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

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