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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O3
Molecular Weight 288.3814
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Estriol

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

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
Biochemical markers for preterm labor and birth: what is their role in the care of pregnant women?
1999 Mar-Apr
[Hormone replacement therapy in women with arterial hypertension in peri- and postmenopause: hemodynamic effects].
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
First-trimester increased nuchal translucency and fetal hypokinesia associated with Zellweger syndrome.
2001 Apr
Comparison of triple serum screening and pregnancy outcome in oocyte donation versus IVF 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
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
Plasma prolactin/oestradiol ratio at 38 weeks gestation predicts the duration of lactational amenorrhoea.
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
[Trisomy 21 screening: value of ultrasound and serum markers in a combined approach].
2001 Feb
Low-dose estrogen therapy ameliorates experimental autoimmune encephalomyelitis in two different inbred mouse strains.
2001 Feb 1
Evaluation of effect of analytical imprecision in maternal serum screening for Down's syndrome.
2001 Jan
Repeat testing in antenatal screening for Down syndrome using dimeric inhibin-A in combination with other maternal serum markers.
2001 Jan
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
[Hormone therapy in climacteric. Different effects of estrogen and gestagen on the risk of breast and endometrial cancer].
2001 Jan 31
Hormone replacement therapy after invasive ovarian serous cystadenocarcinoma treatment: the effect on survival.
2001 Jan-Feb
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
Mammographic breast density during hormone replacement therapy: effects of continuous combination, unopposed transdermal and low-potency estrogen regimens.
2001 Mar
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
Gas chromatography-mass spectrometric determination of activity of human placental aromatase using 16alpha-hydroxyandrostenedione as a substrate.
2001 May
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
Identification of negative and positive estrogen response elements in human GnRH upstream promoter in the placental JEG-3 cells.
2001 Nov 26
[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
Short term oral estriol treatment restores normal premenopausal vaginal flora to elderly women.
2001 Sep 28
Estradiol valerate/dienogest.
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
Plasma corticotropin-releasing hormone and unconjugated estriol in human pregnancy: gestational patterns and ability to predict preterm delivery.
2002 Jan
Topical estrogens combined with argon plasma coagulation in the management of epistaxis in hereditary hemorrhagic telangiectasia.
2002 Mar
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
ESTRIOL [JAN]
Common Name English
NSC-12169
Code 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
ESTRIOL [USP MONOGRAPH]
Common 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
ESTRA-1,3,5(10)-TRIENE-3,16,17-TRIOL, (16.ALPHA.,17.BETA.)-
Systematic Name English
Estriol [WHO-DD]
Common 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
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
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
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
LOINC 2253-3
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Code System Code Type Description
FDA UNII
FB33469R8E
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID9022366
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
DRUG CENTRAL
3187
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
RS_ITEM_NUM
1254508
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PRIMARY
ChEMBL
CHEMBL193482
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PRIMARY
CAS
50-27-1
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
HSDB
3590
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
NCI_THESAURUS
C80154
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
NSC
12169
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
RXCUI
4094
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB04573
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PRIMARY
PUBCHEM
5756
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PRIMARY
WIKIPEDIA
Estriol (medication)
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
SMS_ID
100000092668
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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
DAILYMED
FB33469R8E
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-022-2
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PRIMARY
CHEBI
27974
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PRIMARY
WIKIPEDIA
Estriol
Created by admin on Wed Jul 05 22:47:18 UTC 2023 , Edited by admin on Wed Jul 05 22:47:18 UTC 2023
PRIMARY
IUPHAR
2821
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PRIMARY