
ESTRIOL [WHO-DD]
Common Name English
ESTRIOL [EMA EPAR VETERINARY]
Common Name English
ESTRIOL [GREEN BOOK]
Common Name English
ESTRIOL [USP-RS]
Common Name English
AACIFEMINE
Common Name English
INCURIN
Brand Name English
COLPOGYN
Brand Name English
ESTRIOL [EP MONOGRAPH]
Common Name English
TRIHYDROXYESTRIN
Common Name English
16.ALPHA.,17.BETA.-ESTRIOL
Common Name English
ESTRIOL [HSDB]
Common Name English
ESTRIOL [MART.]
Common Name English
16.ALPHA.-HYDROXYESTRADIOL
Code English
ESTRIOL [MI]
Common Name English
1,3,5-ESTRATRIENE-3B,16A,17B-TRIOL
Common Name English
13.BETA.-METHYL-1,3,5(10)-GONATRIENE-3,16.ALPHA.,17.BETA.-TRIOL
Systematic Name English
ESTRIOL [USP]
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,16,17-TRIOL, (16.ALPHA.,17.BETA.)-
Systematic Name English
(16A,17B)-ESTRA-1,3,5(10)-TRIENE-3,16,17-TRIOL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2181
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WHO-ATC G03CC06
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LOINC 21264-7
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LOINC 30510-2
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LOINC 43802-8
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LOINC 15064-9
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LOINC 20466-9
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LOINC 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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LOINC 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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Code System Code Type Description
FDA UNII
FB33469R8E
Created by admin on Fri Jun 25 21:15:11 UTC 2021 , Edited by admin on Fri Jun 25 21:15:11 UTC 2021
PRIMARY
EPA CompTox
50-27-1
Created by admin on Fri Jun 25 21:15:11 UTC 2021 , Edited by admin on Fri Jun 25 21:15:11 UTC 2021
PRIMARY
DRUG CENTRAL
3187
Created by admin on Fri Jun 25 21:15:11 UTC 2021 , Edited by admin on Fri Jun 25 21:15:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL193482
Created by admin on Fri Jun 25 21:15:11 UTC 2021 , Edited by admin on Fri Jun 25 21:15:11 UTC 2021
PRIMARY
CAS
50-27-1
Created by admin on Fri Jun 25 21:15:11 UTC 2021 , Edited by admin on Fri Jun 25 21:15:11 UTC 2021
PRIMARY
HSDB
3590
Created by admin on Fri Jun 25 21:15:11 UTC 2021 , Edited by admin on Fri Jun 25 21:15:11 UTC 2021
PRIMARY
NCI_THESAURUS
C80154
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PRIMARY
RXCUI
4094
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PRIMARY RxNorm
DRUG BANK
DB04573
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PRIMARY
PUBCHEM
5756
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PRIMARY
MESH
D004964
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PRIMARY
EVMPD
SUB01971MIG
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PRIMARY
MERCK INDEX
M5032
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PRIMARY Merck Index
ECHA (EC/EINECS)
200-022-2
Created by admin on Fri Jun 25 21:15:11 UTC 2021 , Edited by admin on Fri Jun 25 21:15:11 UTC 2021
PRIMARY
WIKIPEDIA
Estriol
Created by admin on Fri Jun 25 21:15:11 UTC 2021 , Edited by admin on Fri Jun 25 21:15:11 UTC 2021
PRIMARY
IUPHAR
2821
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PRIMARY
USP_CATALOG
1254508
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PRIMARY USP-RS