Estetrol

Identification

Summary

Estetrol is an estrogen used in combination with drospirenone for oral contraception.

Brand Names
Nextstellis 28 Day
Generic Name
Estetrol
DrugBank Accession Number
DB12235
Background

Naturally or synthetically produced steroid estrogens have a wide range of pharmaceutical uses ranging from hormonal contraception to the treatment of menopausal symptoms.15 Estetrol (E4) is a native estrogen occurring naturally during pregnancy, but can be synthesized from a plant source and used for contraception.14 It is more potent and is safer than the synthetic estrogen ethinylestradiol (EE2) found in 97% of oral contraceptive pills, reducing the environmental accumulation of unwanted endocrine disrupting chemicals (EDCs) that often lead to harmful epigenetic effects.15

On April 15 2021, Mayne Pharma Group Limited and Mithra Pharmaceuticals were granted FDA approval for the oral contraceptive Estelle/Nextstellis, a combination of drospirenone and estetrol. Estetrol is the first new estrogen introduced to the USA in over 50 years and is the first approved estetrol product in the world. The combination of drospirenone and estetrol offers a new choice with a favourable safety profile for women seeking contraceptive therapy.14 In Canada, Nextstellis was approved for use in March 2021; it was developed by Mithra and is marketed by Searchlight Pharma.18

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 304.3808
Monoisotopic: 304.167459256
Chemical Formula
C18H24O4
Synonyms
  • 15α-hydroxyestriol
  • Estetrol
  • Estétrol
  • Estetrolum
  • Oestetrol

Pharmacology

Indication

Estetrol is indicated in combination with drospirenone for the prevention of pregnancy.13

Pharmacology
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Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Estetrol prevents pregnancy by suppressing ovulation.9,13

Mechanism of action

Estetrol is a synthetic analogue of a naturally occurring estrogen present during pregnancy, demonstrating selectivity for both estrogen receptor-α (ER-α) and ER-β and suppressing ovulation.13 Estetrol binds with a low to moderate affinity human estrogen receptor alpha (ER alpha) and ER beta with a preference for ER alpha.8 Estetrol demonstrates a unique mechanism of action via tissue selective activity, showing estrogen receptor agonist activity on the vagina, the uterus and the endometrium, and negative estrogenic activity on breast tissue.12,18

TargetActionsOrganism
UEstrogen receptor alpha
agonist
modulator
regulator
Humans
UEstrogen receptor beta
agonist
Humans
Absorption

Estetrol is rapidly absorbed from the gastrointestinal tract. The Cmax of estetrol is 18 ng/mL according to the results of a pharmacokinetic study, with an AUC of 36.4 ng•h/mL. When estetrol and drospirenone are taken in a single product, maximum serum concentrations of approximately 48.7 ng/mL are achieved within 1-3 h. Bioavailability of the combination ranges between 76 and 85%.17 The Tmax can range from 0.5 to 2 hours and time to steady state is approximately 4 days, according to the results of one clinical study.13

Volume of distribution

Limited distribution of estetrol into red blood cells has been demonstrated.17

Protein binding

Estetrol is 46-50% bound to plasma proteins.13 Estetrol does not bind to Sex Hormone Binding Globulin (SHBG). In one study, estetrol showed moderate binding to human plasma proteins (45.5%-50.4%) and human serum albumin (58.6%) with low binding to human alpha-glycoprotein (11.2%).17

Metabolism

Estretol is heavily metabolized after oral administration.17 Phase 2 metabolism of estrogen forms glucuronide and sulfate conjugates with negligible in-vitro estrogenic activity. In vitro metabolism studies demonstrate that UGT2B7 catalyzes the formation of E4-16-glucuronide. Estetrol is combined with drospirenone in a product. The hepatic cytochrome enzyme CYP3A4 metabolizes drospirenone to two primary metabolites: the acid form of drospirenone through the opening of the lactone ring and the 4,5­ dihydrodrospirenone formed by reduction, followed by sulfation. Both metabolites are pharmacologically inactive.13,17

Route of elimination

Estrogens are generally excreted as sulfated and glucuronidated derivatives.11 Approximately 69% of a dose of estetrol is excreted in the urine, and about 22% is excreted in the feces as unchanged drug.13

Half-life

The elimination half-life of estetrol is approximately 27 hours.13 Half-life may range between 19-40 hours.7

