Estrogens, esterified

Identification

Name
Estrogens, esterified
Accession Number
DB09381
Type
Small Molecule
Groups
Approved
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.

Synonyms
  • Esterified Estrogens
  • Estrogens, Esterified Component of Menrium
  • Estrogens,esterified
  • Menrium Component Estrogens, Esterified
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EstragynTablet0.3 mgOralSearchlight Pharma Inc1980-12-31Not applicableCanada
EstragynTablet0.625 mgOralSearchlight Pharma Inc1974-12-31Not applicableCanada
Neo Estrone Tab 1.25mgTablet1.25 mgOralNeolab Inc1974-12-312008-04-02Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MenestTablet, film coated1.25 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUs
MenestTablet0.3 mg/1OralPhysicians Total Care, Inc.2010-12-09Not applicableUs
MenestTablet1.25 mg/1OralPhysicians Total Care, Inc.2010-12-16Not applicableUs
MenestTablet, film coated0.3 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUs
MenestTablet0.625 mg/1OralPhysicians Total Care, Inc.2008-09-05Not applicableUs
MenestTablet, film coated2.5 mg/1OralPfizer Laboratories Div Pfizer Inc2018-09-17Not applicableUs
MenestTablet, film coated0.625 mg/1OralAvera McKennan Hospital2015-11-232018-06-26Us
MenestTablet, film coated0.625 mg/1OralPfizer Laboratories Div Pfizer Inc1977-09-28Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CovaryxEstrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)Tablet, coatedOralCentrix Pharmaceutical2007-04-01Not applicableUs11528 0010 01 nlmimage10 5905aced
Covaryx HsEstrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)Tablet, coatedOralCentrix Pharmaceutical2007-04-01Not applicableUs
EemtEstrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)Tablet, coatedOralCreekwood Pharmaceuticals, Inc.2011-09-01Not applicableUs
Eemt H.S.Estrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)Tablet, coatedOralPhysicians Total Care, Inc.2006-06-272013-01-15Us
Eemt HsEstrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)Tablet, coatedOralCreekwood Pharmaceuticals, Inc.2011-09-01Not applicableUs
EssianEstrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)TabletOralPrasco, Laboratories2005-09-012010-01-31Us
Essian H.S.Estrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)TabletOralPrasco, Laboratories2005-09-012010-01-31Us
Esterified Estrogens and MethyltestosteroneEstrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)TabletOralANI Pharmaceuticals, Inc.2010-12-22Not applicableUs62559 15020180907 15195 x4ju7f
Esterified Estrogens and MethyltestosteroneEstrogens, esterified (1.25 mg/1) + Methyltestosterone (2.5 mg/1)TabletOralMethod Pharmaceuticals2017-08-15Not applicableUs
Esterified Estrogens and MethyltestosteroneEstrogens, esterified (0.625 mg/1) + Methyltestosterone (1.25 mg/1)TabletOralMethod Pharmaceuticals2017-08-15Not applicableUs
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.

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
DrugInteraction
(R)-warfarinEstrogens, esterified may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinEstrogens, esterified may decrease the anticoagulant activities of (S)-Warfarin.
3,5-diiodothyropropionic acidThe therapeutic efficacy of 3,5-diiodothyropropionic acid can be decreased when used in combination with Estrogens, esterified.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Estrogens, esterified.
5-androstenedioneThe metabolism of Estrogens, esterified can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Estrogens, esterified can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Estrogens, esterified.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Estrogens, esterified.
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Estrogens, esterified.
AbciximabEstrogens, esterified may decrease the anticoagulant activities of Abciximab.
Food Interactions
Not Available

References

General References
  1. MSDS [Link]
  2. product info [Link]
  3. product info [Link]
  4. article [Link]
External Links
PubChem Substance
347910451
Wikipedia
Esterified_estrogens
AHFS Codes
  • 68:16.04 — Estrogens

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHot Flushes, Menopause, Postmenopause1
2CompletedTreatmentMenopause1
2TerminatedTreatmentCancer, Breast1
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

Taxonomy

Classification
Not classified

Enzymes

Kind
Protein
Organism
Human
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

Drug created on November 30, 2015 12:10 / Updated on December 10, 2018 06:10