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Ethinylestradiol ( EE ) is an estrogen medication which is used widely in birth control pills in combination with progestins.
The general side effects of EE include breast tenderness and enlargement, headache, fluid retention, and nausea among others.
EE is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol.
EE was developed in the 1930s and was introduced for medical use in 1943.
Contents
1 Medical uses
1.1 Available forms
2 Contraindications
3 Side effects
3.1 Long-term effects
3.1.1 Venous thromboembolism
3.1.2 Cardiovascular toxicity
3.1.3 Cholestatic hepatotoxicity
3.1.4 Endometrial cancer
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.1.1 Antiandrogenic and antigonadotropic effects
6.1.2 Effects on liver protein synthesis
6.1.3 Differences from estradiol
6.2 Pharmacokinetics
6.2.1 Absorption
6.2.2 Distribution
6.2.3 Metabolism
6.2.4 Elimination
7 Chemistry
7.1 Analogues
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Availability
10 References
11 Further reading
Medical uses
There are many uses for EE. It is most commonly used as contraception in combined oral contraceptives (COC), also known as birth control, to prevent pregnancy after sex. EE in its birth control formulation is not only used to prevent pregnancy, but can also be used to treat absence of menstruation, symptoms during menstruation, and acne.
EE is also used as menopausal hormone therapy. The main reason for using HRT in menopausal women is to relieve common vasomotor symptoms such as hot flashes, night sweats, and flushing. Studies have found that estrogen replacement helps improve these symptoms when compared to a placebo.
EE can also be used to treat hypogonadism in women, prevent osteoporosis in women, and has been used as palliative care for prostate cancer in men and breast cancer in women.
EE or any estrogen alone is contraindicated for women who have a uterus due to the increased risk of endometrial cancer ; giving a progestogen with an estrogen mitigates the risk.
Available forms
EE is available in combination with a progestin in a vast number of COCs.
The amount of EE in COCs has reduced over the years.
Contraindications
EE should be avoided in individuals with a history of or known susceptibility to arterial or venous thrombosis ( blood clots ), due to an increased risk of cardiovascular problems such as venous thromboembolism (VTE), myocardial infarction, and ischemic stroke. This includes women with:
History of deep vein thrombosis (DVT) or pulmonary embolism (PE) not receiving anticoagulants
Acute DVT/PE
Prolonged immobilization due to major surgery
Advanced diabetes mellitus with vascular disease
Migraine with aura
Hypertension ≥160/100
Vascular disease
Current and history of ischemic heart disease
Multiple risk factors for atherosclerotic cardiovascular disease (e.g. older age, smoking, diabetes, hypertension, low HDL, high LDL, or high triglyceride levels)
Age ≥35 and smoking ≥15 cigarettes/day
History of cerebrovascular accident
Systemic lupus erythematosus with positive (or unknown) antiphospholipid antibodies
Complicated valvular heart disease
Except when being used to treat it, EE should be avoided in women with current breast cancer due to a possible worsening of prognosis.
EE should also be avoided in breastfeeding women who are less than 21 days postpartum due to an increased risk of VTE.
Due to risk of cholestatic hepatotoxicity, it is widely considered that COCs containing EE should be avoided in women with a history of cholestasis of pregnancy, hepatic tumors, active hepatitis, and familial defects in biliary excretion.
Side effects
Adverse effects of EE-containing COCs
Disease
RR
Cardiovascular diseases (total)
1.5
Myocardial infarction (heart attack) (total)
3.3
Myocardial infarction (non- smokers )
1.0
Myocardial infarction (light smokers )
3.5
Myocardial infarction (heavy smokers )
20.0
Cerebrovascular diseases (total)
1.4
Cerebral thromboses (strokes)
2.5
Subarachnoidal bleeding (heavy smokers )
10.0
Pulmonary embolism
3.0
Deep vein thromboses
2.5
Gall-bladder diseases
3.0
Benign liver tumors
50.0
Hepatocellular carcinoma
3.0
Erythema nodosum et multiforme
3.0
Pruritus (itching)
2.0
Photosensitive eczema
4.0
Irritant agent eczema
2.0
Dermatitis (eczema)
2.0
Chloasma (melasma)
1.5
Cervicitis (6 years of use)
3.0
Chlamydia infections
2.5
Beneficial effects of EE-containing COCs
Disorder or disease
RR
Iron-deficiency anemia
0.58
Menorrhagia
0.52
Irregular menstruation
0.65
Intermenstrual bleeding
0.72
Dysmenorrhea
0.37
Pelvic inflammatory disease (incidence)
0.50
Pelvic inflammatory disease ( hospitalization )
0.22
Trichomonas vaginitis
0.56
Benign breast disease
0.69
Fibrocystic breast disease
0.66
Benign breast fibroadenomas
0.35
Rheumatoid arthritis
0.49
Endometrial cancer
0.40–0.50
Ovarian cancer (incidence)
0.37–0.64
Ovarian cancer (death)
0.20
Benign follicular cysts (high-dose COCs)
0.24
Acne vulgaris
0.44
Low bone mineral density (later in life)
0.35 ( OR )
Ectopic pregnancy
0.19
The severity of side effects can vary based on the dose and administration route of EE. In males, EE has additional side effects, including gynecomastia (breast development), feminization in general, hypogonadism, infertility, and sexual dysfunction (e.g., reduced libido and erectile dysfunction ).