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

LD50 information for estetrol is not readily available in the literature. Subjects receiving a dose of 20 mg, 40 mg or 60 mg of estetrol per day over 12 weeks were tolerated without dose-limiting toxicity.10 Symptoms that may occur in association with overdose, based on existing information on overdosage with oral contraceptives include nausea, vomiting, and vaginal bleeding. In one clinical study, 1 of 32 healthy research subjects receiving a dose of 75 mg of estretol with 15 mg of drospirenone for 10 days experienced deep vein thrombosis of the lower right limb. There is no known antidote to an estretol overdose; conduct laboratory testing for electrolytes and evidence of metabolic acidosis and provide symptomatic treatment.17

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Estetrol.
AbametapirThe serum concentration of Estetrol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Estetrol can be increased when combined with Abatacept.
AbciximabThe risk or severity of adverse effects can be increased when Estetrol is combined with Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Estetrol.
AbirateroneThe metabolism of Estetrol can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Estetrol.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Estetrol.
AcebutololThe risk or severity of hyperkalemia can be increased when Acebutolol is combined with Estetrol.
AceclofenacThe risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Estetrol.
Interactions
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Food Interactions
  • Take with or without food. Take at the same time each day.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Estetrol monohydrateKC3GI9UM9V2055649-81-3XRJNAPXFAXBPAM-BVTDNVAGSA-N
International/Other Brands
Donesta
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
NextstellisEstetrol monohydrate (15 mg) + Drospirenone (3 mg)TabletOralSearchlight Pharma Inc2021-06-15Not applicableCanada flag
NextstellisEstetrol monohydrate (14.2 mg/1) + Drospirenone (3 mg/1)TabletOralMayne Pharma2021-04-16Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-hydroxysteroids / 17-hydroxysteroids / 16-alpha-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / Cyclic alcohols and derivatives / Polyols / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 15-hydroxysteroid / 16-alpha-hydroxysteroid / 16-hydroxysteroid / 17-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aromatic homopolycyclic compound / Benzenoid / Cyclic alcohol
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
ENB39R14VF
CAS number
15183-37-6
InChI Key
AJIPIJNNOJSSQC-NYLIRDPKSA-N
InChI
InChI=1S/C18H24O4/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/t12-,13-,14-,15-,16-,17+,18+/m1/s1
IUPAC Name
(1R,2R,3R,3aS,3bR,9bS,11aS)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,2,3,7-tetrol
SMILES
[H][C@@]12[C@@H](O)[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C=C3CC[C@@]21[H]

References

Synthesis Reference

Johannes Jan Platteeuw, Herman Jan Tijmen, Coelingh Bennink, Franciscus Wilhelmus, Petrus Damen, Michiel Christian, Alexander Van Vliet. (2013).Process for the preparation of estetrol. (WO2013012328A1).https://patents.google.com/patent/WO2013012328A1/en18

