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Showing drug card for Ethinyl Estradiol (DB00977)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:33
Primary Accession Number DB00977
Secondary Accession Number
  • APRD00691
Name Ethinyl Estradiol
Drug Type
  • Approved
  • Small Molecule
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]
Synonyms
  1. 17 alpha-Ethinylestradiol
  2. 17 alpha-Ethynylestradiol
  3. 17 alpha-Ethynyloestradiol
  4. Aethinyloestradiolum
  5. Aethinyoestradiol [German]
  6. EE
  7. EO
  8. Ethinyl-Oestranol
  9. Ethinylestradiolum [INN-Latin]
  10. Ethinylestriol
  11. Ethinyloestradiol
  12. Ethynylestradiol
  13. Ethynyloestradiol
  14. Etinilestradiol [INN-Spanish]
Brand Names
  1. Amenoron
  2. Amenorone
  3. Anovlar
  4. Cyclosa
  5. Dicromil
  6. Diognat-E
  7. Diogyn E
  8. Diogyn-E
  9. Diprol
  10. Dyloform
  11. Ertonyl
  12. Esteed
  13. Estigyn
  14. Eston-E
  15. Estopherol
  16. Estoral
  17. Estorals
  18. Ethidol
  19. Ethinoral
  20. Ethy 11
  21. Eticyclin
  22. Eticyclol
  23. Eticylol
  24. Etinestrol
  25. Etinestryl
  26. Etinoestryl
  27. Etistradiol
  28. Etivex
  29. Follicoral
  30. Ginestrene
  31. Gynolett
  32. Halodrin
  33. Inestra
  34. Kolpolyn
  35. Linoral
  36. Marvelon
  37. Menolyn
  38. Mercilon
  39. Microfollin
  40. Neo-Estrone
  41. Nogest-S
  42. Novestrol
  43. Oradiol
  44. Orestralyn
  45. Orestrayln
  46. Ortho-Cyclen
  47. Oviol
  48. Primogyn
  49. Primogyn C
  50. Primogyn M
  51. Progynon C
  52. Progynon M
  53. Prosexol
  54. Spanestrin
  55. Varnoline
  56. Ylestrol
Brand Mixtures
  1. Alesse 21 Tablets (Ethinyl Estradiol + Levonorgestrel)
  2. Alesse 28 Tablets (Ethinyl Estradiol + Levonorgestrel)
  3. Brevicon (Ethinyl Estradiol + Norethindrone)
  4. Cyclen (Ethinyl Estradiol + Norgestimate)
  5. Demulen 30 (Ethinyl Estradiol + Ethynodiol Diacetate)
  6. Demulen 50 (Ethinyl Estradiol + Ethynodiol Diacetate)
  7. Diane-35 (Cyproterone Acetate + Ethinyl Estradiol)
  8. Evra (Ethinyl Estradiol + Norelgestromin)
  9. Femhrt 1/5 (Ethinyl Estradiol + Norethindrone Acetate)
  10. Geri Bons Tab (Calcium (Calcium Phosphate (Dibasic)) + Copper + Dl-Methionine + Ethinyl Estradiol + Fatty Acids + Folic Acid + Iodine + Iron Peptonized + Magnesium + Manganese + Methyltestosterone + Nicotinamide + Phosphorus (Calcium Phosphate (Dibasic)) + Pyridoxine Hydrochloride + Thiamine Hydrochloride + Thyroid + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D + Vitamin E)
  11. Geri Tabs (Calcium (Calcium Phosphate (Dibasic)) + Copper Sulfate + Dl-Methionine + Ethinyl Estradiol + Folic Acid + Iodine + Iron Peptonized + Magnesium Oxide + Manganese Sulfate + Methyltestosterone + Nicotinamide + Phosphorus (Calcium Phosphate (Dibasic)) + Pyridoxine Hydrochloride + Thiamine Hydrochloride + Thyroid + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D + Vitamin E)
  12. Lo-Femenal 21 Tablets (Ethinyl Estradiol + Norgestrel)
  13. Loestrin 1.5/30 21day Pak (Ethinyl Estradiol + Norethindrone Acetate)
  14. Loestrin 1.5/30 28day Pack (Ethinyl Estradiol + Norethindrone Acetate)
  15. Marvelon 21 Tab (Desogestrel + Ethinyl Estradiol)
  16. Marvelon 28 Tab (Desogestrel + Ethinyl Estradiol)
  17. Min-Ovral 21 (Ethinyl Estradiol + Levonorgestrel)
  18. Min-Ovral 21 Tab (Ethinyl Estradiol + Levonorgestrel)
