Estradiol cyprionate |
![]() Last updated: 16/09/2025 |
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(Also known as: depoestradiol) |
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A semisynthetic estrogenic hormone with veterinary applications | |
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Mainly used as a hormone replacement therapy in conditions of inadequate estrogen production | |
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Horses; Cattle; Cats; Dogs |
Approval status |
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Not approved | |
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Not approved |
Chemical structure |
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Estradiol exhibits stereoisomerism, primarily due to the configuration of its hydroxyl groups and the orientation of its steroid backbone. The most biologically active form is 17beta-estradiol, where the hydroxyl group at carbon 17 is in the beta position. Its stereoisomer, 17alpha-estradiol, has the hydroxyl group in the alpha position and is significantly less potent in estrogenic activity. Additionally, estradiol can undergo glucuronidation at either the 3-hydroxyl or 17-hydroxyl positions, forming estradiol-3-glucuronide and estradiol-17-glucuronide, which are regioisomers with distinct metabolic pathways and biological roles. The cypionate ester is attached at the 17beta-hydroxyl group but not introduce additional isomerism. | |
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C₂₆H₃₆O₃ | |
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CC12CCC3C(C1CCC2OC(=O)CCC4CCCC4)CCC5=C3C=CC(=C5)O | |
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C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=C3C=CC(=C5)O | |
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UOACKFBJUYNSLK-XRKIENNPSA-N | |
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InChI=1S/C26H36O3/c1-26-15-14-21-20-10-8-19(27)16-18(20)7-9-22(21)23(26)11-12-24(26)29-25(28)13-6-17-4-2-3-5-17/h8,10,16-17,21-24,27H,2-7,9,11-15H2,1H3/t21-,22-,23+,24+,26+/m1/s1 | |
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Yes |
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Common Name | Relationship | Link |
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estradiol | Parent | ![]() |
General status |
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Steroid hormone | |
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Semi-synthetic | |
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Substance binds to its specific intracellular receptor and regulates DNA transcription for protein formation | |
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[Estrogen receptor alpha, Agonist], [Estrogen receptor beta, Agonist], [Beclin-1, Binder], [ATP synthase subunit a, Inhibitor], [Nuclear receptor subfamily 1 group I member 2, Binder], [Neuronal acetylcholine receptor subunit alpha-4, Binder], [G-protein coupled estrogen receptor 1, Binder] | |
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313-06-4 | |
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206-237-8 | |
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9403 | |
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Estrogens: Natural and semisynthetic estrogens, plain | |
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QG03CA03 | |
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No | |
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396.6 | |
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[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate | |
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17-β-Estradiol 17-cyclopentylpropionate | |
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Commercial |
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Current | |||
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1929, first isolated; 1930s, clinical use began; 1950s, veterinary adoption | |||
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Often supplied as a a sterile injectable solution | |||
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The production of estradiol cypionate begins with estradiol which undergoes esterification at the 17beta-hydroxyl group using cyclopentylpropionic acid or its activated derivative, such as cyclopentylpropionyl chloride. This reaction typically takes place in an organic solvent like pyridine or methanol, often in the presence of a base such as potassium carbonate, which facilitates the formation of the ester bond. The mixture is stirred under controlled temperature conditions to ensure complete reaction, after which the product is precipitated, filtered, and washed to remove impurities. The crude compound is then purified through recrystallisation, often using a solvent system like methanol or benzene-petroleum ether, to yield high-purity estradiol cypionate. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Known metabolites |
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General |
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Eliminated from the body through a two-step process involving enzymatic hydrolysis followed by hepatic metabolism and renal excretion | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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IARC: known carcinogen; CLP data: known human carcinogen; NTP data: carcinogen |
Handling issues |
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estradiol cyprionate | ||
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Record last updated: | 16/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |