Ethinyl estradiol |
Last updated: 24/08/2024 |
(Also known as: ethinyl estradiol; EE; aethinyloestradiolum; etinilestradiol; 17alpha-ethinyloestradiol) |
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A prescription drug that is a synthetic oral estrogen | |
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1943, introduced USA | |
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Used to start the heat cycle in horses and to prevent pregnancy in cats and dogs | |
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Dogs; Cats; Horses |
Approval status |
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Not approved | |
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Not approved |
Chemical structure |
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C₂₀H₂₄O₂ | |
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CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O | |
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C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)O | |
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BFPYWIDHMRZLRN-SLHNCBLASA-N | |
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InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1 | |
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Yes |
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Common Name | Relationship | Link |
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ethinyl estradiol hemihydrate | Variant |
General status |
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Contraceptive, Hormone therapy, Medicinal drug | |
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Oestrogen | |
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Semi-synthetic | |
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Diffuses into the target cells and interacts with a protein receptor | |
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[Estrogen receptor, Agonist], [Orphan nuclear receptor PXR, Agonist] | |
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57-63-6 | |
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200-342-2 | |
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Genito urinary system & sex hormones: Sex hormones & modulators of the genital system | |
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QG03CA03 | |
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No | |
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296.40 | |
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19-nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17-diol | |
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(17-α)-19-norpregna-1,3,5(10)-trien-20-yne-3,17,diol | |
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Found in water bodies | |
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Creamy coloured solid |
Formulations |
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4.8 | R3 R = Peer reviewed scientific publications 3 = Unverified data of known source |
Low | ||||||||
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166 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Ethanol3 = Unverified data of known source |
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250 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Ether3 = Unverified data of known source |
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200 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Acetone3 = Unverified data of known source |
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50 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Chloroform3 = Unverified data of known source |
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183 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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Decomposes before boiling | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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1.41 X 1004 | Calculated | - | |||||||
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4.15 | R3 R = Peer reviewed scientific publications 3 = Unverified data of known source |
High | ||||||||
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10.21 | R3 R = Peer reviewed scientific publications 3 = Unverified data of known source |
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87.37 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Degradation |
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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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Soil adsorption and mobility |
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Fate indices |
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Known soil and groundwater metabolites |
None
Other known metabolites |
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2-methoxyethinylestradiol | - | Rat (Liver) | - | ||||
2-hydroxyethinylestradiol-3-methy1 ether | - | Rat (Liver) | - | ||||
2-hydroxyethinylestradiol Note: Main metabolic product in liver |
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Terrestrial ecotoxicology |
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1737 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Rat4 = Verified data |
Moderate | ||||||||
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Aquatic ecotoxicology |
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1.61 | R4 R = Peer reviewed scientific publications Pimephales promelas4 = Verified data |
Moderate | ||||||||
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0.0001 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Danio rerio4 = Verified data |
High | ||||||||
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6.4 | R4 R = Peer reviewed scientific publications Daphnia magna4 = Verified data |
Moderate | ||||||||
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0.84 | R3 R = Peer reviewed scientific publications Unknown species3 = Unverified data of known source |
Moderate | ||||||||
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General |
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Intermediate (class II) | - | - | ||||||||
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1737 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Rat4 = Verified data |
Moderate | ||||||||
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Subcutaneous LD₅₀ > 2000 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intraperitoneal LD₅₀ = 471 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) rat3 = Unverified data of known source |
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Metabolised in the liver and excreted in the faeces, urine and, in small amounts, in milk | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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May cause gastointestinal problems May cause jaundice, hypertension, nasal congestion, headache, dizziness and fluid retention Published studies have demonstrated that enthinyl estradiol can cause cancer at higher dose levels; CLP data - known human carcinogen; US NTP - known carcinogen |
Handling issues |
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May react vigorously with strong oxidizing and reducing agents | |||
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Health: H302, H350, H360, H372 Environment: H410, H411 |
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Not listed (Not listed) | |||
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Not regulated | |||
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ethinyl estradiol | ||
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Aethinyoestradiol | ||
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etinilestradiol | ||
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Record last updated: | 24/08/2024 |
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 |