  19. Min-Ovral 28 (Ethinyl Estradiol + Levonorgestrel)
  20. Min-Ovral 28 Tab (Ethinyl Estradiol + Levonorgestrel)
  21. Minestrin 1/20 21 (Ethinyl Estradiol + Norethindrone Acetate)
  22. Minestrin 1/20 28 (Ethinyl Estradiol + Norethindrone Acetate)
  23. Neo Mens Tab (Ethinyl Estradiol + Ethisterone)
  24. Nuvaring (Ethinyl Estradiol + Etonogestrel)
  25. Ortho Tablets (0.5/35, 1/35, 10/11, 7/7/7) (Ethinyl Estradiol + Norethindrone)
  26. Ortho-Cept Tablets (Desogestrel + Ethinyl Estradiol)
  27. Ovral 21 Tab (Ethinyl Estradiol + Norgestrel (Norgestrel))
  28. Ovral 21 Tablets (Ethinyl Estradiol + Norgestrel (Norgestrel))
  29. Ovral 28 Tablets (Ethinyl Estradiol + Norgestrel (Norgestrel))
  30. Ovral 28tab (Ethinyl Estradiol + Norgestrel)
  31. Preven Tablets (Ethinyl Estradiol + Levonorgestrel)
  32. Select 1/35 (Ethinyl Estradiol + Norethindrone)
  33. Synphasic 21 Tablets (Ethinyl Estradiol + Norethindrone)
  34. Synphasic 28 Tablets (Ethinyl Estradiol + Norethindrone)
  35. Synphasic-28 Tablets (Ethinyl Estradiol + Norethindrone)
  36. Tri-Cyclen Lo (Ethinyl Estradiol + Norgestimate)
  37. Tri-Cyclen Tablets - 21-Day (Ethinyl Estradiol + Norgestimate)
  38. Tri-Cyclen Tablets - 28-Day (Ethinyl Estradiol + Norgestimate)
  39. Triphasil 21 (Ethinyl Estradiol + Levonorgestrel)
  40. Triphasil 21 Tab (Ethinyl Estradiol + Levonorgestrel)
  41. Triphasil 28 (Ethinyl Estradiol + Levonorgestrel)
  42. Triphasil 28 Tab (Ethinyl Estradiol + Levonorgestrel)
  43. Triquilar 21 Tab (Ethinyl Estradiol + Levonorgestrel)
  44. Triquilar 28 Tab (Ethinyl Estradiol + Levonorgestrel)
  45. Yasmin 21 (Drospirenone + Ethinyl Estradiol)
  46. Yasmin 28 (Drospirenone + Ethinyl Estradiol)
Chemical IUPAC Name (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
Chemical Formula C20H24O2
Chemical Structure Structure
CAS Registry Number 57-63-6
InChI Identifier InChI=1/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
InChI Key BFPYWIDHMRZLRN-SLHNCBLABF
KEGG Drug D00554 Link Image
KEGG Compound C07534 Link Image
PubChem Compound 5991 Link Image
PubChem Substance 148835 Link Image
ChEBI ID 4903 Link Image
PharmGKB ID PA449527 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00028231 Link Image
RxList Link http://www.rxlist.com/cgi/generic/estinyl.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Ethinylestradiol Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Inhofen et al., Ber. 71, 1024(1938)
Average Molecular Weight 296.4034
Monoisotopic Molecular Weight 296.1776
State Solid
Melting Point 183 oC
Experimental Water Solubility 11.3 mg/L Source: PhysProp
Predicted Water Solubility 6.77e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 4.3 Source: PhysProp
Predicted LogP 3.63 Calculated using ALOGPS
Experimental LogS -4.3 [ADME Research, USCD]
Predicted LogS -4.64 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1CC[C@@]2(O)C#C
Canonical SMILES CC12CCC3C(CCC4=C3C=CC(O)=C4)C1CCC2(O)C#C
Drug Category
  • Estrogens
ATC Codes
AHFS Codes Not Available
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.
Mechanism of Action Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
Absorption Rapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).
Toxicity Oral, mouse LD50: 1737 mg/kg. Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Protein Binding 97%
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.
