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	17-ethinyl-3,17-oestradiol 17-ethinylestradiol Ethinyloestradiol Ethynyl estradiol 17alpha-Ethinyl estradiol Ethinylestradiolum Ethinylestradiol 17-ethinyl-3,17-estradiol 17α-ethynylestradiol Etinilestradiol Ethinyl estradiol
Brand Names	Pirmella 1/35 Ovral 21 Cyestra-35 Ortho Cyclen Lo-femenal 21 Tablets Larin 24 Fe Evra Tri-lena 21 Sarensis 21 Triphasil 28 Tab Norethindrone acetate and ethinyl estradiol, and ferrous fumarate Fayosim Tri-jordyna 28 Cyonanz Estinyl Tab 0.05mg Min-ovral 21 Tab Aubra Nymyo Cyred Drospirenone and Ethinyl Estradiol Tablets USP 28 Aubra EQ LoJaimiess Rhuzdah Zenchent 0.4/35 Microgestin Fe Yasmin Kimidess MICROGESTIN Fe 1/20 Tri-lena Lo 28 Yasmin Plus Pirmella 7/7/7 Diane-35 Tri-cyclen Tablets - 28-day Ortho 10/11 Tablets (28 Day) Simliya Tri-jordyna 21 Lo Loestrin Fe Yasmin 28 Ortho-novum 10/11 Kelnor 1/50 Lo/Ovral-28 Laylaa 21 Levlite Norgestimate and Ethinyl Estradiol NuvaRing Cyred EQ Jinteli Levonorgestrel and Ethinyl Estradoil Centrisa 28 Hailey 1.5/30 Tri-Sprintec Chateal EQ Ovcon 35 Synphasic-28 Tablets Aviane 28 Norgestimate and ethinyl estradiol Yasmin 21 Microgestin Fe 1/20 Apri 28 Centrisa 21 Necon 777 777 Zarah 28 Cryselle Yaz Cléo -35 Finzala Vienva Tm Portia 21 Seasonique Emoquette Gemmily Iclevia Brevicon 0.5/35 Tablets (28-day Pack) Tri-VyLibra Demulen 50 (21 Day Pack) Kaitlib Fe Marfem 28 Melodetta 24 Fe Norethindrone Acetate and Ethinyl Estradiol and Ferrous Fumarate Taysofy Zamine 21 EnilloRing Microgestin 24 Fe Isibloom Lo Minastrin Fe Demulen 50 (28 Day Pack) LoSeasonique Nortrel 7/7/7 (28 Day Regimen) Necon (28 Day Regimen) Tri-Estarylla TriNessa Lo Loestrin 21 1/20 Drospirenone/Ethinyl Estradiol/Levomefolate Calcium and Levomefolate Calcium Falessa Nexesta Fe Aurovela Fe 1/20 Ovima 21 Necon 777 Taro-cyproterone/ethinyl Estradiol Brevicon 1/35 Tablets (28-day Pack) Larin Fe 1/20 Tri-Legest Fe 28 Day Tri-Previfem Lessina Lo/Ovral LOESTRIN Fe 1/20 Aranelle Cyclafem 7/7/7 Necon 1/35 Ogestrel Drospirenone/ethinyl estradiol/levomefolate calcium and levomefolate calcium Desogestrel and Ethinyl Estradiol Altavera Lo/ovral-28 Etonogestrel and Ethinyl Estradiol Vaginal Norethindrone and ethinyl estradiol Mili Nikki Previfem Chateal Desogestrel and Ethinyl Estradiol and Ethinyl Estradiol Tri-cyclen Lo (21 Day) LOESTRIN 1/20 21 Day Balcoltra Synphasic 28 Tablets Brevicon Blisovi 24 Fe Bekyree Aurovela 1.5/30 Seasonale Levonest Triquilar 28 Desogen Ovral 28tab Generess Merzee Ovcon 