(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 ID: 852
• Molecular Formular: C20H24O2
• Molecular Mass: 296.40336
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: 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
• Brand Name: 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
• Synonyms: (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; 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

Database IDs

• CAS Number: 57-63-6
• EC Number: 200-342-2
• MDL Number: MFCD00003690
• Beilstein Number: 2419975
• PubChem SID: 24869989; 24894585; 46508618; 160964315
• PubChem CID: 5991
• CHEBI ID: 4903
• ATC CODE: G03CA01; L02AA03
• CHEMBL: 1078384
• Chemspider ID: 5770
• DrugBank ID: DB00977
• KEGG ID: D00554
• Unique Ingredient Identifier: 423D2T571U
• Wikipedia Title: Ethinyl_estradiol
• Medline Plus: a604032

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.327054
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.8973467
• LogD (pH = 7.4): 3.8968425
• Log P: 3.8973532
• Molar Refractivity: 87.3745 cm^3
• Polarizability: 33.896633 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.63
• LOG S: -4.64
• Solubility (Water): 6.77e-03 g/l

PROPERTIES

Physical Property

• Solubility: 11.3 mg/L; Chloroform; ethanol: soluble50 mg/mL, clear, slightly yellow
• Apperance: White to Off-White Solid
• Melting Point: 180-182°C; 182-183 °C(lit.)
• Optical Rotation: [α]20/D -28°, c = 0.4 in pyridine
• Hydrophobicity(logP): 3.864; 4.3

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: RC8925000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-22
• Safety Statements: 53-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H350
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: 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

Pharmacology Properties

• Admin Routes: Oral, transdermal
• Bioavailability: 97% is bound
• Excretion: Feces and Urine
• Half Life: 36 ± 13 hours
• Metabolism: Liver
• Legal Status: Rx-only (U.S.)
• Pregnancy Category: X (USA)
• Gene Information: rat ... Afp(24177), Esr1(24890), Shbg(24775)
• Mechanism of Action: Estrogen

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); 95%; 97%; 98%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Estrogen; Metabolically active steroid; Oral contraceptive
• Empirical Formula (Hill Notation): C20H24O2

DETAILS

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

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - E685100

A synthetic steroid with high oral estrogenic potency.

REFERENCES

• 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