3WF

Ethinyl estradiol

Created:	2014-11-26
Last modified:	2015-09-09

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3 entries where 3WF is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	46
Chiral Atom Count	5
Bond Count	49
Aromatic Bond Count	6

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Chemical Component Summary
Name	Ethinyl estradiol
Systematic Name (OpenEye OEToolkits)	(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Formula	C₂₀ H₂₄ O₂
Molecular Weight	296.403
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	Oc1cc4c(cc1)C3CCC2(C(CCC2(C#C)O)C3CC4)C
SMILES	CACTVS	3.385	C[C]12CC[CH]3[CH](CCc4cc(O)ccc34)[CH]1CC[C]2(O)C#C
SMILES	OpenEye OEToolkits	1.9.2	CC12CCC3c4ccc(cc4CCC3C1CCC2(C#C)O)O
Canonical SMILES	CACTVS	3.385	C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1CC[C@@]2(O)C#C
Canonical SMILES	OpenEye OEToolkits	1.9.2	C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1CC[C@]2(C#C)O)O
InChI	InChI	1.03	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	InChI	1.03	BFPYWIDHMRZLRN-SLHNCBLASA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB00977 ?
Name	Ethinylestradiol
Groups	approved
Description	Ethinylestradiol was first synthesized in 1938 by Hans Herloff Inhoffen and Walter Hohlweg at Schering.[A191107] It was developed in an effort to create an estrogen with greater oral bioavailability.[A191107] These properties were achieved by the substitution of an ethinyl group at carbon 17 of [estradiol].[A191107] Ethinylestradiol soon replaced [mestranol] in contraceptive pills.[A191107] Ethinylestradiol was granted FDA approval on 25 June 1943.[L11884]
Synonyms	Ethynyl estradiol 17alpha-Ethinyl estradiol Ethinyl estradiol Ethinylestradiol 17-ethinyl-3,17-oestradiol Ethinylestradiolum 17-ethinyl-3,17-estradiol Etinilestradiol 17-ethinylestradiol Ethinyloestradiol 17α-ethynylestradiol
Brand Names	Zenchent Select 1/35 (28-day) TriNessa Norethindrone acetate and ethinyl estradiol, and ferrous fumarate Portia 21 Drospirenone and Ethinyl Estradiol Tablets 28 Drospirenone and ethinyl estradiol Evra Marfem 28 Apri 21 Etonogestrel and Ethinyl Estradiol Vaginal Norgestimate and Ethinyl Estradiol Min-ovral 21 Myzilra Juleber GENERESS Fe Mili Blisovi Fe 1.5/30 Kelnor 1/35 Mirvala 21 Alesse 21 camrese Lo Centrisa Lo 28 Dolishale Xulane Norethindrone Acetate and Ethinyl Estradiol and Ferrous Fumarate Aviane Mono-Linyah Aviane 28 WYMZYA Fe Balziva Yasmin Plus Drospirenone and Ethinyl Estradiol Tablets USP 28 Femynor Loestrin 21 Day Tri-Nymyo Loestrin 1.5/30 Norgestrel/Ethinyl Estradiol Tri-VyLibra Zovia 1/35E-28 Blisovi 24 Fe Cyclafem 1/35 Mibelas 24 Fe Marvelon 21 Fyavolv Tri-Lo- Estarylla Norethindrone Acetate and Ethinyl Estradiol, and Ferrous Fumarate Caziant Triphasic Regimen Estinyl Tab 0.5mg Apri 28 Day Centrisa 21 Ortho Novum 1/35 Minivlar 30 Nortrel 21 Day Previfem Lo/Ovral Tilia Fe Cryselle Camrese Tri-LO-marzia Drospirenone/ethinyl estradiol/levomefolate calcium and levomefolate calcium Blisovi Fe 1/20 Balcoltra Levonorgestrel and Ethinyl Estradiol and Ethinyl Estradiol Zarah 21 Nymyo Tri-cira 28 Tri-cira 21 Chateal Tri-Legest Fe 28 Day Centrisa Lo 21 LoJaimiess Melodetta 24 Fe Viorele