50 EluRyng FEMCON Fe Levonorgestrel and Ethinyl Estradiol and Ethinyl Estradiol Zafemy Lomedia 24 Fe Drospirenone and Ethinyl Estradiol Tablets USP 21 Tri-cira 28 Vienva Preven Emergency Contraceptive HAILEY Fe 1/20 Femynor Etonogestrel and Ethinyl Estradiol Vaginal Ring Hailey Fe 1.5/30 Loryna Teva-cyproterone / Ethinyl Estradiol Ocella Ortho 1/35 Tablets (21 Day) Ayuna Orsythia Nordette Blisovi Fe 1/20 Joyeaux Loestrin 21 1.5/30 Marlissa Microgestin Drospirenone and Ethinyl Estradiol Tablets Aviane 28 Day Lo Simpesse Mono-Linyah Zovia 1/35 Indayo Mylan-cyproterone / Ethinylestradiol Ovral 28 Tablets Quasense Evra -(6/0.75) Apri Low-Ogestrel Alesse 21 Junel Fe 24 Loestrin Fe 28 Day Synphasic 21 Tablets Zarah Azurette Myvlar Trivora Freya 28 Levonorgestrel and Ethinyl Estradiol Introvale Amethia Preven Tablets Ortho 7/7/7 Tablets (21 Day) Tri-previfem (21 Day) Drospirenone and Ethinyl Estradiol Tablets 21 Tarina 24 Fe Microgestin 1.5/30 Tri-Lo- Estarylla Vyfemla Linessa 21 Tilia Fe Xulane Jasmiel Ovral 21 Tab Centrisa Lo 21 Triquilar 21 Tri-lena Lo 21 Ortho Novum 135 Alyacen 1/35 Portia 28 Ortho 7/7/7 Tablets (28 Day) Aviane Ortho 0.5/35 Tablets (21 Day) Mirvala 21 Lo-Zumandimine Zeosa Tri-cira Lo 21 Min-ovral 28 Tab Afirmelle Zovia 1/35E-28 Ortho Tri Cyclen Quartette Jaimiess Mono-linyah Quaterna Aurovela 1/20 Gildess 1.5/30 Cyclen Tablets (21 Day) Microgestin Fe 1.5/30 Briellyn Norelgestromin and Ethinyl Estradiol Sarensis 28 Turqoz Zarah 21 Caziant Tri-Linyah Mercilon Tri-cyclen Tablets - 21-day Annovera Tri-Lo-Sprintec Reclipsen 21 Tarina Fe 1/20 EQ Ashlyna Gianvi Apri 21 Sprintec Demulen 30 (28 Day Pack) Marvelon 21 Lutera 28 Esme 28 Femlyv Zenchent Ortho 0.5/35 Tablets (28 Day) Dasetta 7/7/7 LOESTRIN Fe 1.5/30 Freya 21 Min-ovral 28 Reclipsen Viorele Delyla Hailey 24 Fe Necon Apri 28 Day Reclipsen 28 Day Tri Femynor Lybrel camrese Lo Demulen 30 (21 Day Pack) Mibelas 24 Fe Pimtrea Leena Alyacen 7/7/7 Elinest LOESTRIN 1.5/30 21 Day Necon 1/35 (28 Day Regimen) Tri-VyLibra Lo VyLibra Estinyl Tablets 0.02 Mg. Junel FE Ortho Tri-Cyclen Select 1/35 (21-day) Kurvelo Mircette Tri-cira Lo 28 Tri-Lo-Mili Linessa 28 Enpresse Tri-LO-marzia Brevicon 1/35 Tablets (21-day Pack) Kalliga Brevicon 1/35 21 Tab Norethindrone and Ethinyl Estradiol and Ferrous Fumarate Ortho 1/35 Tablets (28 Day) Lillow LOESTRIN Fe 1.5/30 28 Day Lutera Falmina Alysena 28 Ortho-cept Tablets (28 Day) Volnea Tyblume Safyral Ethynodiol Diacetate and Ethinyl Estradiol Junel Fe 1/20 Ortho Cept Wymzya Fe Audrina 