CAS 57-63-6|Nogest-S|Progynon M|Dicromil|EE|Ginestrene|Kolpolyn|Ethinyloestradiol|Oviol|Ethidol|Etistradiol|Menolyn|Progynon C|Marvelon|Follicoral|Inestra|Anovlar|Ethinylestriol|Estoral|Ylestrol|Dip...

General Information

Structure

Molecular Formula

C₂₀H₂₄O₂

Molecular Mass

296.40336

Exact Mass

296.17763001

Charge

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

Canonic Smiles

C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O

Isomeric Smiles

O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(O)cc2)CC1)C)C#C

Calculated Properties

JChem

LogD (pH = 7.4)

3.90

LogD (pH = 5.5)

3.90

Log P

3.90

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

10.33

Polar Surface Area

40.46

Polarizability

34.52

Molar Refractivity

87.37

LOG S

-4.83

Data Source

Names and Identifiers

Brand Name

Nogest-SProgynon MDicromilGinestreneKolpolynOviolEthidolEtistradiolMenolynProgynon CMarvelonFollicoralInestraAnovlarEstoralYlestrolDiprolDiognat-ELinoralEtinestrolOrestralynEsteedErtonylEthy 11OrestraylnPrimogyn MDiogyn ENovestrolAmenoronEticyclolEstopherolHalodrinPrimogyn CCyclosaDyloformProsexolEtinoestrylEticylolAmenoroneEthinoralEtivexEtinestrylMercilonPrimogynVarnolineNeo-EstroneEstoralsOradiolGynolettEticyclinEston-EDiogyn-EEstigynSpanestrinOrtho-CyclenMicrofollin

Synonyms

EEEthinyloestradiolEthinylestriolEthynyloestradiolEthynylestradiol17 alpha-EthynyloestradiolEthinyl EstradiolEthinyl-Oestranol17 alpha-EthynylestradiolEthynyl estradiolAethinyloestradiolumEOEtinilestradiol [INN-Spanish]17 alpha-EthinylestradiolEthinylestradiolum [INN-Latin]Aethinyoestradiol [German]17α-乙炔基-1,3,5(10)-雌甾三烯-1,17β-二醇17α-乙炔基雌二醇17α-Ethynylestradiol19-去甲-1,3,5(10),17α-雌甾三烯-20-炔-3,17-二醇炔雌醇Ethinylestradiol19-Nor-1,3,5(10),17α-pregnatrien-20-yne-3,17-diolEthynyl EstradiolAmenoronEticyclin17α-Ethynyl-1,3,5(10)-estratriene-3,17β-diolLynoral, Oradiol17α-EthynylestradiolKolpolynFeminoneOrestralynGynolett(17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diolEticylolEtivexPrimogyn CEstigynTuristeronLynoralEtifollin(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-diolEticyclolEthinylestradiolTriquilarEstinylProgynon C17-ethinyl-3,17-estradiolEthinyl estradiol17alpha-ethynylestradiol17-ethinylestradiolEthinylestradiol17alpha-ethynylestradiol17alpha-Ethinyl estradiol17-ethinyl-3,17-oestradiolethinyloestradiolEthynyl estradiol

IUPAC name

(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 (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 (1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol (1R,3aS,3bR,9bS,11aS)-1-ethynyl-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol

IUPAC Traditional name

ethinyl estradiol (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

API Name

Ethinyl Estradiol

Names and Identifiers

Registration numbers

PubChem CID

EC Number

CAS Number

Beilstein Number

MDL Number

PubChem SID

46508618160964315248945852486998911533305

KEGG ID

DrugBank ID

Medline Plus

CHEMBL

ATC CODE

Wikipedia Title

Unique Ingredient Identifier

423D2T571U

Chemspider ID

5770

CHEBI ID

4903CHEBI:4903

BRENDA Ligand Database

8464907121058678912525919971150393269126091160334889114774

UniProt Database

Q5AH87Q06278P22309B7ZS96P49888

BKMS React Database

93269115038464126096789116033488910581147741252591997

MetaboLights Database

MTBLS2145MTBLS4099MTBLS2457MTBLS2871MTBLS1918MTBLS1693

SABIO-RK Database

139921186010324114901482479111399413888

Rhea Database

RHEA:51228

Patent number

WO2005082908EP1842521EP1640009EP1598069US2008051463WO2006098961US2004072813EP1342814EP1938798WO2006060142US2006030555

BRENDA Database

1.1.1.511.1.1.502.8.2.11.1.1.1451.3.1.222.8.2.152.3.1.371.11.1.72.8.2.22.4.1.172.8.2.41.2.3.11.14.14.1

KEGG DRUG Database

D00554

ArrayExpress (Gene Expression Altlas)

E-TABM-12E-TABM-105

PubMed Citation Links

20189629

NURSA Database

10.1621/rRFmLctKAu10.1621/qEadXanwpb10.1621/AEvCJpyNNb10.1621/XwobySFqSi10.1621/ox3Q9qjyWd10.1621/lEnP5n4dC810.1621/XQSiXZluFZ

VSDB Database

1,887

SureChEMBL Database

SCHEMBL4071

HMDB Database

HMDB0001926

Drug Central Database

1,082

GeneOntology Database

ACToR Database

Protein Data Bank

LIPID MAPS Instance

CompTox Database

LINCS Database

ArrayExpress (Repository of Microarray data)

E-TOXM-20

Reaxys Registry

2419975

Registration numbers

Properties

Physical Property

Safety Information

-20°C

-20°C Freezer

45-22

53-36/37/39-45

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Wikipedia

Ethinyl_estradiol

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

02463

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

46263

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

TRC

E685100

A synthetic steroid with high oral estrogenic potency.

ChEBI

CHEBI:4903

A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

• 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)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 590C, (nmr)

• Inhoffen, H.H. et al., Ber., 1938, 71, 1024, (synth)

• Tacey, R.L. et al., J. Pharm. Biomed. Anal., 1994, 12, 1303, (hplc)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1445

• Ercoli, A. et al., Chem. Ind. (London), 1961, 1037, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5766

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EEH500; QFA250

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity