Esterified estrogens
Pharmaceutical drug From Wikipedia, the free encyclopedia
Esterified estrogens (EEs), sold under the brand names Estratab and Menest among others, is an estrogen medication which is used hormone therapy for menopausal symptoms and low sex hormone levels in women, to treat breast cancer in both women and men, and to treat prostate cancer in men.[2][3][4][5][6] It is formulated alone or in combination with methyltestosterone.[2][3] It is taken by mouth.[1]
Estrone sulfate, the primary active component in esterified estrogens (constitutes about 75 to 85% of total content). | |
 Equilin sulfate, the second most major active component in esterified estrogens (constitutes about 6 to 16% of total content). | |
| Combination of | |
|---|---|
| Sodium estrone sulfate | Estrogen |
| Sodium equilin sulfate | Estrogen |
| Clinical data | |
| Trade names | Estratab, Menest, others |
| Other names | Esterified oestrogens; EEs; Esterified equine estrogens; Esterified equine oestrogens; EEEs |
| Routes of administration | By mouth[1] |
| Drug class | Estrogen |
| ATC code |
|
| Identifiers | |
| PubChem SID | |
| DrugBank | |
| UNII | |
Side effects of EEs include nausea, breast tension, edema, and breakthrough bleeding among others.[7] It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol.[4][2][3] EEs are a prodrug mainly of estradiol and to a lesser extent of equilin.[4]
EEs were introduced for medical use by 1970.[8] They are available in only a few countries, such as Chile and the United States.[2] They have also been marketed in Argentina and Switzerland in the past.[2]
Medical uses
Summarize
Perspective
EEs are used in hormone therapy for menopausal symptoms, female hypogonadism, ovariectomy, and primary ovarian failure and in the treatment of breast cancer and prostate cancer.[3][9]
| Route/form | Estrogen | Low | Standard | High | |||
|---|---|---|---|---|---|---|---|
| Oral | Estradiol | 0.5–1 mg/day | 1–2 mg/day | 2–4 mg/day | |||
| Estradiol valerate | 0.5–1 mg/day | 1–2 mg/day | 2–4 mg/day | ||||
| Estradiol acetate | 0.45–0.9 mg/day | 0.9–1.8 mg/day | 1.8–3.6 mg/day | ||||
| Conjugated estrogens | 0.3–0.45 mg/day | 0.625 mg/day | 0.9–1.25 mg/day | ||||
| Esterified estrogens | 0.3–0.45 mg/day | 0.625 mg/day | 0.9–1.25 mg/day | ||||
| Estropipate | 0.75 mg/day | 1.5 mg/day | 3 mg/day | ||||
| Estriol | 1–2 mg/day | 2–4 mg/day | 4–8 mg/day | ||||
| Ethinylestradiola | 2.5–10 μg/day | 5–20 μg/day | – | ||||
| Nasal spray | Estradiol | 150 μg/day | 300 μg/day | 600 μg/day | |||
| Transdermal patch | Estradiol | 25 μg/dayb | 50 μg/dayb | 100 μg/dayb | |||
| Transdermal gel | Estradiol | 0.5 mg/day | 1–1.5 mg/day | 2–3 mg/day | |||
| Vaginal | Estradiol | 25 μg/day | – | – | |||
| Estriol | 30 μg/day | 0.5 mg 2x/week | 0.5 mg/day | ||||
| IM or SC injection | Estradiol valerate | – | – | 4 mg 1x/4 weeks | |||
| Estradiol cypionate | 1 mg 1x/3–4 weeks | 3 mg 1x/3–4 weeks | 5 mg 1x/3–4 weeks | ||||
| Estradiol benzoate | 0.5 mg 1x/week | 1 mg 1x/week | 1.5 mg 1x/week | ||||
| SC implant | Estradiol | 25 mg 1x/6 months | 50 mg 1x/6 months | 100 mg 1x/6 months | |||
| Footnotes: a = No longer used or recommended, due to health concerns. b = As a single patch applied once or twice per week (worn for 3–4 days or 7 days), depending on the formulation. Note: Dosages are not necessarily equivalent. Sources: See template. | |||||||
Available forms
EEs are available in the form of 0.3 mg, 0.625 mg, 1.25 mg, and 2.5 mg oral tablets.[10] Estratest is a combination formulation of 1.25 mg EEs with 2.5 mg methyltestosterone.[11]
Side effects
Pharmacology
