Synthetic Conjugated Estrogens, B
Identification
- Summary
Synthetic Conjugated Estrogens, B is a mixture of estrogens used to treat a variety of postmenopausal symptoms, including vaginal dryness.
- Brand Names
- Enjuvia
- Generic Name
- Synthetic Conjugated Estrogens, B
- DrugBank Accession Number
- DB09318
- Background
Synthetic conjugated estrogens, B tablets contain a blend of ten synthetic estrogenic substances. The estrogenic substances are: sodium estrone sulfate, sodium equilin sulfate, sodium 17α-dihydroequilin sulfate, sodium 17α-estradiol sulfate, sodium 17β dihydroequilin sulfate, sodium 17α-dihydroequilenin sulfate, sodium 17β-dihydroequilenin sulfate, sodium equilenin sulfate, sodium 17β-estradiol sulfate, and sodium Δ8,9-dehydroestrone sulfate. This blend of ten estrogen derivatives are plant-derived forms of endogenous estrogens and contain many of the same compounds as the Conjugated Equine Estrogens (CEEs), although they are not considered to be equivalent. Available as the product Cenestin (FDA), this combination of plant-derived estrogenic compounds is indicated for the treatment of moderate to severe vasomotor symptoms, vulvovaginal atrophy, vaginal dryness, and paint with intercourse associated with menopause.
All estrogen products mimic the effects of endogenous estrogens in the body which are responsible for the development and maintenance of the female reproductive system and secondary sexual characteristics. Estrogens act by binding to estrogen receptors on a wide variety of tissues in the body and modulating the pituitary secretion of the gonadotropins, luteinizing hormone (LH) and follicle stimulating hormone (FSH) through a negative feedback mechanism. Prior to menopause, the primary source of estrogen is the ovarian follicle, which secretes 70-500 micrograms of estradiol daily, depending on the phase of the menstrual cycle. However, once a woman stops ovulating there is a sharp decline in the production of progesterone and estradiol by the ovaries and a consequent fluctuation in LH and FSH due to a lack of feedback control. This shift in hormone production is largely responsible for many of the symptoms experienced during and after menopause and includes hot flashes and other vasomotor symptoms, painful intercourse, vaginal dryness, and vulvovaginal atrophy. These symptoms are able to be reduced by replacing many of the hormones lost during and following menopause with synthetic or naturally occurring forms, in a therapy known as Hormone Replacement Therapy (HRT).
Pharmacologic estrogen products are available in a variety of formats. Although many of them contain several compounds in common (such as the estrogen derivatives sodium estrone sulfate and sodium equilin sulfate), they vary by their original source (such as horse-, human-, or plant-derived), and the remaining mixture of estrogenic derivatives. Conjugated Equine Estrogens (CEEs) are derived from the urine of pregnant mares and contain a blend of at least 10 estrogen derivatives. Marketed under the brand name Premarin, CEEs are the most frequently used form of conjugated estrogens. There is currently no generic form of CEEs available as a detailed analytical characterization of the active ingredients or of their estrogenic activity is not available at this time. Conjugated estrogens are also available in a plant-derived synthetic form that replicates the naturally occurring, horse-derived forms. Available as either "Synthetic Conjugated Estrogens, A" containing 9 estrogen derivatives (available as Cenestin) or as "Synthetic Conjugated Estrogens, B" containing 10 estrogen derivatives (available as Enjuvia), these products are isolated as precursors from yam or soy plants and then chemically modified to mimic the products available in their naturally occurring form.
- Type
- Small Molecule
- Groups
- Approved
- Synonyms
- Estrogens, Conjugated Synthetic B
- Synthetic Conjugated Estrogens, B
- External IDs
- CE 10
- CE-10
- CE10
Pharmacology
- Indication
For the treatment of moderate to severe vasomotor symptoms due to menopause and for the treatment of moderate to severe vaginal dryness, pain with intercourse, and symptoms of vulvar and vaginal atrophy due to menopause.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Moderate dyspareunia •••••••••••• Management of Moderate vaginal dryness •••••••••••• Management of Moderate vulvovaginal atrophy •••••••••••• Management of Moderate vasomotor symptoms •••••••••••• Management of Severe dyspareunia •••••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Not Available
- Mechanism of action
All estrogen products mimic the effects of endogenous estrogens in the body which are responsible for the development and maintenance of the female reproductive system and secondary sexual characteristics. Estrogens act by binding to estrogen receptors on a wide variety of tissues in the body and modulating the pituitary secretion of the gonadotropins, luteinizing hormone (LH) and follicle stimulating hormone (FSH) through a negative feedback mechanism. Prior to menopause, the primary source of estrogen is the ovarian follicle, which secretes 70-500 micrograms of estradiol daily, depending on the phase of the menstrual cycle. However, once a woman stops ovulating there is a sharp decline in the production of progesterone and estradiol by the ovaries and a consequent fluctuation in LH and FSH due to a lack of feedback control. This shift in hormone production is largely responsible for many of the symptoms experienced during and after menopause and includes hot flashes and other vasomotor symptoms, painful intercourse, vaginal dryness, and vulvovaginal atrophy. These symptoms are able to be reduced by replacing many of the hormones lost during and following menopause with synthetic or naturally occurring forms, in a therapy known as Hormone Replacement Therapy (HRT).