General References
  1. Apter D, Zimmerman Y, Beekman L, Mawet M, Maillard C, Foidart JM, Coelingh Bennink HJT: Estetrol combined with drospirenone: an oral contraceptive with high acceptability, user satisfaction, well-being and favourable body weight control. Eur J Contracept Reprod Health Care. 2017 Aug;22(4):260-267. doi: 10.1080/13625187.2017.1336532. Epub 2017 Jun 22. [Article]
  2. Montt-Guevara MM, Giretti MS, Russo E, Giannini A, Mannella P, Genazzani AR, Genazzani AD, Simoncini T: Estetrol Modulates Endothelial Nitric Oxide Synthesis in Human Endothelial Cells. Front Endocrinol (Lausanne). 2015 Jul 22;6:111. doi: 10.3389/fendo.2015.00111. eCollection 2015. [Article]
  3. Gaspard U, Taziaux M, Mawet M, Jost M, Gordenne V, Coelingh Bennink HJT, Lobo RA, Utian WH, Foidart JM: A multicenter, randomized study to select the minimum effective dose of estetrol (E4) in postmenopausal women (E4Relief): part 1. Vasomotor symptoms and overall safety. Menopause. 2020 Aug;27(8):848-857. doi: 10.1097/GME.0000000000001561. [Article]
  4. Abot A, Fontaine C, Buscato M, Solinhac R, Flouriot G, Fabre A, Drougard A, Rajan S, Laine M, Milon A, Muller I, Henrion D, Adlanmerini M, Valera MC, Gompel A, Gerard C, Pequeux C, Mestdagt M, Raymond-Letron I, Knauf C, Ferriere F, Valet P, Gourdy P, Katzenellenbogen BS, Katzenellenbogen JA, Lenfant F, Greene GL, Foidart JM, Arnal JF: The uterine and vascular actions of estetrol delineate a distinctive profile of estrogen receptor alpha modulation, uncoupling nuclear and membrane activation. EMBO Mol Med. 2014 Oct;6(10):1328-46. doi: 10.15252/emmm.201404112. [Article]
  5. Grandi G, Del Savio MC, Lopes da Silva-Filho A, Facchinetti F: Estetrol (E4): the new estrogenic component of combined oral contraceptives. Expert Rev Clin Pharmacol. 2020 Apr;13(4):327-330. doi: 10.1080/17512433.2020.1750365. Epub 2020 Apr 7. [Article]
  6. Coelingh Bennink HJT, Verhoeven C, Zimmerman Y, Visser M, Foidart JM, Gemzell-Danielsson K: Pharmacokinetics of the fetal estrogen estetrol in a multiple-rising-dose study in postmenopausal women. Climacteric. 2017 Jun;20(3):285-289. doi: 10.1080/13697137.2017.1291608. Epub 2017 Mar 7. [Article]
  7. Visser M, Holinka CF, Coelingh Bennink HJ: First human exposure to exogenous single-dose oral estetrol in early postmenopausal women. Climacteric. 2008;11 Suppl 1:31-40. doi: 10.1080/13697130802056511. [Article]
  8. Visser M, Foidart JM, Coelingh Bennink HJ: In vitro effects of estetrol on receptor binding, drug targets and human liver cell metabolism. Climacteric. 2008;11 Suppl 1:64-8. doi: 10.1080/13697130802050340. [Article]
  9. Duijkers IJ, Klipping C, Zimmerman Y, Appels N, Jost M, Maillard C, Mawet M, Foidart JM, Coelingh Bennink HJ: Inhibition of ovulation by administration of estetrol in combination with drospirenone or levonorgestrel: Results of a phase II dose-finding pilot study. Eur J Contracept Reprod Health Care. 2015;20(6):476-89. doi: 10.3109/13625187.2015.1074675. [Article]
  10. Schmidt M, Lenhard H, Hoenig A, Zimmerman Y, Krijgh J, Jansen M, Coelingh Bennink HJT: Tumor suppression, dose-limiting toxicity and wellbeing with the fetal estrogen estetrol in patients with advanced breast cancer. J Cancer Res Clin Oncol. 2020 Nov 26. pii: 10.1007/s00432-020-03472-8. doi: 10.1007/s00432-020-03472-8. [Article]
  11. Thomas MP, Potter BV: The structural biology of oestrogen metabolism. J Steroid Biochem Mol Biol. 2013 Sep;137:27-49. doi: 10.1016/j.jsbmb.2012.12.014. Epub 2013 Jan 4. [Article]
  12. Singer CF, Bennink HJ, Natter C, Steurer S, Rudas M, Moinfar F, Appels N, Visser M, Kubista E: Antiestrogenic effects of the fetal estrogen estetrol in women with estrogen-receptor positive early breast cancer. Carcinogenesis. 2014 Nov;35(11):2447-51. doi: 10.1093/carcin/bgu144. Epub 2014 Jul 5. [Article]
  13. FDA Approved Drug Products: NEXTSTELLIS (drospirenone and estetrol) tablets for oral use [Link]
  14. Joint press release, Mayne Pharma and Mithra: MAYNE PHARMA AND MITHRA ANNOUNCE FDA APPROVAL OF NEW ORAL CONTRACEPTIVE NEXTSTELLIS [Link]
  15. Mithra Women's Health: E4 Paves the Road Towards a Revolutionary Era of Environmental Friendly Medicines [Link]
  16. Cayman Chem MSDS: Estetrol hydrate [Link]
  17. Product monograph: Nexstellis (estetrol and drospirenone) oral tablets [Link]
  18. Newswire: Mithra and Searchlight Pharma Announce Nextstellis® Approval in Canada [Link]
PubChem Compound
27125
PubChem Substance
347828514
ChemSpider
25245
BindingDB
158505
RxNav
2539031
ChEBI
142773
ChEMBL
CHEMBL1230314
ZINC
ZINC000005764481
PDBe Ligand
4OH
Wikipedia
Estetrol
PDB Entries
3l03

