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Namespace Prefixes

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Statements

Subject Item
n2:DB00977
rdf:type
n5:Drug
n5:description
A semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally and is often used as the estrogenic component in oral contraceptives [PubChem]. Ethinyl estradiol is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Tri-Cyclen, Triphasil, and Yasmin. The FDA label includes a black box warning that states that combination oral contraceptives should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.
n5:generalReferences
# FDA label.
n5:group
approved
n5:halfLife
36 +/- 13 hours
n5:indication
For treatment of moderate to severe vasomotor symptoms associated with the menopause, female hypogonadism, prostatic carcinoma-palliative therapy of advanced disease, breast cancer, as an oral contraceptive, and as emergency contraceptive.
n5:manufacturer
n12:271B47F6-363D-11E5-9242-09173F13E4C5 n12:271B47F7-363D-11E5-9242-09173F13E4C5 n12:271B47F5-363D-11E5-9242-09173F13E4C5
owl:sameAs
n16:DB00977 n24:DB00977
dcterms:title
Ethinyl Estradiol
adms:identifier
n4:PA449527 n9:C07534 n10:D00554 n11:DB00977 n13:4903 n14:Ethinylestradiol
n5:mechanismOfAction
Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. This cascade is initiated by initially binding to the estrogen receptors. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
n5:packager
n12:271B47E4-363D-11E5-9242-09173F13E4C5 n12:271B47E5-363D-11E5-9242-09173F13E4C5 n12:271B47E8-363D-11E5-9242-09173F13E4C5 n12:271B47E9-363D-11E5-9242-09173F13E4C5 n12:271B47E6-363D-11E5-9242-09173F13E4C5 n12:271B47E7-363D-11E5-9242-09173F13E4C5 n12:271B47EC-363D-11E5-9242-09173F13E4C5 n12:271B47ED-363D-11E5-9242-09173F13E4C5 n12:271B47EA-363D-11E5-9242-09173F13E4C5 n12:271B47EB-363D-11E5-9242-09173F13E4C5 n12:271B47F0-363D-11E5-9242-09173F13E4C5 n12:271B47F1-363D-11E5-9242-09173F13E4C5 n12:271B47EE-363D-11E5-9242-09173F13E4C5 n12:271B47EF-363D-11E5-9242-09173F13E4C5 n12:271B47F4-363D-11E5-9242-09173F13E4C5 n12:271B47F2-363D-11E5-9242-09173F13E4C5 n12:271B47F3-363D-11E5-9242-09173F13E4C5
n5:synonym
Ethynyl estradiol 17 alpha-Ethynylestradiol 17-ethinylestradiol Ethinylestradiolum Etinilestradiol Ethynyloestradiol Ethinyl-Oestranol 17alpha-Ethinyl estradiol 17α-ethynylestradiol 17 alpha-Ethinylestradiol Ethinylestradiol Ethinyloestradiol Ethinylestriol 17-ethinyl-3,17-oestradiol 17-ethinyl-3,17-estradiol Ethynylestradiol 17 alpha-Ethynyloestradiol
n5:toxicity
Oral, mouse LD<sub>50</sub>: 1737 mg/kg. Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females. The FDA label includes a black box warning that states that combination oral contraceptives with ethinyl estradiol should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.
n5:mixture
n17:271B47E3-363D-11E5-9242-09173F13E4C5 n17:271B47E1-363D-11E5-9242-09173F13E4C5 n17:271B47E2-363D-11E5-9242-09173F13E4C5 n17:271B47DF-363D-11E5-9242-09173F13E4C5 n17:271B47E0-363D-11E5-9242-09173F13E4C5 n17:271B47DD-363D-11E5-9242-09173F13E4C5 n17:271B47DE-363D-11E5-9242-09173F13E4C5 n17:271B47DB-363D-11E5-9242-09173F13E4C5 n17:271B47DC-363D-11E5-9242-09173F13E4C5 n17:271B47D9-363D-11E5-9242-09173F13E4C5 n17:271B47DA-363D-11E5-9242-09173F13E4C5 n17:271B47D7-363D-11E5-9242-09173F13E4C5 n17:271B47D8-363D-11E5-9242-09173F13E4C5 n17:271B47D5-363D-11E5-9242-09173F13E4C5 n17:271B47D6-363D-11E5-9242-09173F13E4C5 n17:271B47D3-363D-11E5-9242-09173F13E4C5 n17:271B47D4-363D-11E5-9242-09173F13E4C5 n17:271B47D1-363D-11E5-9242-09173F13E4C5 n17:271B47C8-363D-11E5-9242-09173F13E4C5 n17:271B47D2-363D-11E5-9242-09173F13E4C5 n17:271B47C9-363D-11E5-9242-09173F13E4C5 n17:271B47C6-363D-11E5-9242-09173F13E4C5 