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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H32O9
Molecular Weight 488.5269
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRIOL SUCCINATE

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1C[C@@H](OC(=O)CCC(O)=O)[C@@H]2OC(=O)CCC(O)=O

InChI

InChIKey=VBRVDDFOBZNCPF-BRSFZVHSSA-N
InChI=1S/C26H32O9/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)/t17-,18-,19+,20-,25+,26+/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H32O9
Molecular Weight 488.5269
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
234.42 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ovestin
Primary
Ovestin
Primary
Ovestin

Cmax

ValueDoseCo-administeredAnalytePopulation
60.57 pg/mL
20 μg single, vaginal
ESTRIOL plasma
Homo sapiens
106.4 pg/mL
50 μg single, vaginal
ESTRIOL plasma
Homo sapiens
13.77 pg/mL
20 μg 1 times / day steady-state, vaginal
ESTRIOL plasma
Homo sapiens
22.8 pg/mL
50 μg 1 times / day steady-state, vaginal
ESTRIOL plasma
Homo sapiens
0.546 nM
0.5 mg single, vaginal
ESTRIOL serum
Homo sapiens
68 pg/mL
0.125 mg 1 times / day multiple, vaginal
ESTRIOL plasma
Homo sapiens
155 pg/mL
0.5 mg 1 times / day multiple, vaginal
ESTRIOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
171.65 pg × h/mL
20 μg single, vaginal
ESTRIOL plasma
Homo sapiens
406.75 pg × h/mL
50 μg single, vaginal
ESTRIOL plasma
Homo sapiens
36.33 pg × h/mL
20 μg 1 times / day steady-state, vaginal
ESTRIOL plasma
Homo sapiens
73.71 pg × h/mL
50 μg 1 times / day steady-state, vaginal
ESTRIOL plasma
Homo sapiens
2.145 nM × h
0.5 mg single, vaginal
ESTRIOL serum
Homo sapiens
5643 pg × h/mL
0.125 mg 1 times / day multiple, vaginal
ESTRIOL plasma
Homo sapiens
18323 pg × h/mL
0.5 mg 1 times / day multiple, vaginal
ESTRIOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.59 h
20 μg single, vaginal
ESTRIOL plasma
Homo sapiens
1.65 h
50 μg single, vaginal
ESTRIOL plasma
Homo sapiens
2.72 h
0.5 mg single, vaginal
ESTRIOL serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
ESTRIOL serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
AS13K2DY03
Record Status Validated (UNII)
Record Version