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.[H][C@@]12[C@@H](O)[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=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 | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H24O4 |
Molecular Weight | 304.3808 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.34 |
healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 6 Sources: Page: p.34 |
|
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: Page: p.855 |
unhealthy, ADULT n = 49 Health Status: unhealthy Condition: reproductive system disease Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 49 Sources: Page: p.855 |
Disc. AE: uterine bleedin... AEs leading to discontinuation/dose reduction: uterine bleedin (grade 3, 2%) Sources: Page: p.855 |
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: Page: p.1837 |
unhealthy, ADULT n = 3 Health Status: unhealthy Condition: breast cancer Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 3 Sources: Page: p.1837 |
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: Page: p.855 |
unhealthy, ADULT n = 49 Health Status: unhealthy Condition: reproductive system disease Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 49 Sources: Page: p.855 |
PubMed
Title | Date | PubMed |
---|---|---|
Simple chamber for temperature-controlled planar chromatography. | 2002 Sep 20 |
|
Characterization of human fetal cord blood steroid profiles in relation to fetal sex and mode of delivery using temperature-dependent inclusion chromatography and principal component analysis (PCA). | 2007 Aug 15 |
|
In vitro effects of estetrol on receptor binding, drug targets and human liver cell metabolism. | 2008 |
|
A new route of synthesis of estetrol. | 2008 |
|
Estetrol review: profile and potential clinical applications. | 2008 |
|
Ovulation inhibition by estetrol in an in vivo model. | 2008 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
admin
on
Edited
Thu Jul 06 20:43:25 UTC 2023
by
admin
on
Thu Jul 06 20:43:25 UTC 2023
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Record UNII |
KC3GI9UM9V
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Record Status |
Validated (UNII)
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300000014640
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135391051
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2539035
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KC3GI9UM9V
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C169963
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |
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