Target Actions Organism AEstrogen receptor alpha ligandHumans - Absorption
Synthetic conjugated estrogens, B are soluble in water and are well absorbed from the gastrointestinal tract after release from the drug formulation. The tablets release synthetic conjugated estrogens, B slowly over a period of several hours.
- 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 concentrations in the sex hormone target organs.
- Protein binding
Estrogens circulate in the blood largely bound to sex hormone binding globulin (SHBG) and albumin.
- Metabolism
Exogenous estrogens are metabolized in the same manner as endogenous estrogens. Circulating estrogens exist in a dynamic equilibrium of metabolic interconversions. These transformations take place mainly in the liver. Estradiol is converted reversibly to estrone, and both can be converted to estriol, which is the major urinary metabolite. Estrogens also undergo enterohepatic recirculation via sulfate and glucuronide conjugation in the liver, biliary secretion of conjugates into the intestine, and hydrolysis in the intestine followed by reabsorption. In postmenopausal women, a significant portion of the circulating estrogens exists as sulfate conjugates, especially estrone sulfate, which serves as a circulating reservoir for the formation of more active estrogens. In vitro and in vivo studies have shown that estrogens are metabolized partially by cytochrome P450 3A4 (CYP3A4).
- Route of elimination
Estradiol, estrone, and estriol are excreted in the urine along with glucuronide and sulfate conjugates.
- Half-life
The half life of baseline-corrected estrone and equilin was found to be 23.46 hr and 15.09 hr, respectively.
- Clearance
Not Available
- Adverse Effects
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- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Synthetic Conjugated Estrogens, B which could result in a higher serum level. Abametapir The serum concentration of Synthetic Conjugated Estrogens, B can be increased when it is combined with Abametapir. Abciximab Synthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Abciximab. Aceclofenac Aceclofenac may increase the thrombogenic activities of Synthetic Conjugated Estrogens, B. Acemetacin Acemetacin may decrease the excretion rate of Synthetic Conjugated Estrogens, B which could result in a higher serum level. - Food Interactions
- Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of synthetic conjugated estrogens, B.
- Avoid St. John's Wort. This herb induces CYP3A4 metabolism and may reduce serum levels of synthetic conjugated estrogens, B.
- Take with or without food.
Products
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- Product Images
- Brand Name Prescription Products
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 8L6LAK9BTR
- CAS number
- 746658-13-9
References
- General References
- Bhamra R, Kaercher U, Oleary CM: Pharmacokinetics of a modified-release estrogen tablet. J Reprod Med. 2010 Sep-Oct;55(9-10):404-10. [Article]
- 14. (2015). In Pharmacology for Women’s Health. Jones & Bartlett Publishers.
- External Links
- KEGG Drug
- D05987
- PubChem Substance
- 347910438
- 618365
- ChEMBL
- CHEMBL1201467
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Conjugated_estrogen
- FDA label
- Download (7.08 MB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Nocturnal Vasomotor Symptoms 1 3 Completed Treatment Menopause 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 0.3 mg/1 Tablet Oral 0.625 mg/1 Tablet Oral 0.9 mg/1 Tablet, film coated Oral 0.3 mg/1 Tablet, film coated Oral 0.45 mg/1 Tablet, film coated Oral 0.625 mg/1 Tablet, film coated Oral 0.9 mg/1 Tablet, film coated Oral 1.25 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6660726 No 2003-12-09 2021-03-08 US US6855703 No 2005-02-15 2021-02-12 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
- Not Available
- Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- 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
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Unknown
- 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 at November 17, 2015 17:11 / Updated at February 21, 2021 18:52