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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H30O9.2Na
Molecular Weight 532.4905
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRIOL SODIUM SUCCINATE

SMILES

[Na+].[Na+].[H][C@@]12C[C@@H](OC(=O)CCC([O-])=O)[C@H](OC(=O)CCC([O-])=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

InChI

InChIKey=WHMFJWUAHROXHB-KQAQVGESSA-L
InChI=1S/C26H32O9.2Na/c1-26-11-10-17-16-5-3-15(27)12-14(16)2-4-18(17)19(26)13-20(34-23(32)8-6-21(28)29)25(26)35-24(33)9-7-22(30)31;;/h3,5,12,17-20,25,27H,2,4,6-11,13H2,1H3,(H,28,29)(H,30,31);;/q;2*+1/p-2/t17-,18-,19+,20-,25+,26+;;/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
Biochemical markers for preterm labor and birth: what is their role in the care of pregnant women?
1999 Mar-Apr
Female sex steroids: effects upon microglial cell activation.
2000 Nov 1
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
[Hormone replacement therapy in women with arterial hypertension in peri- and postmenopause: hemodynamic effects].
2001
Triple-test screening in in vitro fertilization pregnancies.
2001 Apr
[Effect of estriol treatment per vaginam before Burch culposuspension].
2001 Apr
Second trimester maternal serum analytes in triploid pregnancies: correlation with phenotype and sex chromosome complement.
2001 Aug
Sequential first and second trimester screening tests: correlation of the markers' levels in normal versus Down syndrome affected pregnancies.
2001 Dec
Treatment of bitches with acquired urinary incontinence with oestriol.
2001 Dec 22-29
Estrogenic potency of chemicals detected in sewage treatment plant effluents as determined by in vivo assays with Japanese medaka (Oryzias latipes).
2001 Feb
Low-dose estrogen therapy ameliorates experimental autoimmune encephalomyelitis in two different inbred mouse strains.
2001 Feb 1
The physiological role of estriol during human fetal development is to act as antioxidant at lipophilic milieus of the central nervous system.
2001 Jan
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.
2001 Jan
In vivo regulation of syndecan-3 expression in the rat uterus by 17 beta-estradiol.
2001 Jan 5
Mammographic breast density during hormone replacement therapy: effects of continuous combination, unopposed transdermal and low-potency estrogen regimens.
2001 Mar
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.
2001 Mar-Apr
Estriol improves membrane fluidity of erythrocytes by the nitric oxide-dependent mechanism: an electron paramagnetic resonance study.
2001 May
Effect of incorrect gestational dating on Down's syndrome and neural tube risk assessment.
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
Lens culinaris agglutinin-reactive alpha-fetoprotein, an alternative variant to alpha-fetoprotein in prenatal screening for Down's syndrome.
2001 Nov
[Cross-over comparison of the pharmacokinetics of estradiol during hormone replacement therapy with estradiol valerate or micronized estradiol].
2001 Sep
Fetal diaphragmatic hernia and upper limb anomalies suggest Brachmann-de Lange syndrome.
2002 Feb
Maternal serum triple analyte screening in pregnancy.
2002 Mar 1
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 SODIUM SUCCINATE
MART.  
Common Name English
Estriol disodium succinate [WHO-DD]
Common Name English
ESTRIOL 16,17-BIS(SODIUM HEMISUCCINATE) [MI]
Common Name English
ESTRIOL 16,17-BIS(HYDROGEN SUCCINATE) DISODIUM SALT
Common Name English
DISODIUM 3-HYDROXY-ESTRA-1,3,5(10)-TRIENE-16.ALPHA.,17.BETA.-DIYL DISUCCINATE
Common Name English
ESTRIOL SODIUM SUCCINATE [MART.]
Common Name English
SYNAPAUSE
Brand Name English
ESTRIOL DISODIUM SUCCINATE
WHO-DD  
Common Name English
ORGASTYPTIN
Brand Name English
STIPTANON
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C478
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
Code System Code Type Description
FDA UNII
64I100CU65
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
PRIMARY
EVMPD
SUB01972MIG
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
PRIMARY
SMS_ID
100000087275
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID10920967
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
PRIMARY
PUBCHEM
164538
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
PRIMARY
NCI_THESAURUS
C80803
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
PRIMARY
CAS
113-22-4
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
PRIMARY
MERCK INDEX
m5032
Created by admin on Fri Dec 15 16:12:51 GMT 2023 , Edited by admin on Fri Dec 15 16:12:51 GMT 2023
PRIMARY Merck Index