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.

Synonyms

Esterified Estrogens
Estrogens, Esterified Component of Menrium
Estrogens,esterified
Menrium Component Estrogens, Esterified

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Estragyn	Tablet	0.625 mg	Oral	Searchlight Pharma Inc	1974-12-31	Not applicable
Estragyn	Tablet	0.3 mg	Oral	Searchlight Pharma Inc	1980-12-31	Not applicable
Neo Estrone Tab 1.25mg	Tablet	1.25 mg	Oral	Neolab Inc	1974-12-31	2008-04-02

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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

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

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Menest	Tablet, film coated	1.25 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1977-09-28	Not applicable
Menest	Tablet	0.625 mg/1	Oral	Physicians Total Care, Inc.	2008-09-05	Not applicable
Menest	Tablet, film coated	0.625 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1977-09-28	Not applicable
Menest	Tablet, film coated	0.3 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	1977-09-28	Not applicable
Menest	Tablet	0.3 mg/1	Oral	Physicians Total Care, Inc.	2010-12-09	Not applicable
Menest	Tablet, film coated	0.625 mg/1	Oral	Avera McKennan Hospital	2015-11-23	2018-06-26
Menest	Tablet, film coated	2.5 mg/1	Oral	Pfizer Laboratories Div Pfizer Inc	2018-09-17	Not applicable
Menest	Tablet	1.25 mg/1	Oral	Physicians Total Care, Inc.	2010-12-16	Not applicable

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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

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

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Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Covaryx	Estrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)	Tablet, coated	Oral	Centrix Pharmaceutical	2007-04-01	Not applicable
Covaryx Hs	Estrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)	Tablet, coated	Oral	Centrix Pharmaceutical	2007-04-01	Not applicable
Eemt	Estrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)	Tablet, coated	Oral	Creekwood Pharmaceuticals, Inc.	2011-09-01	Not applicable
Eemt H.S.	Estrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)	Tablet, coated	Oral	Physicians Total Care, Inc.	2006-06-27	2013-01-15
Eemt Hs	Estrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)	Tablet, coated	Oral	Creekwood Pharmaceuticals, Inc.	2011-09-01	Not applicable
Essian	Estrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)	Tablet	Oral	Prasco, Laboratories	2005-09-01	2010-01-31
Essian H.S.	Estrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)	Tablet	Oral	Prasco, Laboratories	2005-09-01	2010-01-31
Esterified Estrogens and Methyltestosterone	Estrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)	Tablet	Oral	ANIP Acquisition Company	2010-12-22	2010-12-10
Esterified Estrogens and Methyltestosterone	Estrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)	Tablet	Oral	ANI Pharmaceuticals, Inc.	2010-12-22	Not applicable
Esterified Estrogens and Methyltestosterone	Estrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)	Tablet	Oral	Method Pharmaceuticals	2017-08-15	Not applicable

International/Other Brands

Amnestrogen / Estratab / Evex / Femogen

Categories

UNII

3ASP8Q3768

CAS number

Not Available

Weight

Not Available

Chemical Formula

Not Available

InChI Key

Not Available

InChI

Not Available

IUPAC Name

Not Available

SMILES

Not Available

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

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.

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Adverse Effects

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

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

Drug	Interaction
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4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be decreased when combined with Estrogens, esterified.
5-androstenedione	The metabolism of Estrogens, esterified can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide B	The metabolism of Estrogens, esterified can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanine	The metabolism of 6-O-benzylguanine can be decreased when combined with Estrogens, esterified.
7-ethyl-10-hydroxycamptothecin	The metabolism of Estrogens, esterified can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecin	The metabolism of 9-aminocamptothecin can be decreased when combined with Estrogens, esterified.
Abatacept	The metabolism of Estrogens, esterified can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Estrogens, esterified.
Abiraterone	The metabolism of Estrogens, esterified can be decreased when combined with Abiraterone.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Estrogens, esterified.

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Extended Description

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

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Severity

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Evidence Level

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Action

Evidence Level

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Food Interactions

Not Available

References

General References

MSDS [Link]
product info [Link]
product info [Link]
article [Link]

External Links

PubChem Substance: 347910451
Wikipedia: Esterified_estrogens

AHFS Codes

68:16.04 — Estrogens

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Completed	Treatment	Hot Flushes, Menopause, Postmenopause	1
2	Completed	Treatment	Menopause	1
2	Terminated	Treatment	Cancer, Breast	1
2	Terminated	Treatment	Menopause	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Tablet, coated	Oral
Tablet	Oral
Tablet	Oral	0.3 mg
Tablet	Oral	0.625 mg
Tablet	Oral	0.3 mg/1
Tablet	Oral	0.625 mg/1
Tablet	Oral	1.25 mg/1
Tablet, film coated	Oral	0.3 mg/1
Tablet, film coated	Oral	0.625 mg/1
Tablet, film coated	Oral	1.25 mg/1
Tablet, film coated	Oral	2.5 mg/1
Tablet	Oral	1.25 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

Taxonomy

Classification: Not classified

Enzymes

Details1. Cytochrome P450 3A4

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

Details1. Thyroxine-binding globulin

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

CYTOMEL (liothyronine) FDA label [File]

Drug created on November 30, 2015 12:10 / Updated on May 21, 2019 12:26