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedPreventionContraception2
3RecruitingPreventionSafety1
3RecruitingTreatmentMenopausal Symptoms / Vasomotor Symptoms Associated With Menopause2
2Active Not RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19)1
2CompletedPreventionContraception1
2CompletedTreatmentBreast Cancer1
2CompletedTreatmentHealthy Subjects (HS)1
2CompletedTreatmentHot Flashes1
2CompletedTreatmentProstatic Neoplasms1
1CompletedNot AvailableContraception1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7732430No2005-03-022025-03-02US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)233-236https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1210710.htm
boiling point (°C)491.9±45.0https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1210710.htm
logP2.62https://www.embopress.org/doi/full/10.15252/emmm.201404112
pKa10.22±0.70https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1210710.htm
Predicted Properties
PropertyValueSource
logP1.67ChemAxon
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.55 m3·mol-1ChemAxon
Polarizability33.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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insights and accelerate drug research.
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Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Modulator
Regulator
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Gaspard U, Taziaux M, Mawet M, Jost M, Gordenne V, Coelingh Bennink HJT, Lobo RA, Utian WH, Foidart JM: A multicenter, randomized study to select the minimum effective dose of estetrol (E4) in postmenopausal women (E4Relief): part 1. Vasomotor symptoms and overall safety. Menopause. 2020 Aug;27(8):848-857. doi: 10.1097/GME.0000000000001561. [Article]
  2. Abot A, Fontaine C, Buscato M, Solinhac R, Flouriot G, Fabre A, Drougard A, Rajan S, Laine M, Milon A, Muller I, Henrion D, Adlanmerini M, Valera MC, Gompel A, Gerard C, Pequeux C, Mestdagt M, Raymond-Letron I, Knauf C, Ferriere F, Valet P, Gourdy P, Katzenellenbogen BS, Katzenellenbogen JA, Lenfant F, Greene GL, Foidart JM, Arnal JF: The uterine and vascular actions of estetrol delineate a distinctive profile of estrogen receptor alpha modulation, uncoupling nuclear and membrane activation. EMBO Mol Med. 2014 Oct;6(10):1328-46. doi: 10.15252/emmm.201404112. [Article]
  3. Benoit T, Valera MC, Fontaine C, Buscato M, Lenfant F, Raymond-Letron I, Tremollieres F, Soulie M, Foidart JM, Game X, Arnal JF: Estetrol, a Fetal Selective Estrogen Receptor Modulator, Acts on the Vagina of Mice through Nuclear Estrogen Receptor alpha Activation. Am J Pathol. 2017 Nov;187(11):2499-2507. doi: 10.1016/j.ajpath.2017.07.013. Epub 2017 Aug 19. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Montt-Guevara MM, Giretti MS, Russo E, Giannini A, Mannella P, Genazzani AR, Genazzani AD, Simoncini T: Estetrol Modulates Endothelial Nitric Oxide Synthesis in Human Endothelial Cells. Front Endocrinol (Lausanne). 2015 Jul 22;6:111. doi: 10.3389/fendo.2015.00111. eCollection 2015. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Jeong H: Altered drug metabolism during pregnancy: hormonal regulation of drug-metabolizing enzymes. Expert Opin Drug Metab Toxicol. 2010 Jun;6(6):689-99. doi: 10.1517/17425251003677755. [Article]
  2. FDA Approved Drug Products: NEXTSTELLIS (drospirenone and estetrol) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Gall WE, Zawada G, Mojarrabi B, Tephly TR, Green MD, Coffman BL, Mackenzie PI, Radominska-Pandya A: Differential glucuronidation of bile acids, androgens and estrogens by human UGT1A3 and 2B7. J Steroid Biochem Mol Biol. 1999 Jul-Aug;70(1-3):101-8. doi: 10.1016/s0960-0760(99)00088-6. [Article]
  2. FDA Approved Drug Products: NEXTSTELLIS (drospirenone and estetrol) tablets for oral use [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: NEXTSTELLIS (drospirenone and estetrol) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Product monograph: Nexstellis (estetrol and drospirenone) oral tablets [Link]

Drug created on October 20, 2016 21:41 / Updated on April 23, 2021 09:38