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