Long-term effects
Venous thromboembolism
VTE is a blood clot in a vein, and includes deep vein thrombosis (VTE) and pulmonary embolism (PE).
The original formulations of COCs contained as much as 150 μg EE.
Cardiovascular toxicity
When used orally at high dosages, for instance as a form of high-dose estrogen therapy in men with prostate cancer and in women with breast cancer, synthetic and non- bioidentical estrogens like EE and diethylstilbestrol are associated with fairly high rates of severe cardiovascular complications such as VTE, myocardial infarction, and stroke.
In contrast to oral synthetic estrogens like EE and diethylstilbestrol, high-dosage polyestradiol phosphate and transdermal estradiol have not been found to increase the risk of cardiovascular mortality or thromboembolism in men with prostate cancer.
Because of its disproportionate effects on liver protein synthesis and associated cardiovascular risks, synthetic estrogens like EE and diethylstilbestrol are no longer used in menopausal hormone therapy.
Cholestatic hepatotoxicity
EE has, albeit rarely (at the low dosages that are now used in COCs), been associated with cholestatic hepatotoxicity similarly to 17α-alkylated androgens / anabolic steroids and 17α-ethynylated 19-nortestosterone progestins.
Endometrial cancer
The high doses of EE that were used in early COCs were associated with a significantly increased risk of endometrial cancer in certain preparations, for instance those containing the progestogen dimethisterone.
Overdose
See also: Estrogen (medication) § Overdose
Estrogens like EE are relatively safe in acute overdose.
Interactions
EE is metabolized by certain cytochrome P450 isoforms, including CYP3A4 and CYP2C9.
Paracetamol (acetaminophen) has been found to competitively inhibit the sulfation of EE, with pretreatment of 1,000 mg of paracetamol significantly increasing the AUC levels of EE (by 22%) and decreasing the AUC levels of ethinylestradiol sulfate (EE sulfate) in women.
In contrast to estradiol, it is unlikely that there is a pharmacokinetic interaction between smoking (which potently induces certain cytochrome P450 enzymes and markedly increases the 2-hydroxylation of estradiol) and EE.
The 19-nortestosterone progestins, gestodene and, to a lesser extent, desogestrel, have been found to inhibit cytochrome P450 enzymes and to progressively inhibit the metabolism and increase the concentrations of EE.
EE has been found to significantly increase (by 38%) the AUC of omeprazole (which is metabolized by CYP2C19 ).
Pharmacology
Pharmacodynamics
EE is an estrogen similarly to natural estrogens like estradiol and conjugated estrogens (Premarin) and synthetic estrogens like diethylstilbestrol. It binds to and activates both isoforms of the estrogen receptor, ERα and ERβ.
Orally, EE is on the order of 100 times as potent by weight as natural estrogens like micronized estradiol and conjugated estrogens, which is largely due to substantially greater resistance to first-pass metabolism.