28 Cyclessa Ortho-Novum 777 Larissia Nylia 7/7/7 Tri-Nymyo Aviane 21 Gildess 24 Fe Kelnor 1/35 Rivelsa Kariva Ortho 10/11 Tablets (21 Day) Ortho Evra Brevicon 0.5/35 21 Tab Alesse 28 Qismette 28 Syeda Vienva TM Portia Larin 1.5/30 Enskyce Simpesse Amethia Lo Marfem 21 Minivlar 30 Tri-Norinyl Nortrel 21 Day Caziant Triphasic Regimen LOESTRIN Fe 1/20 28 Day Drospirenone and ethinyl estradiol Myzilra Estarylla Velivet Triphasic Regimen Triphasil-21 Daysee Tydemy Norethindrone and ethinyl estradiol and ferrous fumarate WYMZYA Fe Wera Aurovela 24 Fe Nortrel 28 Day Previfem (21day) Junel 21 Day Loestrin 24 Fe Fyavolv Levora Junel 1.5/30 Haloette Modicon Loestrin 21 Day Junel Fe 1.5/30 Zenchent FE Tri-cira 21 Etonogestrel/Ethinyl Estradiol Setlakin Norgestrel/Ethinyl Estradiol Minastrin 24 Fe Cesia Minzoya Reclipsen 28 Twirla Gildess 1/20 Sronyx Triphasil 28 Jolessa ESTROSTEP Fe Larin Fe 1.5/30 Levonorgetsrel and Ethinyl Estradiol Mirvala 28 Loestrin 1.5/30 Balziva Norinyl Tri-lena 28 Taytulla Tri-cyclen Lo (28 Day) Jevantique Layolis Fe Ovima 28 Brevicon 1/35 28 Tab Alysena 21 Drospirenone, Ethinyl Estradiol and Levomefolate Calcium and Levomefolate Calcium Norethindrone and Ethinyl Estradiol, and Ferrous Fumarate Tri-Mili Brevicon 0.5/35 Tablets (21-day Pack) Blisovi Fe 1.5/30 Qismette 21 Camrese Zumandimine Junel Fe 28 Day TARINA Fe 1/20 Beyaz Necon 0.5/35 Drospirenone and Ethinyl Estradiol Tablets USP Nuvaring MICROGESTIN Fe 1.5/30 Lo-ovral-28 AUROVELA Fe GENERESS Fe MonoNessa Brevicon 0.5/35 28 Tab Gildess Fe 1/20 Juleber Drospirenone and Ethinyl estradiol Femhrt Lolo Etonogestrel and Ethinyl Estradiol Tri-previfem (28 Day) Desogestrel/Ethinyl Estradiol and Ethinyl Estradiol Estinyl Tab 0.5mg Necon 10/11 Nortrel (21 Day Regimen) Mya Drospirenone and Ethinyl Estradiol Tablets 28 ORTHO TRI CYCLEN Lo Select 1/35 (28-day) Triphasil 21 Rajani Ortho-cept Tablets (21 Day) Min-ovral 21 Audrina 21 Zamine 28 Gildess Fe 1.5/30 TriNessa Dolishale Dasetta 1/35 Norethindrone Acetate and Ethinyl Estradiol Norethindrone Acetate and Ethinyl Estradiol, and Ferrous Fumarate Centrisa Lo 28 Philith Esme 21 Gildagia Larin 1/20 Minestrin 1/20 Yaz Plus Oshih Amethyst Lutera 21 Cyclafem 1/35 Drospirenone and Ethinyl Estradiol Vestura Norelgestromin and Ethinly Estradiol Zovia 1/50E-28 Charlotte 24Fe Solia Microgestin 1/20 Triphasil 21 Tab Nylia 1/35 Previfem (28day) Ortho Novum 1/35 Cyclen Tablets (28 Day) Marvelon 28 Jevantique Lo Laylaa 28
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