Summarize
Perspective
EEs consist primarily of sodium estrone sulfate and sodium equilin sulfate, and are very similar to conjugated estrogens (CEEs, conjugated equine estrogens; brand name Premarin).[4][6][12][13] However, EEs and CEEs differ in the sources of their contents and in the percentages of their constituents; CEEs consist of approximately 53% sodium estrone sulfate and 25% sodium equilin sulfate, while EEs contain about 75 to 85% sodium estrone sulfate and 6 to 11% sodium equilin sulfate.[4][2][12][14][9] EEs have been found to produce similar serum levels of estrone and estradiol relative to CEEs, although with higher levels of estrone and lower levels of equilin.[4][15] One study found that the risk of venous thrombosis may be less with EEs relative to CEEs.[14][6]
| Estrogen | HF | VE | UCa | FSH | LH | HDL-C | SHBG | CBG | AGT | Liver |
|---|---|---|---|---|---|---|---|---|---|---|
| Estradiol | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 |
| Estrone | ? | ? | ? | 0.3 | 0.3 | ? | ? | ? | ? | ? |
| Estriol | 0.3 | 0.3 | 0.1 | 0.3 | 0.3 | 0.2 | ? | ? | ? | 0.67 |
| Estrone sulfate | ? | 0.9 | 0.9 | 0.8–0.9 | 0.9 | 0.5 | 0.9 | 0.5–0.7 | 1.4–1.5 | 0.56–1.7 |
| Conjugated estrogens | 1.2 | 1.5 | 2.0 | 1.1–1.3 | 1.0 | 1.5 | 3.0–3.2 | 1.3–1.5 | 5.0 | 1.3–4.5 |
| Equilin sulfate | ? | ? | 1.0 | ? | ? | 6.0 | 7.5 | 6.0 | 7.5 | ? |
| Ethinylestradiol | 120 | 150 | 400 | 60–150 | 100 | 400 | 500–600 | 500–600 | 350 | 2.9–5.0 |
| Diethylstilbestrol | ? | ? | ? | 2.9–3.4 | ? | ? | 26–28 | 25–37 | 20 | 5.7–7.5 |
Sources and footnotes
Notes: Values are ratios, with estradiol as standard (i.e., 1.0). Abbreviations: HF = Clinical relief of hot flashes. VE = Increased proliferation of vaginal epithelium. UCa = Decrease in UCa. FSH = Suppression of FSH levels. LH = Suppression of LH levels. HDL-C, SHBG, CBG, and AGT = Increase in the serum levels of these liver proteins. Liver = Ratio of liver estrogenic effects to general/systemic estrogenic effects (hot flashes/gonadotropins). Sources: See template. | ||||||||||
| Compound | RBA to SHBG (%) | Bound to SHBG (%) | Bound to albumin (%) | Total bound (%) | MCR (L/day/m2) |
|---|---|---|---|---|---|
| 17β-Estradiol | 50 | 37 | 61 | 98 | 580 |
| Estrone | 12 | 16 | 80 | 96 | 1050 |
| Estriol | 0.3 | 1 | 91 | 92 | 1110 |
| Estrone sulfate | 0 | 0 | 99 | 99 | 80 |
| 17β-Dihydroequilin | 30 | ? | ? | ? | 1250 |
| Equilin | 8 | 26 | 13 | ? | 2640 |
| 17β-Dihydroequilin sulfate | 0 | ? | ? | ? | 375 |
| Equilin sulfate | 0 | ? | ? | ? | 175 |
| Δ8-Estrone | ? | ? | ? | ? | 1710 |
| Notes: RBA for SHBG (%) is compared to 100% for testosterone. Sources: See template. | |||||
Chemistry
EEs contain synthetic, plant-derived estrogens and are manufactured from soybeans and yams.[5][6]
History
EEs were introduced for medical use by 1970.[8]
Society and culture
Generic names
Estrogens, esterified is the generic name of the drug and its USP.[16] It is also known as esterified estrogens.[3]
Brand names
EEs are marketed under a variety of brand names including Amnestrogen, Estragyn, Estratab, Evex, Femibel, Femogen, Menest, Neo Estrone Tab, and Oestro-Feminal alone, and, in combination with methyltestosterone, under the brand names Covaryx, Delitan, Eemt, Essian, Estratest, Feminova-T, Menogen, and Syntest.[2][5][3]
Availability
EEs are or have been marketed in Argentina, Chile, Switzerland, and the United States.[2] Both EEs and the combination of EEs and methyltestosterone are listed as being marketed only in Chile and the United States as of present.[2]
See also
References
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