Esterified estrogens

Identification

Summary

Esterified estrogens is a female hormone used to treat conditions related to estrogen deficiency and moderate to severe vasomotor menopausal symptoms in women.

Brand Names
Covaryx, Menest
Generic Name
Esterified estrogens
DrugBank Accession Number
DB09381
Background

Esterified estrogens contain a mixture of estrogenic substances; the principle component is estrone. Preparations contain 75% to 85% sodium estrone sulfate and 6% to 15% sodium equilin sulfate such that the total is not <90%. Esterified estrogens are a man-made mixture of estrogens that are used to treat symptoms of menopause such as hot flashes, vaginal dryness, vaginal burning or irritation, or other hormonal changes in the vagina. It is being also for the prevention and treatment of osteoporosis.

Type
Small Molecule
Groups
Approved
Synonyms
  • Esterified estrogens
  • Estrogens, esterified
  • Estrogens, Esterified Component of Menrium
  • Estrogens,esterified
  • Menrium Component Estrogens, Esterified

Pharmacology

Indication

Esterified estrogens are indicated to replace estrogen in women with ovarian failure or other conditions that cause a lack of natural estrogen in the body. It is also indicated for the treatment of symptoms of breast cancer in both men and women. In men it can be used for the treatment of advanced prostate cancer. It is also indicated for the treatment of menopausal symptoms.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Estrogens are responsible for the development and maintenance of the female reproductive system and secondary sexual characteristics. Estradiol is the principle intracellular human estrogen and is more potent than estrone and estriol at the receptor level; it is the primary estrogen secreted prior to menopause.

Mechanism of action

Estrogens modulate the pituitary secretion of gonadotropins, luteinizing hormone, and follicle-stimulating hormone through a negative feedback system; estrogen replacement reduces elevated levels of these hormones.

Absorption

Readily absorbed after oral administration. High concentrations of estrone are achieved with oral administration, whereas higher concentrations of estradiol are generally achieved after percutaneous absorption. Although vaginal products (such as gel, rings, etc.) are administered locally, they achieve high serum concentrations.

Volume of distribution

The distribution of exogenous estrogens is similar to that of endogenous estrogens. Estrogens are widely distributed in the body and are generally found in higher concentration in the sex hormone target organs.

Protein binding

Approximately 95-98% of estradiol is bound loosely to albumin or tightly to sex hormone binding globulin.

Metabolism

Hepatic; partial metabolism via CYP3A4 enzymes; estradiol is reversibly converted to estrone and estriol; oral estradiol also undergoes enterohepatic recirculation by conjugation in the liver, followed by excretion of sulfate and glucuronide conjugates into the bile, then hydrolysis in the intestine and estrogen reabsorption. Sulfate conjugates are the primary form found in postmenopausal women.

Route of elimination

Mainly urinary as estradiol, estrone, estriol, and their glucuronide and sulfate conjugates.

Half-life

Half-life varies, it is in the range 1-2 hr.

Clearance

There is variation in the clearance rate depends on each estrogen individual: estradiol-17β: 580 L/day/m2 estrone: 4050 L/day/m2 estriol: 1110 L/day/m2

Adverse Effects
Adverseeffects
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Toxicity

LD50 IP 325 mg/Kg (rat). LD50 IV 1740 mg/Kg (mouse). LD50 oral >5000 mg/Kg (rat).

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
AbametapirThe serum concentration of Esterified estrogens can be increased when it is combined with Abametapir.
AbciximabEsterified estrogens may decrease the anticoagulant activities of Abciximab.
AbirateroneThe metabolism of Esterified estrogens can be decreased when combined with Abiraterone.
AceclofenacAceclofenac may increase the thrombogenic activities of Esterified estrogens.
AcenocoumarolEsterified estrogens may decrease the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Esterified estrogens.
AdalimumabEsterified estrogens may increase the thrombogenic activities of Adalimumab.
AducanumabEsterified estrogens may increase the thrombogenic activities of Aducanumab.
AlemtuzumabEsterified estrogens may increase the thrombogenic activities of Alemtuzumab.
AlirocumabEsterified estrogens may increase the thrombogenic activities of Alirocumab.
Interactions
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Food Interactions
  • Avoid grapefruit products. Grapefruit inhibits CYP3A metabolism, which may increase the serum concentration of esterified estrogens.
  • Avoid St. John's Wort. This herb induces CYP3A metabolism and may reduce serum levels of esterified estrogens.

