{"ATC Code":"G03CA03","Abbreviation":["E2"],"Adverse Effects":"Adverse effects are generally uncommon; however, there have been reports of the following:","Aliases":["Estradiol","estradiol","β-Estradiol","17β-Estradiol","Oestradiol","Dihydrofolliculin","Estrace","Vivelle","Dihydrotheelin","Dihydroxyestrin","Diogynets","Gynoestryl","Aerodiol","Aquadiol","Climara","Diogyn","Divigel","Gynergon","Vagifem","Dimenformon","Estraderm","Estrogel","Femestral","Evorel","estradiol-17β"],"Biological Half-Life":"The terminal half-lives for various estrogen products post oral or intravenous administration has been reported to range from 1-12 hours. One pharmacokinetic study of oral estradiol valerate administration in postmenopausal women revealed a terminal elimination half-life of 16.9 ± 6.0 h. A pharmacokinetic study of intravenous estradiol administration in postmenopausal women showed an elimination half-life of 27.45 ± 5.65 minutes. The half-life of estradiol appears to vary by route of administration.","Boiling Point":"445.9±45.0","CAS":"50-28-2","ChEBI":"CHEBI:16469","ChEMBL":"CHEMBL135","ChemicalClasses":[],"Chirality":"absolute","Color/Form":"White crystalline powder. Prisms from 80% alcohol","Decomposition":"When heated to decomposition it emits acrid smoke and irritating fumes.","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Estrogens; Hormones","Drug Indication":"Estradiol is indicated in various preparations for the treatment of moderate to severe vasomotor symptoms and vulvar and vaginal atrophy due to menopause, for the treatment of hypoestrogenism due to hypogonadism, castration, or primary ovarian failure, and for the prevention of postmenopausal osteoporosis. It is also used for the treatment of breast cancer (only for palliation therapy) in certain men or women with metastatic disease, and for the treatment of androgen-dependent prostate cancer (only for palliation therapy). It is also used in combination with other hormones as a component of oral contraceptive pills for preventing pregnancy (most commonly as [DB00977], a synthetic form of estradiol).  **A note on duration of treatment**  Recommendations for treatment of menopausal symptoms changed drastically following the release of results and early termination of the Women's Health Initiative (WHI) studies in 2002 as concerns were raised regarding estrogen use. Specifically, the combined estrogen–progestin group was discontinued after about 5 years of follow up due to a statistically significant increase in invasive breast cancer and in cardiovascular events.   Following extensive critique of the WHI results, Hormone Replacement Therapy (HRT) is now recommended to be used only for a short period (for 3-5 years postmenopause) in low doses, and in women without a history of breast cancer or increased risk of cardiovascular or thromboembolic disease. Estrogen for postmenopausal symptoms should always be given with a progestin component due to estrogen's stimulatory effects on the endometrium; in women with an intact uterus, unopposed estrogen has been shown to promote the growth of the endometrium which can lead to endometrial hyperplasia and possibly cancer over the long-term.","Drug Warnings":"ESTROGENS INCREASE THE RISK OF ENDOMETRIAL CANCER- Close clinical surveillance of all women taking estrogens is important. Adequate diagnostic measures, including endometrial sampling when indicated, should be undertaken to rule out malignancy in all cases of undiagnosed persistent or recurring abnormal vaginal bleeding. There is no evidence that the use of \"natural\" estrogens results in a different endometrial risk profile than \"synthetic\" estrogens at equivalent estrogen doses.","EINECS":"200-023-8","Ecotoxicity Values":"EC50; Species: Daphnia magna (Water flea, age \u003c24 hr neonate newly released); Conditions: freshwater, static, 20 °C; Concentration: 1550 ug/L for 24 hr (95% confidence interval: 1050-2040 ug/L); Effect: development, decreased molting /100% purity, 17beta-estradiol/","Erowid Experience Reports":null,"Esters":[],"European Community (EC) Number":"200-023-8","FDA Pharmacological Classification":"4TI98Z838E","Formating":[],"HMDB ID":"HMDB0000151","HeavyAtomCount":20,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Estrogens; Hormones","IUPACName":"(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol","Impurities":["6.beta.-hydroxyestradiol","6.alpha.-hydroxyestradiol","6-ketoestradiol"],"InChI":"InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1","InChIKey":"VOXZDWNPVJITMN-ZBRFXRBCSA-N","Interactions":"Estrogens may interfere with the effects of bromocriptine; dosage adjustment may be necessary. /Estrogens/","MeSH Pharmacological Classification":"Compounds that interact with ESTROGEN RECEPTORS in target tissues to bring about the effects similar to those of ESTRADIOL. Estrogens stimulate the female reproductive organs, and the development of secondary female SEX CHARACTERISTICS. Estrogenic chemicals include natural, synthetic, steroidal, or non-steroidal compounds.","Melting Point":"178.5 °C","MolecularFormula":"C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"272.4 g/mol","Odor":"Odorless","Opticalactivity":"( + )","Pharmacodynamics":"Estradiol acts on the on the estrogen receptors to relieve vasomotor systems (such as hot flashes) and urogenital symptoms (such as vaginal dryness and dyspareunia).  Estradiol has also been shown to exert favorable effects on bone density by inhibiting bone resorption. Estrogen appears to inhibit bone resorption and may have beneficial effects on the plasma lipid profile. Estrogens cause an increase in hepatic synthesis of various proteins, which include sex hormone binding globulin (SHBG), and thyroid-binding globulin (TBG).  Estrogens are known to suppress the formation of follicle-stimulating hormone (FSH) in the anterior pituitary gland.   **A note on hyper-coagulable state, cardiovascular health, and blood pressure**  Estradiol may cause an increased risk of cardiovascular disease, DVT, and stroke, and its use should be avoided in patients at high risk of these conditions.  Estrogen induces a hyper-coagulable state, which is also associated with both estrogen-containing oral contraceptive (OC) use and pregnancy. Although estrogen causes an increase in levels of plasma renin and angiotensin. Estrogen-induced increases in angiotensin, causing sodium retention, which is likely to be the mechanism causing hypertension after oral contraceptive treatment.","Physical Description":"Solid","PubChemId":5757,"Record Description":["LiverTox|Endocrine|Birth control|Estrogen"],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Estradiol","Name":"Estradiol","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00783","Name":"Estradiol","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5757","Name":"Estradiol","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL135","Name":"Estradiol","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16469","Name":"Estradiol","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=50-28-2","Name":"Estradiol","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0000151","Name":"Estradiol","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C00951","Name":"Estradiol","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/4TI98Z838E","Name":"Estradiol","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID0020573","Name":"Estradiol","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 5757, Estradiol. Accessed August 14, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/5757\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/5757\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Estradiol. UNII: 4TI98Z838E. Global Substance Registration System. Accessed August 14, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/4TI98Z838E\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/4TI98Z838E\u003c/a\u003e"],"SMILES":"C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O","SaltData":[{"AcidCount":1,"Amine":"Estradiol","AmineCount":2,"Formula":"O","Name":"hemihydrate","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 144.924 76.417\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h145v77H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"m87.774 24.208.696.073L91.8 9.315l-2.089-.219-2.089-.219z\" 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vasomotor symptoms associated with the menopause. /Included in US product label/","Title":"Estradiol","UNII":"4TI98Z838E","Wikipedia":"Estradiol","XLogP":4}