CAS 57-63-6|Amenoron|Ethinyl Estradiol|Neo-Estrone|Oradiol|(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|Ethynylestradiol|Etivex|Hal...

基本信息

化学结构

分子式

C₂₀H₂₄O₂

分子量

296.40336

精确质量

296.17763001

电荷

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

计算属性

JChem

LogD (pH = 7.4)

3.90

LogD (pH = 5.5)

3.90

Log P

3.90

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

10.33

极化表面积

40.46

极化性

34.52

摩尔折射率

87.37

LOG S

-4.83

数据来源

名称和标识

商标名

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

别名

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标准名

(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传统名

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名称

Ethinyl Estradiol

名称和标识

数据登录号

PubChem CID

Beilstein号

EC号

CAS号

MDL号

PubChem SID

46508618160964315248945852486998911533305

KEGG ID

Medline Plus

DrugBank ID

CHEMBL

美国药典/FDA物质标识码

维基百科标题

ATC码

CHEBI ID

Chemspider ID

Rhea数据库

专利号

EP1640009EP1842521EP1598069WO2005082908WO2006098961US2008051463EP1938798EP1342814US2004072813WO2006060142US2006030555

MetaboLights数据库

MTBLS2145MTBLS4099MTBLS2871MTBLS2457MTBLS1693MTBLS1918

SABIO-RK数据库

139921186014824114901032413994791113888

BRENDA数据库

1.1.1.501.1.1.511.3.1.221.1.1.1452.8.2.11.2.3.12.8.2.41.14.14.11.11.1.72.8.2.22.3.1.372.8.2.152.4.1.17

PubMed文献链接

20189629

UniProt数据库

Q5AH87P22309Q06278B7ZS96P49888

KEGG DRUG Database

D00554

BKMS React数据库

1150393269846467891260991997907121147743488910581252511603

BRENDA Ligand数据库

9071284641252567891058126099199793269348891160311503114774

ArrayExpress (Gene Expression Altlas)

E-TABM-12E-TABM-105

HMDB数据库

HMDB0001926

NURSA Database

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

VSDB Database

1,887

SureChEMBL数据库

SCHEMBL4071

ArrayExpress (Repository of Microarray data)

E-TOXM-20

ACToR数据库

406932-93-2

Drug Central Database

GeneOntology数据库

LIPID MAPS Instance

PDB数据库

CompTox数据库

LINCS数据库

Reaxys Registry

数据登录号

化合物性质

理化性质

药理学性质

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

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

法律信息
VETRANAL 商标 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.

描述信息

参考文献

PubChem文献

数据源提供

• 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)

• Counsell, R.E. et al., J. Med. Chem., 1966, 9, 689, (pharmacol)

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

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

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

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

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

• Horvath, G. et al., Adv. Mass Spectrom., 1978, 7B, 1280, (ms)

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

• Ranney, R.E. et al., J. Toxicol. Environ. Health, 1977, 3, 139; 231, (revs, metab)

• Duesterberg, B. et al., Arzneim.-Forsch., 1986, 36, 1187, (pharmacol)

• Newburger, J. et al., Contraception, 1985, 32, 33, (rev, pharmacol)

• Vaalburg, W. et al., J. Labelled Compd. Radiopharm., 1977, 13, 200, (synth)

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

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

商标名

别名

IUPAC标准名

IUPAC传统名

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名称

Ethinyl Estradiol

数据登录号

PubChem CID

Beilstein号

EC号

CAS号

MDL号

PubChem SID

46508618160964315248945852486998911533305

KEGG ID

Medline Plus

DrugBank ID

CHEMBL

美国药典/FDA物质标识码

维基百科标题

ATC码

CHEBI ID

Chemspider ID

Rhea数据库

专利号

EP1640009EP1842521EP1598069WO2005082908WO2006098961US2008051463EP1938798EP1342814US2004072813WO2006060142US2006030555

MetaboLights数据库

MTBLS2145MTBLS4099MTBLS2871MTBLS2457MTBLS1693MTBLS1918

SABIO-RK数据库

139921186014824114901032413994791113888

BRENDA数据库

1.1.1.501.1.1.511.3.1.221.1.1.1452.8.2.11.2.3.12.8.2.41.14.14.11.11.1.72.8.2.22.3.1.372.8.2.152.4.1.17

PubMed文献链接

20189629

UniProt数据库

Q5AH87P22309Q06278B7ZS96P49888

KEGG DRUG Database

D00554

BKMS React数据库

1150393269846467891260991997907121147743488910581252511603

BRENDA Ligand数据库

9071284641252567891058126099199793269348891160311503114774

ArrayExpress (Gene Expression Altlas)

E-TABM-12E-TABM-105

HMDB数据库

HMDB0001926

NURSA Database

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

VSDB Database

1,887

SureChEMBL数据库

SCHEMBL4071

ArrayExpress (Repository of Microarray data)

E-TOXM-20

ACToR数据库

406932-93-2

Drug Central Database

GeneOntology数据库

LIPID MAPS Instance

PDB数据库

CompTox数据库

LINCS数据库

Reaxys Registry

描述信息

DB00977

Drug Groups

approved

Description

Indication

Pharmacology

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]

S1625

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

TRC

E685100

A synthetic steroid with high oral estrogenic potency.

ChEBI

CHEBI:4903

参考文献

PubChem文献

数据源提供