Relative affinities (%) of ethinylestradiol and related steroids
Compound
PR
AR
ER
GR
MR
SHBG
CBG
Estradiol
2.6
7.9
100
0.6
0.13
8.7–12
<0.1 Ethinylestradiol 15–25 1–3 112 1–3 <1 0.18 <0.1 Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, DHT for SHBG, and cortisol for CBG. Sources: v t e Relative oral potencies of estrogens Estrogen Type HF VE UCa FSH LH HDL - C SHBG CBG AGT Ratio Estradiol Bioidentical 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Estrone Bioidentical ND ND ND 0.3 0.3 ND ND ND ND ND Estriol Bioidentical 0.3 0.3 0.1 0.3 ND 0.2 ND ND ND 0.67 Estrone sulfate Bioidentical ND 0.9 0.9 0.9 0.9 0.5 0.9 0.7 1.5 0.56–1.7 Conjugated estrogens Natural 1.2 1.5 2.0 1.1 1.0 1.5 3.0 1.5 5.0 1.3–4.5 Equilin sulfate Natural ND ND 1.0 ND ND 6.0 7.5 6.0 7.5 ND Ethinylestradiol Synthetic 120 150 400 120 100 400 500 600 350 2.9–5.0 Diethylstilbestrol Synthetic ND ND ND 3.4 ND ND 25.6 24.5 19.5 5.7–7.5 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 hepatic proteins. Ratio = Ratio of liver protein effects to hot flashes relief and gonadotropin suppression. ND = No data. Type: Bioidentical = Identical to those found in humans. Natural = Naturally occurring but not identical to those found in humans (e.g., estrogens of other species). Synthetic = Man-made, does not naturally occur in animals or in the environment. Sources: v t e Oral potencies of estrogens Estrogen Type EPD (mg/14 days) EPD (mg/day) MSD (mg/14 days) MSD (mg/day) Estradiol (micronized) Bioidentical 60 4.3 14–28 1.0–2.0 Estradiol valerate Bioidentical 60 4.3 14–28 1.0–2.0 Estriol Bioidentical 140–150 a 10.0–10.7 a 28–84 2.0–6.0 Estriol succinate Bioidentical 140–150 a 10.0–10.7 a 28–84 2.0–6.0 Conjugated estrogens Natural 60 4.3 8.4–17.5 0.6–1.25 Ethinylestradiol Synthetic 1.0–1.5 0.071–0.11 0.28 0.02 Mestranol Synthetic 1.5–2.0 0.11–0.13 0.35 0.025 Quinestrol Synthetic 2.0–4.0 0.14–0.29 ND ND Diethylstilbestrol Synthetic 20–30 1.4–2.1 ND ND Diethylstilbestrol dipropionate Synthetic 15–20 1.1–1.4 ND ND Dienestrol diacetate Synthetic 40–60 2.9–4.3 ND ND Addendum: The ovulation -inhibiting dose (OID) of ethinylestradiol is 0.1 mg/day. Antiandrogenic and antigonadotropic effects EE is a potent functional antiandrogen in both women and men. Birth control pills containing EE have been found to increase circulating SHBG levels by 2- to 4-fold in women and to reduce free testosterone concentrations by 40 to 80%. Estrogens are antigonadotropins and are able to suppress the secretion of LH and FSH from the pituitary gland and by extension gonadal testosterone production. In addition to its antigonadotropic effects, EE has some anticorticotropic effects, and at high concentrations can significantly suppress androgen production by the adrenal glands. The ovulation-inhibiting dose of EE by itself and not in combination with a progestin is 100 μg/day. Effects on liver protein synthesis EE has marked effects on liver protein synthesis, even at low dosages and regardless of route of administration. A dosage of only 5 µg/day EE has been found to increase SHBG levels by 100% in postmenopausal women, while a dosage of 20 µg/day EE increased them by 200%. A dosage of 10 µg/day EE has been found to increase CBG levels by 50%, while a dosage of 20 µg/day EE increased them by 100%. v t e Proteins and lipids affected by estrogen therapy Proteins, general Coagulation factors Compound Effect Compound Effect α 1 -Antitrypsin + Antithrombin III − Albumin − C-reactive protein + Alkaline phosphatase + Coagulation factor II + Angiotensinogen + Coagulation factor VII + Bilirubin + Coagulation factor VIII + Ceruloplasmin + Coagulation factor IX + Corticosteroid-binding globulin (transcortin) + Coagulation factor X + χ-Glutamyl transpeptidase + Coagulation factor XII + Growth hormone + Fibrinogen + Growth hormone-binding protein + Plasminogen + Insulin-like growth factor 1 − Protein C + Haptoglobin − Prothrombin time − Leucyl aminopeptidase + Lipids α 2 -Microglobulin + Compound Effect Orosomucoid (α 1 -acid glycoprotein) − Apolipoprotein A + Pregnancy zone protein + High-density lipoprotein + Retinol-binding protein + Low-density lipoprotein − Sex hormone-binding globulin + Lecithin + Thyroxine-binding globulin + Total lipids + Transferrin + Triglycerides + Key: + = Increased. − = Decreased. Source: