At more than 1 mg/day,<unk>  is associated with high rates of side effects including nausea, vomiting, abdominal discomfort, headache, and bloating (incidence of 15–50%). Breast changes and feminization The pigmentation of the breast areolae are often very dark and almost black with<unk>  therapy. The pigmentation that occurs with synthetic estrogens such as<unk>  is much greater than with natural estrogens such as estradiol. The mechanism of the difference is unknown. Progestogens like hydroxyprogesterone caproate have been reported to reduce the nipple hyperpigmentation induced by high-dose estrogen therapy. In men treated with it for prostate cancer,<unk>  has been found to produce high rates of gynecomastia (breast development) of 41 to 77%. Blood clots and cardiovascular issues In studies of<unk>  as a form of high-dose estrogen therapy for men with prostate cancer, it has been associated with considerable cardiovascular morbidity and mortality. The risk is dose-dependent. A dosage of 5 mg/day<unk>  has been associated with a 36% increase in non-cancer-related (mostly cardiovascular) deaths. In addition, there is an up to 15% incidence of venous thromboembolism. A 3 mg/day dosage of<unk>  has been associated with an incidence of thromboembolism of 9.6 to 17%, with an incidence of cardiovascular complications of 33.3%. A lower dosage of 1 mg/day<unk>  has been associated with a rate of death due to cardiovascular events of 14.8% (relative to 8.3% for orchiectomy alone). Other long-term effects<unk>  has been linked to a variety of long-term adverse effects, such as increased risk of * vaginal clear-cell adenocarcinoma * vaginal adenosis * T-shaped uterus * uterine fibroids * cervical weakness * breast cancer * infertility * hypogonadism * intersexual gestational defects * depression, * and others, in women who were treated with it during pregnancy, and/or in their offspring. A comprehensive animal study in 1993 found a plethora of adverse effects from<unk>  such as (but not limited to) * genotoxicity (due to quinone metabolite) * teratogenicity * penile and testicular hypoplasia * cryptorchidism (in rats and rhesus monkeys), * liver and renal cancer (in hamsters), ovarian papillary carcinoma (in canines), and * malignant uterine mesothelioma (in squirrel monkeys). Evidence was also found linking ADHD to F2 generations, demonstrating that there is at least some neurological and transgenerational effects in addition to the carcinogenic. Rodent studies reveal female reproductive tract cancers and abnormalities reaching to the F2 generation, and there is evidence of adverse effects such as irregular menstrual cycles intersexual in grandchildren of<unk>  mothers. Additionally, evidence also points to transgenerational effects in F2 sons, such as hypospadias. At this time however, the extent of<unk>  transgenerational effects in humans is not fully understood.
Diethylstilbestrol
Stilbestrol
Polydiethylstilbestrol phosphate
Ethinylestradiol sulfonate
Ethinylestradiol sulfate
Ethinylestradiol
Chloromethylandrostenediol
Estradiol dienantate