Estradiol cypionate

The medical uses of estradiol cypionate are the same as those of estradiol and other estrogens. Examples of indications for the drug include hormone therapy and hormonal contraception. In regard to the latter, estradiol cypionate has been used in combination with medroxyprogesterone acetate as a combined injectable contraceptive. Along with estradiol valerate, estradiol undecylate, and estradiol benzoate, estradiol cypionate is used as a form of high-dose estrogen therapy in feminizing hormone therapy for transgender women. The medication has been used to induce puberty in girls with delayed puberty due to hypogonadism. The doses used to induce puberty in girls are 0.2 to 2.5 mg per month, gradually increased over a period of 4 years. The 1 and 3 mg/mL concentrations (containing 5 and 15 mg estradiol cypionate total) have been discontinued in the United States, but the 5 mg/mL concentration (containing 25 mg estradiol cypionate total) remains available. Aside from estradiol cypionate, the only other injectable estrogen formulations that remain available in the United States are estradiol valerate (10 mg/mL, 20 mg/mL, and 40 mg/mL in oil) and conjugated estrogens (25 mg/vial in solution). In addition to single-drug formulations, estradiol cypionate has been marketed in combination with medroxyprogesterone acetate as a microcrystalline aqueous suspension (brand name Lunelle) and in combination with testosterone cypionate as an oil solution (brand name Depo-Testadiol). s of Depo-Estradiol (5 mg/mL estradiol cypionate in cottonseed oil solution for use by intramuscular injection) in the United States. ==Contraindications==

Contraindications of estrogens include coagulation problems, cardiovascular diseases, liver disease, and certain hormone-sensitive cancers such as breast cancer and endometrial cancer, among others. ==Side effects==

The side effects of estradiol cypionate are the same as those of estradiol. Examples of such side effects include breast tenderness and enlargement, nausea, vomiting, bloating, edema, headache, migraine, and melasma. High-dose estrogen therapy with estradiol cypionate injections may also cause an increased risk of thromboembolism, changes in blood lipid profile, increased insulin resistance, and increased levels of prolactin. ==Overdose==

Symptoms of estrogen overdosage may include nausea, vomiting, bloating, increased weight, water retention, breast tenderness, vaginal discharge, heavy legs, and leg cramps. These side effects can be diminished by reducing the estrogen dosage. ==Interactions==

Inhibitors and inducers of cytochrome P450 may influence the metabolism of estradiol and by extension circulating estradiol levels. ==Pharmacology==

, the active form of estradiol cypionate. Pharmacodynamics Estradiol cypionate is an estradiol ester, or a prodrug of estradiol. and estradiol valerate and estradiol cypionate have been found to possess similar affinity for the estrogen receptor. Both estradiol cypionate and estradiol valerate are rapidly cleaved into estradiol in the body, and estradiol valerate has been found to be unable to reach target tissues in any concentration of significance. Because estradiol cypionate is a prodrug of estradiol, it is considered to be a natural and bioidentical form of estrogen. As such, it appears that similarly to depot medroxyprogesterone acetate, combined injectable contraceptives with 5 mg estradiol cypionate and 25 mg medroxyprogesterone acetate have less or no procoagulant effect relative to combined birth control pills. Upon intramuscular injection of estradiol cypionate in an oil solution, the solvent (i.e., oil) is absorbed, and a primary microcrystalline depot is formed within the muscle at the site of injection. With this formulations, estradiol levels peak 2 to 3 days post-injection with average maximal circulating levels of about 250 pg/mL. The elimination half-life of estradiol with these formulations is 8.4 to 10.1 days, and circulating estradiol levels return to a baseline of about 50 pg/mL approximately 14 to 24 days post-injection.{{cite web|url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20874lbl.pdf|archive-url=https://web.archive.org/web/20170210040444/http://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20874lbl.pdf|url-status=dead|archive-date=February 10, 2017|access-date=21 April 2023|website=accessdata.fda.gov Subcutaneous injection Estradiol cypionate in a microcrystalline aqueous suspension has been found to have equivalent effectiveness and virtually identical pharmacokinetics when administered by subcutaneous injection versus intramuscular injection. However, subcutaneous injection is considered to be easier and less painful relative to intramuscular injection, and for these reasons, may result in comparatively greater satisfaction and compliance. ==Chemistry==

Estradiol cypionate is a synthetic estrane steroid and the C17β cyclopentylpropionate (cypionate) fatty acid ester of estradiol. ==History==

Estradiol cypionate was patented by Upjohn in 1952, with a priority date of 1951. Subsequently, it was also marketed in other countries such as European countries and Japan. Along with estradiol valerate (1954) and estradiol benzoate (1933), estradiol cypionate has become one of the most commonly used esters of estradiol. This issue was resolved by switching to a microcrystalline aqueous suspension in the case of estradiol cypionate, allowing it to be combined with medroxyprogesterone acetate in a single suspension. As a result, single-drug preparations of estradiol cypionate are oil solutions, while the combination of estradiol cypionate and medroxyprogesterone acetate are microcrystalline aqueous suspensions. ==Society and culture==

Generic names Estradiol cypionate is the generic name of the drug and its and . Besides the United States, estradiol cypionate has been marketed in France, Germany, Italy, Spain, and Japan, among other countries. Estradiol cypionate is available in Taiwan in combination with testosterone cypionate. Estradiol cypionate/testosterone cypionate and estradiol cypionate/medroxyprogesterone acetate were both formerly marketed in the United States, but have been discontinued in this country. ==See also==