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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Estetrol (DB12235)

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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

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Associated Therapies

• Oral Contraceptives

Contraindications & Blackbox Warnings

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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

Target	Actions	Organism
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

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abaloparatide	The therapeutic efficacy of Abaloparatide can be decreased when used in combination with Estetrol.
Abametapir	The serum concentration of Estetrol can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Estetrol can be increased when combined with Abatacept.
Abciximab	The risk or severity of adverse effects can be increased when Estetrol is combined with Abciximab.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Estetrol.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Estetrol.
Acarbose	The therapeutic efficacy of Acarbose can be decreased when used in combination with Estetrol.
Acebutolol	The risk or severity of hyperkalemia can be increased when Acebutolol is combined with Estetrol.
Aceclofenac	The risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Estetrol.
Acemetacin	The risk or severity of hyperkalemia can be increased when Acemetacin is combined with Estetrol.

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Food Interactions

• Take with or without food. Take at the same time each day.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Estetrol monohydrate	KC3GI9UM9V	2055649-81-3	XRJNAPXFAXBPAM-BVTDNVAGSA-N

International/Other Brands

Donesta

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Drovelis	Estetrol monohydrate (14.2 mg) + Drospirenone (3 mg)	Tablet, film coated	Oral	Gedeon Richter Plc.	2021-10-12	Not applicable
Drovelis	Estetrol monohydrate (14.2 mg) + Drospirenone (3 mg)	Tablet, film coated	Oral	Gedeon Richter Plc.	2021-10-12	Not applicable
Drovelis	Estetrol monohydrate (14.2 mg) + Drospirenone (3 mg)	Tablet, film coated	Oral	Gedeon Richter Plc.	2021-10-12	Not applicable
Drovelis	Estetrol monohydrate (14.2 mg) + Drospirenone (3 mg)	Tablet, film coated	Oral	Gedeon Richter Plc.	2021-10-12	Not applicable
Lydisilka	Estetrol monohydrate (14.2 mg) + Drospirenone (3 mg)	Tablet, film coated	Oral	Estetra Sprl	2021-10-15	Not applicable
Lydisilka	Estetrol monohydrate (14.2 mg) + Drospirenone (3 mg)	Tablet, film coated	Oral	Estetra Sprl	2021-10-15	Not applicable
Lydisilka	Estetrol monohydrate (14.2 mg) + Drospirenone (3 mg)	Tablet, film coated	Oral	Estetra Sprl	2021-10-15	Not applicable
Lydisilka	Estetrol monohydrate (14.2 mg) + Drospirenone (3 mg)	Tablet, film coated	Oral	Estetra Sprl	2021-10-15	Not applicable
Nextstellis	Estetrol monohydrate (15 mg) + Drospirenone (3 mg)	Tablet	Oral	Searchlight Pharma Inc	2021-06-15	Not applicable
Nextstellis	Estetrol monohydrate (14.2 mg/1) + Drospirenone (3 mg/1)	Tablet	Oral	Mayne Pharma	2021-04-16	Not applicable

Categories

Drug Categories

• Adrenal Cortex Hormones
• Contraceptives, Oral
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A4 Substrates (strength unknown)
• Cytochrome P-450 Substrates
• Estradiol Congeners
• Estranes
• Estrenes
• Estrogen Contraceptives
• Estrogens
• Estrogens, agonists
• Fused-Ring Compounds
• Gonadal Hormones
• Gonadal Steroid Hormones
• Hormonal Contraceptives for Systemic Use
• Hormones
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Steroids
• UGT2B7 substrates

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]

External Links

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

Phase	Status	Purpose	Conditions	Count
3	Active Not Recruiting	Treatment	Menopausal Symptoms / Vasomotor Symptoms Associated With Menopause	1
3	Completed	Prevention	Contraception	2
3	Recruiting	Prevention	Safety	1
3	Recruiting	Treatment	Menopausal Symptoms / Vasomotor Symptoms Associated With Menopause	1
2	Active Not Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19)	1
2	Completed	Prevention	Contraception	1
2	Completed	Treatment	Breast Cancer	1
2	Completed	Treatment	Healthy Subjects (HS)	1
2	Completed	Treatment	Hot Flashes	1
2	Completed	Treatment	Prostatic Neoplasms	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral
Tablet	Oral

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US7732430	No	2010-06-08	2025-03-02

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	233-236	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1210710.htm
boiling point (°C)	491.9±45.0	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1210710.htm
logP	2.62	https://www.embopress.org/doi/full/10.15252/emmm.201404112
pKa	10.22±0.70	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1210710.htm

Predicted Properties

Property	Value	Source
logP	1.67	ChemAxon
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å2	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.55 m3·mol-1	ChemAxon
Polarizability	33.88 Å3	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Estrogen receptor alpha

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]

Details2. Estrogen receptor beta

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]

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