n17:271B47D0-363D-11E5-9242-09173F13E4C5 n17:271B47C7-363D-11E5-9242-09173F13E4C5 n17:271B47C4-363D-11E5-9242-09173F13E4C5 n17:271B47C5-363D-11E5-9242-09173F13E4C5 n17:271B47C2-363D-11E5-9242-09173F13E4C5 n17:271B47C3-363D-11E5-9242-09173F13E4C5 n17:271B47C0-363D-11E5-9242-09173F13E4C5 n17:271B47C1-363D-11E5-9242-09173F13E4C5 n17:271B47BE-363D-11E5-9242-09173F13E4C5 n17:271B47BF-363D-11E5-9242-09173F13E4C5 n17:271B47BC-363D-11E5-9242-09173F13E4C5 n17:271B47BD-363D-11E5-9242-09173F13E4C5 n17:271B47BA-363D-11E5-9242-09173F13E4C5 n17:271B47BB-363D-11E5-9242-09173F13E4C5 n17:271B47B8-363D-11E5-9242-09173F13E4C5 n17:271B47B9-363D-11E5-9242-09173F13E4C5 n17:271B47B6-363D-11E5-9242-09173F13E4C5 n17:271B47B7-363D-11E5-9242-09173F13E4C5 n17:271B47B4-363D-11E5-9242-09173F13E4C5 n17:271B47B5-363D-11E5-9242-09173F13E4C5 n17:271B47B2-363D-11E5-9242-09173F13E4C5 n17:271B47B3-363D-11E5-9242-09173F13E4C5 n17:271B47B0-363D-11E5-9242-09173F13E4C5 n17:271B47B1-363D-11E5-9242-09173F13E4C5 n17:271B47AE-363D-11E5-9242-09173F13E4C5 n17:271B47AF-363D-11E5-9242-09173F13E4C5 n17:271B47CE-363D-11E5-9242-09173F13E4C5 n17:271B47CF-363D-11E5-9242-09173F13E4C5 n17:271B47CC-363D-11E5-9242-09173F13E4C5 n17:271B47CD-363D-11E5-9242-09173F13E4C5 n17:271B47CA-363D-11E5-9242-09173F13E4C5 n17:271B47CB-363D-11E5-9242-09173F13E4C5
n5:proteinBinding
97%
n5:synthesisReference
Andreas Sachse, "Method of female hormonal contraception using a fixed extended cycle hormonal preparation containing dienogest and ethinyl estradiol." U.S. Patent US20060079491, issued April 13, 2006.
n7:hasConcept
n8:M0007862
foaf:page
n21:estinyl.htm
n5:IUPAC-Name
n6:271B4800-363D-11E5-9242-09173F13E4C5
n5:InChI
n6:271B4806-363D-11E5-9242-09173F13E4C5
n5:Molecular-Formula
n6:271B4805-363D-11E5-9242-09173F13E4C5
n5:Molecular-Weight
n6:271B4802-363D-11E5-9242-09173F13E4C5
n5:Monoisotopic-Weight
n6:271B4803-363D-11E5-9242-09173F13E4C5
n5:SMILES
n6:271B4804-363D-11E5-9242-09173F13E4C5
n5:Water-Solubility
n6:271B47FE-363D-11E5-9242-09173F13E4C5 n6:271B4816-363D-11E5-9242-09173F13E4C5
n5:logP
n6:271B47FC-363D-11E5-9242-09173F13E4C5 n6:271B47FF-363D-11E5-9242-09173F13E4C5 n6:271B4818-363D-11E5-9242-09173F13E4C5
n5:logS
n6:271B4819-363D-11E5-9242-09173F13E4C5 n6:271B47FD-363D-11E5-9242-09173F13E4C5
n18:hasATCCode
n19:L02AA03 n19:G03CA01
n5:H-Bond-Acceptor-Count
n6:271B480C-363D-11E5-9242-09173F13E4C5
n5:H-Bond-Donor-Count
n6:271B480D-363D-11E5-9242-09173F13E4C5
n5:InChIKey
n6:271B4807-363D-11E5-9242-09173F13E4C5
n5:Polar-Surface-Area--PSA-
n6:271B4808-363D-11E5-9242-09173F13E4C5
n5:Polarizability
n6:271B480A-363D-11E5-9242-09173F13E4C5
n5:Refractivity
n6:271B4809-363D-11E5-9242-09173F13E4C5
n5:Rotatable-Bond-Count
n6:271B480B-363D-11E5-9242-09173F13E4C5
n5:absorption
Rapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).
n5:affectedOrganism
Humans and other mammals
n5:casRegistryNumber
57-63-6
n5:category
n5:containedIn
n22:271B47F9-363D-11E5-9242-09173F13E4C5 n22:271B47FA-363D-11E5-9242-09173F13E4C5 n22:271B47F8-363D-11E5-9242-09173F13E4C5 n22:271B47FB-363D-11E5-9242-09173F13E4C5
n5:Bioavailability
n6:271B4812-363D-11E5-9242-09173F13E4C5
n5:Ghose-Filter
n6:271B4814-363D-11E5-9242-09173F13E4C5
n5:MDDR-Like-Rule
n6:271B4815-363D-11E5-9242-09173F13E4C5
n5:Melting-Point
n6:271B4817-363D-11E5-9242-09173F13E4C5
n5:Number-of-Rings
n6:271B4811-363D-11E5-9242-09173F13E4C5
n5:Physiological-Charge
n6:271B4810-363D-11E5-9242-09173F13E4C5
n5:Rule-of-Five
n6:271B4813-363D-11E5-9242-09173F13E4C5
n5:Traditional-IUPAC-Name
n6:271B4801-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-acidic-
n6:271B480E-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-basic-
n6:271B480F-363D-11E5-9242-09173F13E4C5