Gildess Fe 1.5/30 Microgestin 24 Fe Tri-lena Lo 21 Sarensis 21 Select 1/35 (21-day) Delyla Lo Loestrin Fe Brevicon 0.5/35 21 Tab Vestura Portia 28 Estinyl Tab 0.05mg Reclipsen Dasetta 1/35 Rhuzdah Ovima 28 Teva-cyproterone / Ethinyl Estradiol Seasonale Tri-Lo-Sprintec Mircette Syeda Esme 21 LOESTRIN 1/20 21 Day Estinyl Tablets 0.02 Mg. Necon 1/35 (28 Day Regimen) Etonogestrel and Ethinyl Estradiol Vaginal Ring Simpesse Tri-cira Lo 28 Femhrt Mirvala 28 Ethynodiol Diacetate and Ethinyl Estradiol Indayo Iclevia Tri-cyclen Lo (21 Day) Lo Simpesse Amethyst Cyred EQ Tri-previfem (21 Day) Kurvelo Marvelon 28 Marlissa Jevantique Nortrel 28 Day Gildagia Layolis Fe Ortho Evra Ocella Leena Lillow Brevicon 0.5/35 28 Tab Ortho-Novum 777 Levonorgetsrel and Ethinyl Estradiol Introvale Sarensis 28 Dasetta 7/7/7 Tri-Estarylla Junel Fe 1/20 Aviane 21 Ortho 1/35 Tablets (21 Day) Zafemy Zamine 28 Drospirenone/Ethinyl Estradiol/Levomefolate Calcium and Levomefolate Calcium Nylia 1/35 Lomedia 24 Fe Minestrin 1/20 Tri-Lo-Mili Junel FE Necon 777 777 Linessa 21 Norethindrone and ethinyl estradiol Zumandimine Mylan-cyproterone / Ethinylestradiol TARINA Fe 1/20 Aurovela 1/20 Nortrel 7/7/7 (28 Day Regimen) Quartette Amethia Levonest Minastrin 24 Fe Caziant Lo-ovral-28 Reclipsen 21 Tri-Mili Vyfemla Yasmin 28 Aurovela 24 Fe Larin 1/20 Lolo Brevicon 1/35 28 Tab Norgestimate and ethinyl estradiol Reclipsen 28 Ovcon 35 MICROGESTIN Fe 1.5/30 Microgestin 1.5/30 Quasense Orsythia Drospirenone and Ethinyl Estradiol Jaimiess Etonogestrel and Ethinyl Estradiol Demulen 50 (28 Day Pack) Loestrin 24 Fe Audrina 28 Vienva Zenchent FE Finzala LOESTRIN Fe 1/20 28 Day Setlakin Synphasic 21 Tablets Zamine 21 Kariva Brevicon Vienva TM Hailey Fe 1.5/30 Lessina Hailey 24 Fe Ortho 0.5/35 Tablets (21 Day) Tri-previfem (28 Day) Safyral Larin Fe 1.5/30 Demulen 30 (28 Day Pack) Norinyl Aurovela 1.5/30 Microgestin 1/20 Ayuna Necon 10/11 Trivora Junel 21 Day MonoNessa Taro-cyproterone/ethinyl Estradiol Ortho-cept Tablets (21 Day) Oshih Freya 21 Tydemy Tyblume Tri-jordyna 21 Esme 28 Enskyce Tri Femynor Generess Taytulla Ortho Tri Cyclen Loestrin Fe 28 Day Pimtrea VyLibra Volnea Zeosa Drospirenone and Ethinyl Estradiol Tablets 21 Afirmelle HAILEY Fe 1/20 Evra -(6/0.75) Alysena 28 Minzoya Cléo -35 Norelgestromin and Ethinyl Estradiol Seasonique Fayosim Preven Emergency Contraceptive Ortho 1/35 Tablets (28 Day) Yaz Modicon Alyacen 1/35 Aurovela Fe 1/20 Preven Tablets Cyclen Tablets (21 Day) Ovral 28tab Falmina Tri-jordyna 28 Charlotte 24Fe Turqoz Ovral 21 Tab Cesia Triphasil 28 Tab LOESTRIN 1.5/30 21 Day Rajani NuvaRing Necon 0.5/35 Alyacen 7/7/7 Microgestin Microgestin Fe 1/20 Aranelle Desogen Philith Tri-cyclen Lo (28 Day) ESTROSTEP Fe Wymzya Fe Drospirenone and Ethinyl estradiol Norelgestromin and Ethinly Estradiol Ovral 28 Tablets Elinest Larissia Nortrel (21 Day Regimen) Low-Ogestrel Junel Fe 24 Gildess 1.5/30 Chateal EQ Gianvi Lutera 28 Demulen 50 (21 Day Pack) Taysofy Ortho 0.5/35 Tablets (28 Day) Nylia 7/7/7 Zarah Hailey 1.5/30 Annovera Beyaz Levonorgestrel and Ethinyl Estradiol Desogestrel and Ethinyl Estradiol Drospirenone and Ethinyl Estradiol Tablets Cyred Merzee Nuvaring