(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,14-diol

• ChemBase编号: 852
• 分子式: C20H24O2
• 平均质量: 296.40336
• 单一同位素质量: 296.17763001
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(O)cc2)CC1)C)C#C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
• InChI: 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
• InChIKey: BFPYWIDHMRZLRN-SLHNCBLASA-N

名称和登记号

名称

• IUPAC标准名: (1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,14-diol; (1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,14-diol; (1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol; (1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol
• IUPAC传统名: ethinyl estradiol; (1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,14-diol
• 商标名: Amenoron; Amenorone; Anovlar; Cyclosa; Dicromil; Diognat-E; Diogyn E; Diogyn-E; Diprol; Dyloform; Ertonyl; Esteed; Estigyn; Eston-E; Estopherol; Estoral; Estorals; Ethidol; Ethinoral; Ethy 11; Eticyclin; Eticyclol; Eticylol; Etinestrol; Etinestryl; Etinoestryl; Etistradiol; Etivex; Follicoral; Ginestrene; Gynolett; Halodrin; Inestra; Kolpolyn; Linoral; Marvelon; Menolyn; Mercilon; Microfollin; Neo-Estrone; Nogest-S; Novestrol; Oradiol; Orestralyn; Orestrayln; Ortho-Cyclen; Oviol; Primogyn; Primogyn C; Primogyn M; Progynon C; Progynon M; Prosexol; Spanestrin; Varnoline; Ylestrol
• 别名: 17α-乙炔基-1,3,5(10)-雌甾三烯-1,17β-二醇; 19-去甲-1,3,5(10),17α-雌甾三烯-20-炔-3,17-二醇; 炔雌醇; 17α-乙炔基雌二醇; (17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol; 17α-Ethynylestradiol; Amenoron; Eticylol; Eticyclin; Etivex; Feminone; Gynolett; Kolpolyn; Lynoral, Oradiol; Orestralyn; Primogyn C; Ethynyl Estradiol; 17α-Ethynylestradiol; 17α-Ethynyl-1,3,5(10)-estratriene-3,17β-diol; 19-Nor-1,3,5(10),17α-pregnatrien-20-yne-3,17-diol; Ethinylestradiol; Ethinylestradiolum [INN-Latin]; Ethinyl-Oestranol; Ethinylestriol; Ethinyloestradiol; Ethynylestradiol; Ethynyloestradiol; Etinilestradiol [INN-Spanish]; EE; EO; Aethinyoestradiol [German]; 17 alpha-Ethinylestradiol; Aethinyloestradiolum; 17 alpha-Ethynyloestradiol; 17 alpha-Ethynylestradiol; Ethynyl estradiol; Ethinyl Estradiol; Estigyn; Estinyl; Eticyclol; Etifollin; Lynoral; Progynon C; Triquilar; Turisteron; Ethinylestradiol; (1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

登记号

• CAS号: 57-63-6
• EC号: 200-342-2
• MDL号: MFCD00003690
• Beilstein号: 2419975
• PubChem SID: 24869989; 24894585; 160964315; 46508618
• PubChem CID: 5991
• CHEBI ID: 4903
• ATC码: G03CA01; L02AA03
• CHEMBL: 1078384
• Chemspider ID: 5770
• DrugBank ID: DB00977
• KEGG ID: D00554
• 美国药典/FDA物质标识码: 423D2T571U
• 维基百科标题: Ethinyl_estradiol
• Medline Plus: a604032

理论计算性质

JChem

• Acid pKa: 10.327054
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 3.8973467
• LogD (pH = 7.4): 3.8968425
• Log P: 3.8973532
• 摩尔折射率: 87.3745 cm^3
• 极化性: 33.896633 Å^3
• 极化表面积: 40.46 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.63
• LOG S: -4.64
• 溶解度: 6.77e-03 g/l

分子性质

理化性质

• 溶解度: 11.3 mg/L; Chloroform; ethanol: soluble50 mg/mL, clear, slightly yellow
• 外观: White to Off-White Solid
• 熔点: 180-182°C; 182-183 °C(lit.)
• 比旋光度: [α]20/D -28°, c = 0.4 in pyridine
• 疏水性(logP): 3.864; 4.3

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: RC8925000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 45-22
• 安全公开号: 53-36/37/39-45
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H350
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

药理学性质

• 给药途径: Oral, transdermal
• 生物利用度: 97% is bound
• 排泄: Feces and Urine
• 半衰期: 36 ± 13 hours
• 代谢: Liver
• 法定药品分级: Rx-only (U.S.)
• 妊娠期药物分类: X (USA)
• 相关基因信息: rat ... Afp(24177), Esr1(24890), Shbg(24775)
• 生物活性机理: Estrogen

产品相关信息

• 纯度: ≥98%; ≥98.0% (HPLC); 95%; 97%; 98%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 应用领域: Estrogen; Metabolically active steroid; Oral contraceptive
• Empirical Formula (Hill Notation): C20H24O2

详细说明

DrugBank - DB00977

• Drug Groups: approved
• 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]
• 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.
• Pharmacology: Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol. It is one of two estrogens currently used in oral contraceptive pills. The other, mestranol, is converted to ethinyl estradiol before it is biologically active. Ethinyl estradiol and norethindrone are used together as an oral contraceptive agent.
• Toxicity: Oral, mouse LD₅₀: 1737 mg/kg. Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.
• Absorption: Rapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).
• Half Life: 36 +/- 13 hours
• Protein Binding: 97%
• External Links: Wikipedia; RxList

Selleck Chemicals - S1625

Research Area: Endocrinology
Biological Activity:
Ethynyl estradiol is an orally bio-active estrogen used in almost all modern formulations of combined oral contraceptive pills. EE is hormonally effective by activating the estrogen receptor and thus is an estrogen. It finds its most common use in the estrogen-progestin combination preparations of oral contraceptives. [1][2]

Sigma Aldrich - E4876

Biochem/physiol Actions
17α-Ethynylestradiol is an orally bio-active synthetic estrogen used as an oral contraceptive.
包装
1, 10 g in glass bottle
100 mg in glass bottle

Sigma Aldrich - 02463

Other Notes
Affects lipoprotein lipase and hepatic lipase activities, consequently used in studies of VLDL metabolism1

Sigma Aldrich - 46263

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - E685100

A synthetic steroid with high oral estrogenic potency.

参考文献

• http://en.wikipedia.org/wiki/Ethinylestradiol
• Koetsawang, S., et al: Contraception, 25, 231 (1982)
• Cuttler, L., et al.: J. Clin. Endocrinol. Metab., 60, 1087 (1982)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 590C, (nmr)
• Inhoffen, H.H. et al., Ber., 1938, 71, 1024, (synth)
• Ercoli, A. et al., Chem. Ind. (London), 1961, 1037, (synth)
• Counsell, R.E. et al., J. Med. Chem., 1966, 9, 689, (pharmacol)
• Vaalburg, W. et al., J. Labelled Compd. Radiopharm., 1977, 13, 200, (synth)
• Ranney, R.E. et al., J. Toxicol. Environ. Health, 1977, 3, 139; 231, (revs, metab)
• Horvath, G. et al., Adv. Mass Spectrom., 1978, 7B, 1280, (ms)
• Newburger, J. et al., Contraception, 1985, 32, 33, (rev, pharmacol)
• Duesterberg, B. et al., Arzneim.-Forsch., 1986, 36, 1187, (pharmacol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5766
• Tacey, R.L. et al., J. Pharm. Biomed. Anal., 1994, 12, 1303, (hplc)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1445
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EEH500; QFA250