Products

Products2
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Product Images
International/Other Brands
Amnestrogen / Estratab / Evex / Femogen
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EstragynTablet0.625 mgOralSearchlight Pharma Inc1974-12-31Not applicableCanada flag
EstragynTablet0.3 mgOralSearchlight Pharma Inc1980-12-31Not applicableCanada flag
Neo Estrone Tab 1.25mgTablet1.25 mgOralNeolab Inc1974-12-312008-04-02Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MenestTablet0.625 mg/1OralPhysicians Total Care, Inc.2008-09-05Not applicableUS flag
MenestTablet, film coated2.5 mg/1OralPfizer Laboratories Div Pfizer Inc2018-09-17Not applicableUS flag
MenestTablet, film coated0.3 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUS flag
MenestTablet0.3 mg/1OralPhysicians Total Care, Inc.2010-12-09Not applicableUS flag
MenestTablet, film coated1.25 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUS flag
MenestTablet1.25 mg/1OralPhysicians Total Care, Inc.2010-12-16Not applicableUS flag
MenestTablet, film coated0.625 mg/1OralAvera McKennan Hospital2015-11-232017-05-24US flag
MenestTablet, film coated0.625 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CovaryxEsterified estrogens (1.25 mg/1) + Methyltestosterone (2.5 mg/1)Tablet, coatedOralCENTRIX PHARMACEUTICAL, INC,2007-04-01Not applicableUS flag11528 0010 01 nlmimage10 5905aced
Covaryx HsEsterified estrogens (0.625 mg/1) + Methyltestosterone (1.25 mg/1)Tablet, coatedOralCENTRIX PHARMACEUTICAL, INC,2007-04-01Not applicableUS flag
EemtEsterified estrogens (1.25 mg/1) + Methyltestosterone (2.5 mg/1)Tablet, coatedOralCREEKWOOD PHARMACEUTICAL, INC,2011-09-01Not applicableUS flag
Eemt H.S.Esterified estrogens (0.625 mg/1) + Methyltestosterone (1.25 mg/1)Tablet, coatedOralPhysicians Total Care, Inc.2006-06-272013-01-15US flag
Eemt HsEsterified estrogens (0.625 mg/1) + Methyltestosterone (1.25 mg/1)Tablet, coatedOralCREEKWOOD PHARMACEUTICAL, INC,2011-09-01Not applicableUS flag
EssianEsterified estrogens (1.25 mg/1) + Methyltestosterone (2.5 mg/1)TabletOralPrasco, Laboratories2005-09-012010-01-31US flag
Essian H.S.Esterified estrogens (0.625 mg/1) + Methyltestosterone (1.25 mg/1)TabletOralPrasco, Laboratories2005-09-012010-01-31US flag
Esterified Estrogen and MethyltestosteroneEsterified estrogens (1.25 mg/1) + Methyltestosterone (2.5 mg/1)TabletOralSeton Pharmaceuticals2021-03-05Not applicableUS flag
Esterified Estrogen and MethyltestosteroneEsterified estrogens (0.625 mg/1) + Methyltestosterone (1.25 mg/1)TabletOralSeton Pharmaceuticals2021-03-05Not applicableUS flag
Esterified Estrogens and MethyltestosteroneEsterified estrogens (1.25 mg/1) + Methyltestosterone (2.5 mg/1)TabletOralbryant ranch prepack2017-08-15Not applicableUS flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
3ASP8Q3768
CAS number
Not Available

References

General References
  1. MSDS [Link]
  2. product info [Link]
  3. product info [Link]
  4. article [Link]
PubChem Substance
347910451
RxNav
214549
Wikipedia
Esterified_estrogens

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHot Flushes, Menopause, Postmenopause1
2CompletedTreatmentMenopause1
2TerminatedTreatmentBreast Cancer1
2TerminatedTreatmentMenopause2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
TabletOral
TabletOral0.3 mg
TabletOral0.625 mg
TabletOral0.3 mg/1
TabletOral0.625 mg/1
TabletOral1.25 mg/1
Tablet, film coatedOral0.3 mg/1
Tablet, film coatedOral0.625 mg/1
Tablet, film coatedOral1.25 mg/1
Tablet, film coatedOral2.5 mg/1
TabletOral1.25 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
Not Available
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

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

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Serine-type endopeptidase inhibitor activity
Specific Function
Major thyroid hormone transport protein in serum.
Gene Name
SERPINA7
Uniprot ID
P05543
Uniprot Name
Thyroxine-binding globulin
Molecular Weight
46324.12 Da
References
  1. CYTOMEL (liothyronine) FDA label [File]

Drug created on November 30, 2015 19:10 / Updated on October 19, 2021 07:39