Tri-cyclen Tablets - 21-day Ortho 7/7/7 Tablets (28 Day) Drospirenone and Ethinyl Estradiol Tablets USP 21 Quaterna Linessa 28 Levlite Zovia 1/35 Amethia Lo Etonogestrel/Ethinyl Estradiol Levora Triphasil 28 Kalliga Ortho Cept ORTHO TRI CYCLEN Lo Desogestrel and Ethinyl Estradiol and Ethinyl Estradiol Tri-VyLibra Lo Brevicon 0.5/35 Tablets (21-day Pack) Jinteli Larin 24 Fe Ogestrel Lo-Zumandimine Brevicon 0.5/35 Tablets (28-day Pack) Necon 777 Nordette Cyclafem 7/7/7 Laylaa 21 Freya 28 Ovima 21 Briellyn Gildess 1/20 Haloette Diane-35 Tri-cyclen Tablets - 28-day Reclipsen 28 Day Velivet Triphasic Regimen Tri-cira Lo 21 Emoquette Drospirenone and Ethinyl Estradiol Tablets USP Lutera 21 EluRyng MICROGESTIN Fe 1/20 Sprintec Vienva Tm Zarah 28 Qismette 28 Pirmella 1/35 Loestrin 21 1.5/30 Sronyx Nexesta Fe Aubra EQ Alysena 21 Junel 1.5/30 Norethindrone and ethinyl estradiol and ferrous fumarate Ortho 7/7/7 Tablets (21 Day) Yasmin Gildess 24 Fe Cyonanz Femlyv Junel Fe 28 Day Lo/ovral-28 Ortho-cept Tablets (28 Day) Tarina 24 Fe Necon (28 Day Regimen) Azurette Mercilon Microgestin Fe 1.5/30 Estarylla Centrisa 28 Enpresse LOESTRIN Fe 1/20 Lutera Pirmella 7/7/7 Demulen 30 (21 Day Pack) Synphasic 28 Tablets Bekyree Norethindrone and Ethinyl Estradiol and Ferrous Fumarate Jasmiel Rivelsa Audrina 21 FEMCON Fe Tri-Sprintec Yaz Plus Lo/Ovral-28 Ortho-novum 10/11 Previfem (21day) Cyestra-35 Myvlar Aubra Triquilar 28 Triphasil 21 Ortho Cyclen Desogestrel/Ethinyl Estradiol and Ethinyl Estradiol Brevicon 1/35 21 Tab Qismette 21 AUROVELA Fe Laylaa 28 Alesse 28 Apri 28 Min-ovral 28 Tab Jevantique Lo Lybrel Marfem 21 Drospirenone, Ethinyl Estradiol and Levomefolate Calcium and Levomefolate Calcium LoSeasonique Mono-linyah Tri-Norinyl Altavera Norethindrone and Ethinyl Estradiol, and Ferrous Fumarate Isibloom Mya Ovral 21 Daysee Kaitlib Fe LOESTRIN Fe 1.5/30 Necon Tri-lena 21 Ortho Novum 135 Ortho Tri-Cyclen Triphasil-21 Levonorgestrel and Ethinyl Estradoil Cyclessa Larin Fe 1/20 Gemmily Nikki EnilloRing Tri-lena Lo 28 Zovia 1/50E-28 Ashlyna Triphasil 21 Tab Ortho 10/11 Tablets (28 Day) Falessa Brevicon 1/35 Tablets (28-day Pack) Min-ovral 28 Loestrin 21 1/20 Tri-lena 28 Gildess Fe 1/20 Larin 1.5/30 Min-ovral 21 Tab Cyclen Tablets (28 Day) Necon 1/35 Twirla Solia Tri-Previfem Zenchent 0.4/35 Junel Fe 1.5/30 Triquilar 21 Tri-Linyah Lo Minastrin Fe Portia LOESTRIN Fe 1.5/30 28 Day Loryna Brevicon 1/35 Tablets (21-day Pack) Lo-femenal 21 Tablets Joyeaux Microgestin Fe Yasmin 21 Apri TriNessa Lo Kelnor 1/50 Ovcon 50 Kimidess Previfem (28day) Norethindrone Acetate and Ethinyl Estradiol Aviane 28 Day Tarina Fe 1/20 EQ Jolessa Ortho 10/11 Tablets (21 Day) Simliya Synphasic-28 Tablets Wera
Indication	Ethinylestradiol is combined with other drugs for use as a contraceptive, premenstrual dysphoric disorder, moderate acne, moderate to severe vasomotor symptoms of menopause, prevention of postmenopausal osteoporosis.[L11944,L11965,L11947,L11950,L11845,L9806,L11953,L10304,L11956,L11959,L11962]