Differences from estradiol Changes in levels of estrogen-sensitive proteins after treatment with oral estradiol or oral ethinylestradiol in postmenopausal women. SHBG levels in men with 1) intramuscular injection of 320 mg polyestradiol phosphate once every 4 weeks alone; 2) the combination of intramuscular injection of 80 mg polyestradiol phosphate once every 4 weeks plus 150 µg/day oral ethinylestradiol; 3) orchiectomy only. EE shows strong and disproportionate effects on liver protein synthesis relative to estradiol. On the other hand, due to the loss of inactivation of EE by 17β-HSD in the endometrium (uterus), EE is relatively more active than estradiol in the endometrium and, for this reason, is associated with a significantly lower incidence of vaginal bleeding and spotting in comparison. EE has been found to have disproportionate effects on liver protein synthesis and VTE risk regardless of whether the route of administration is oral, transdermal, or vaginal, indicating that the use of parenteral routes over the oral route does not result in EE having proportional hepatic actions relative to non-hepatic actions. Comparison of estradiol and ethinylestradiol Parameters Estradiol Ethinylestradiol ER affinity 1 × 10 10 M -1 2–5 × 10 11 M -1 Nuclear retention 6–8 hours 24 hours Blood half-life 90 minutes 7 hours Substrate for 17β-HSD Yes No Bound to SHBG Yes No Relative liver potency 1 ~500–1,500 Relative pituitary potency 1 200 Pharmacokinetics Absorption EE levels while fasting or with a high- fat meal following ingestion of tablets containing a single oral dose of 20 µg EE and 2 mg norethisterone acetate in women. The oral bioavailability of EE is 45% on average, with a wide range of 20% to 74% (though most commonly between 38 and 48%) that is due to high interindividual variability. There may be gender-specific differences in the pharmacokinetics of EE, such that EE may have greater oral potency in women than in men. Distribution The plasma protein binding of EE is 97 to 98%, and it is bound almost exclusively to albumin. Metabolism Due to high first-pass metabolism in the intestines and liver, only 1% of an oral dose of an EE appears in the circulation as EE itself. Aside from sulfate conjugation, EE is mainly metabolized by hydroxylation into catechol estrogens. Unlike the case of estradiol, in which there is a rapid rise in its levels and which remain elevated in a plateau-like curve for many hours, levels of EE fall rapidly after peaking. EE, following oxidative formation of a very reactive metabolite, irreversibly inhibits cytochrome P450 enzymes involved in its metabolism, and this may also play a role in the increased potency of EE relative to estradiol. Elimination EE is eliminated 62% in the feces and 38% in the urine. Chemistry EE, also known as 17α-ethynylestradiol or as 17α-ethynylestra-1,3,5(10)-triene-3,17β-diol, is a synthetic estrane steroid and a derivative of estradiol with an ethynyl substitution at the C17α position. The 17α-ethynylation of estradiol to create EE is analogous to the 17α-substitution of testosterone to make testosterone derivatives such as 17α-ethynylated progestins like ethisterone (17α-ethynyltestosterone) and norethisterone (17α-ethynyl-19-nortestosterone) as well as 17α-alkylated androgens / anabolic steroids like methyltestosterone (17α-methyltestosterone). Analogues See also: List of estrogens § 17α-Substituted estradiol derivatives A number of derivatives of EE exist. History EE was the first orally active synthetic estrogen and was described in 1938 by Hans Herloff Inhoffen and Walter Hohlweg of Schering AG in Berlin. EE was first used in COCs, as an alternative to mestranol, in 1964, and shortly thereafter superseded mestranol in COCs. Society and culture Generic names Ethinylestradiol is the English generic name of the drug and its INN, USAN, BAN, and JAN. The name of the drug is often abbreviated as EE or as EE2 in the medical literature. Brand names EE has been marketed as a standalone oral drug under the brand names Esteed, Estinyl, Feminone, Lynoral, Menolyn, Novestrol, Palonyl, Spanestrin, and Ylestrol among others, although most or all of these formulations are now discontinued. Availability EE is marketed widely throughout the world.

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