Estradiol enantate
Chemical compound / From Wikipedia, the free encyclopedia
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Estradiol enantate (EEn or E2-EN), also spelled estradiol enanthate and sold under the brand names Perlutal and Topasel among others, is an estrogen medication which is used in hormonal birth control for women.[1][2][11] It is formulated in combination with dihydroxyprogesterone acetophenide (DHPA; algestone acetophenide), a progestin, and is used specifically as a combined injectable contraceptive.[1][2] Estradiol enantate is not available for medical use alone.[12][13][14][15] The medication, in combination with DHPA, is given by injection into muscle once a month.[1][2]
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Trade names | Perlutal, Topasel, Unalmes, Yectames, others |
Other names | EEn; E2-EN; EE; E2E; Estradiol enanthate; Estradiol heptanoate; SQ-16150 |
Routes of administration | Intramuscular injection[1][2] |
Drug class | Estrogen; Estrogen ester |
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Bioavailability | IM: High |
Protein binding | Estradiol: ~98% (to albumin and SHBGTooltip sex hormone-binding globulin)[3][4] |
Metabolism | Cleavage via esterases in the liver, blood, and tissues[5][6] |
Metabolites | Estradiol, heptanoic acid, and metabolites of estradiol[5][6] |
Elimination half-life | IM: 5.6–7.5 days[7][1][8][9] |
Duration of action | IM (10 mg): ~20–30 days[10][5] |
Excretion | Urine[1] |
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ECHA InfoCard | 100.023.272 |
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Formula | C25H36O3 |
Molar mass | 384.560 g·mol−1 |
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Side effects of estradiol enantate include breast tenderness, breast enlargement, nausea, headache, and fluid retention.[16] Estradiol enantate is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.[6][5] It is an estrogen ester and a long-lasting prodrug of estradiol in the body.[5][6] Because of this, it is considered to be a natural and bioidentical form of estrogen.[5][17]
Estradiol enantate was first described by 1954,[18] and was first studied in combination with DHPA as a combined injectable contraceptive in 1964.[19][20] The combination was introduced for clinical use by the mid-1970s.[21][22][23] Estradiol enantate is not available as a standalone medication (i.e., by itself without DHPA).[15] The combination is available in Latin America and Hong Kong, and was also previously marketed in Spain and Portugal.[15][2][13]