Esterified estrogens

Identification

Name
Esterified estrogens
Accession Number
DB09381
Description

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.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
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Toxicity

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

Affected organisms
Not Available
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.
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.
Acetylsalicylic acidEsterified estrogens may decrease the anticoagulant activities of Acetylsalicylic acid.
AdalimumabEsterified estrogens may increase the thrombogenic activities of Adalimumab.
AlemtuzumabEsterified estrogens may increase the thrombogenic activities of Alemtuzumab.
AlirocumabEsterified estrogens may increase the thrombogenic activities of Alirocumab.
AllantoinThe therapeutic efficacy of Allantoin can be decreased when used in combination with Esterified estrogens.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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

Product Images
International/Other Brands
Amnestrogen / Estratab / Evex / Femogen
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EstragynTabletOralSearchlight Pharma Inc1980-12-31Not applicableCanada flag
EstragynTabletOralSearchlight Pharma Inc1974-12-31Not applicableCanada flag
Neo Estrone Tab 1.25mgTabletOralNeolab Inc1974-12-312008-04-02Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MenestTablet, film coated0.625 mg/1OralAvera McKennan Hospital2015-11-232017-05-24US flag
MenestTablet, film coated0.3 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUS flag
MenestTablet, film coated0.625 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUS flag
MenestTablet0.3 mg/1OralPhysicians Total Care, Inc.2010-12-09Not applicableUS flag
MenestTablet, film coated2.5 mg/1OralPfizer Laboratories Div Pfizer Inc2018-09-17Not applicableUS flag
MenestTablet1.25 mg/1OralPhysicians Total Care, Inc.2010-12-16Not applicableUS flag
MenestTablet, film coated1.25 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUS flag
MenestTablet0.625 mg/1OralPhysicians Total Care, Inc.2008-09-05Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
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 Estrogens and MethyltestosteroneEsterified estrogens (1.25 mg/1) + Methyltestosterone (2.5 mg/1)TabletOralANIP Acquisition Company2010-12-222010-12-10US flag
Esterified Estrogens and MethyltestosteroneEsterified estrogens (1.25 mg/1) + Methyltestosterone (2.5 mg/1)TabletOralMethod Pharmaceuticals, LLC2017-08-15Not applicableUS flag
Esterified Estrogens and MethyltestosteroneEsterified estrogens (0.625 mg/1) + Methyltestosterone (1.25 mg/1)TabletOralANI Pharmaceuticals, Inc.2010-12-22Not applicableUS flag62559 15020180907 15195 x4ju7f

Categories

Drug Categories
Classification
Not classified

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
AHFS Codes
  • 68:16.04 — 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/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
TabletOral
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 12:10 / Updated on September 22, 2020 02:11

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