Categories	Adrenal Cortex Hormones Antineoplastic and Immunomodulating Agents BSEP/ABCB11 inducers BSEP/ABCB11 Inhibitors COMT Substrates Contraceptive Agents, Female Contraceptive Agents, Hormonal Contraceptives, Oral Contraceptives, Oral, Hormonal Contraceptives, Postcoital Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 inhibitors (strength unknown) Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Endocrine Therapy Estradiol Congeners Estrogen Contraceptives Estrogenic Steroids, Alkylated Estrogens Fused-Ring Compounds Genito Urinary System and Sex Hormones Gonadal Hormones Gonadal Steroid Hormones Hormonal Contraceptives for Systemic Use Hormones Hormones and Related Agents Hormones, Hormone Substitutes, and Hormone Antagonists Hyperglycemia-Associated Agents Natural and Semisynthetic Estrogens, Plain Norpregnanes Norpregnatrienes Norsteroids P-glycoprotein substrates Progestogens and Estrogens, Sequential Preparations Reproductive Control Agents Sex Hormones and Modulators of the Genital System Steroids Thyroxine-binding globulin inducers UGT1A1 Inducers UGT1A1 Substrates UGT1A4 substrates UGT1A9 Substrates UGT2B7 substrates
ATC-Code	G03AA15 G03AA11 L02AA03 G03AA12 G03AA16 G03AB02 G03CA01 G03AA03 G03AA10 G03AB04 G03AB01 G03AB07 G03AA13 G03AA06 G03AA08 G03AA02 G03AA04 G03AA09 G03AB09 G03AA07 G03AB03 G03AA05 G03AB05 G03AB06 G03AA01
CAS number	57-63-6

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Estrogen receptor	MTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...	unknown	agonist
Nuclear receptor subfamily 1 group I member 2	MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...	unknown	agonist
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate,inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
UDP-glucuronosyltransferase 1A4	MARGLQVPLPRLATGLLLLLSVQPWAESGKVLVVPTDGSPWLSMREALRE...	unknown	substrate
UDP-glucuronosyltransferase 1A3	MATGLQVPLPWLATGLLLLLSVQPWAESGKVLVVPIDGSHWLSMREVLRE...	unknown
UDP-glucuronosyltransferase 1A1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	substrate,inducer
UDP-glucuronosyltransferase 1A9	MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 2B7	MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...	unknown	substrate
Sulfotransferase 1A3	MELIQDTSRPPLEYVKGVPLIKYFAEALGPLQSFQARPDDLLINTYPKSG...	unknown	substrate
Sulfotransferase 1E1	MNSELDYYEKFEEVHGILMYKDFVKYWDNVEAFQARPDDLVIATYPKSGT...	unknown	substrate
Catechol O-methyltransferase	MPEAPPLLLAAVLLGLVLLVVLLLLLRHWGWGLCLIGWNEFILQPIHNLL...	unknown	substrate
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	inhibitor
Albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Sex hormone-binding globulin	MESRGPLATSRLLLLLLLLLLRHTRQGWALRPVLPTQSAHDPPAVHLSNG...	unknown	binder
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	inhibitor
Hepatic sodium/bile acid cotransporter	MEAHNASAPFNFTLPPNFGKRPTDLALSVILVFMLFFIMLSLGCTMEFSK...	unknown	inhibitor
ATP-binding cassette sub-family C member 2	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	inhibitor,inducer
ATP-dependent translocase ABCB1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource Name	Reference
Pharos	CHEMBL691
PubChem	5991
ChEMBL	CHEMBL691
ChEBI	CHEBI:4903
CCDC/CSD	MIFPOI, PEPVOY, VOBNEG, NOTBOQ, MIFQID, FISWIN, FISWIN01, VOBMIJ, NOTCAD, VOBMOP, MIFRAW, VOBNIK, MIFPAU, VOBNAC, NOTDOS, VOBMIJ01, VOBNEG01