Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H24O4.H2O |
Molecular Weight | 322.396 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.C[C@]12CC[C@H]3[C@@H](CCC4=CC(O)=CC=C34)[C@@H]1[C@@H](O)[C@@H](O)[C@@H]2O
InChI
InChIKey=XRJNAPXFAXBPAM-BVTDNVAGSA-N
InChI=1S/C18H24O4.H2O/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22;/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3;1H2/t12-,13-,14-,15-,16-,17+,18+;/m1./s1
Molecular Formula | C18H24O4 |
Molecular Weight | 304.3808 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Estetrol is the natural human fetal selective estrogen receptor modulator. It is synthesized exclusively by the human fetal liver during pregnancy. Estetrol has a moderate affinity for human estrogen A receptor (ERa) and estrogen B receptor (ERb). Estetrol may be suitable as a potential drug for human use in applications such as hormone replacement therapy (vaginal atrophy, hot flushes), contraception and osteoporosis. The most common drug-related adverse events were lower abdominal pain, nausea, headache, dysmenorrhoea, breast enlargement and acne. Estetrol had been in clinical trials for the treatment of breast and prostate cancers.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18464023 |
4.9 nM [Ki] | ||
Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18464023 |
19.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
17.9 ng/mL |
14.2 mg single, oral dose: 14.2 mg route of administration: Oral experiment type: SINGLE co-administered: DROSPIRENONE |
ESTETROL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
56.59 ng/mL EXPERIMENT https://doi.org/10.3390/ijms24119718 |
45 mg single, oral dose: 45 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESTETROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
8.01 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28267365 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESTETROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
87.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28267365 |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ESTETROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
59.1 ng × h/mL |
14.2 mg single, oral dose: 14.2 mg route of administration: Oral experiment type: SINGLE co-administered: DROSPIRENONE |
ESTETROL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
321.05 ng × h/mL EXPERIMENT https://doi.org/10.3390/ijms24119718 |
45 mg single, oral dose: 45 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESTETROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
194.2 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28267365 |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ESTETROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27 h |
14.2 mg single, oral dose: 14.2 mg route of administration: Oral experiment type: SINGLE co-administered: DROSPIRENONE |
ESTETROL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
26.64 h EXPERIMENT https://doi.org/10.3390/ijms24119718 |
45 mg single, oral dose: 45 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESTETROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
52% |
14.2 mg single, oral dose: 14.2 mg route of administration: Oral experiment type: SINGLE co-administered: DROSPIRENONE |
ESTETROL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg single, oral Highest studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
|
15 mg 1 times / day multiple, oral Minumum effective dose Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: uterine bleedin... AEs leading to discontinuation/dose reduction: uterine bleedin (grade 3, 2%) Sources: |
60 mg 1 times / day multiple, oral Studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
uterine bleedin | grade 3, 2% Disc. AE |
15 mg 1 times / day multiple, oral Minumum effective dose Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Interaction of native alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin and their hydroxypropyl derivatives with selected organic low molecular mass compounds at elevated and subambient temperature under RP-HPLC conditions. | 2008 Aug |
|
Clinical applications for estetrol. | 2009 Mar |
|
[Estrogen: estrone (E1), estradiol (E2), estriol (E3) and estetrol (E4)]. | 2010 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02817828
Curator's Comment: in combination with 3 mg drospirenone tablets
15 mg administered once daily for 13 consecutive cycles following a 24/4-day regimen.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18464023
Binding of Estetrol at the glucocorticoid, progesterone and
testosterone receptors was only 11–15% at a concentration of 10 uM/l. Estetrol at a high concentration of 10 uM/l did not inhibit the major cytochrome P450 enzymes CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A4.
Substance Class |
Chemical
Created
by
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Edited
Wed Apr 02 04:22:38 GMT 2025
by
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on
Wed Apr 02 04:22:38 GMT 2025
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KC3GI9UM9V
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Validated (UNII)
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C169963
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PARENT -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |
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