Half Life 36 +/- 13 hours
Dosage Forms
Form Route
Cream Intravaginal
Insert, extended release Transdermal
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol Increased thrombotic risk due to estrogen
Aminophylline The contraceptive increases the effect and toxicity of theophylline
Amobarbital This product may cause a slight decrease of contraceptive effect
Amoxicillin This anti-infectious agent could decrease the effect of the oral contraceptive
Ampicillin This anti-infectious agent could decrease the effect of the oral contraceptive
Amprenavir Ritonavir could decrease the contraceptive efficacy
Anisindione Increased thrombotic risk due to estrogen
Aprepitant Aprepitant could decrease the effect of the oral contraceptive
Aprobarbital This product may cause a slight decrease of contraceptive effect
Azlocillin This anti-infectious agent could decrease the effect of the oral contraceptive
Aztreonam This anti-infectious agent could decrease the effect of the oral contraceptive
Bacampicillin This anti-infectious agent could decrease the effect of the oral contraceptive
Bosentan Bosentan decreases the effect of contraceptive
Butabarbital This product may cause a slight decrease of contraceptive effect
Butalbital This product may cause a slight decrease of contraceptive effect
Butethal This product may cause a slight decrease of contraceptive effect
Carbamazepine This product may cause a slight decrease of contraceptive effect
Carbenicillin This anti-infectious agent could decrease the effect of the oral contraceptive
Clavulanate This anti-infectious agent could decrease the effect of the oral contraceptive
Cloxacillin This anti-infectious agent could decrease the effect of the oral contraceptive
Cyclacillin This anti-infectious agent could decrease the effect of the oral contraceptive
Cyclosporine The contraceptive increases the effect and toxicity of cyclosporine
Demeclocycline This anti-infectious agent could decrease the effect of the oral contraceptive
Dicloxacillin This anti-infectious agent could decrease the effect of the oral contraceptive
Dicumarol Increased thrombotic risk due to estrogen
Doxycycline This anti-infectious agent could decrease the effect of the oral contraceptive
Dyphylline The contraceptive increases the effect and toxicity of theophylline
Ethotoin This product may cause a slight decrease of contraceptive effect
Etoricoxib Etoricoxib increases the levels of ethinyl estradiol
Flucloxacillin This anti-infectious agent could decrease the effect of the oral contraceptive
Fosphenytoin This product may cause a slight decrease of contraceptive effect
Griseofulvin This product may cause a slight decrease of contraceptive effect
Heptabarbital This product may cause a slight decrease of contraceptive effect
Hetacillin This anti-infectious agent could decrease the effect of the oral contraceptive
Hexobarbital This product may cause a slight decrease of contraceptive effect
Itraconazole This anti-infectious agent could decrease the effect of the oral contraceptive
Ketoconazole This anti-infectious agent could decrease the effect of the oral contraceptive
Lamotrigine The oral contraceptive decreases the effect of lamotrigine
Mephenytoin This product may cause a slight decrease of contraceptive effect
Methacycline This anti-infectious agent could decrease the effect of the oral contraceptive
Methohexital This product may cause a slight decrease of contraceptive effect
Methylphenobarbital This product may cause a slight decrease of contraceptive effect
Meticillin This anti-infectious agent could decrease the effect of the oral contraceptive
Mezlocillin This anti-infectious agent could decrease the effect of the oral contraceptive
Minocycline This anti-infectious agent could decrease the effect of the oral contraceptive
Modafinil Modafinil decreases the effect of contraceptive
Nafcillin This anti-infectious agent could decrease the effect of the oral contraceptive
Nelfinavir Ritonavir could decrease the contraceptive efficacy
Oxacillin This anti-infectious agent could decrease the effect of the oral contraceptive
Oxcarbazepine Oxcarbazepine decreases the effect of the contracepitve
Oxtriphylline The contraceptive increases the effect and toxicity of theophylline
Oxytetracycline This anti-infectious agent could decrease the effect of the oral contraceptive
Penicillin G This anti-infectious agent could decrease the effect of the oral contraceptive
Penicillin V This anti-infectious agent could decrease the effect of the oral contraceptive
Pentobarbital This product may cause a slight decrease of contraceptive effect
Phenobarbital This product may cause a slight decrease of contraceptive effect
Phenytoin This product may cause a slight decrease of contraceptive effect
Pioglitazone Possible loss of contracepitve effect
Piperacillin This anti-infectious agent could decrease the effect of the oral contraceptive
Pivampicillin This anti-infectious agent could decrease the effect of the oral contraceptive
Prednisolone The estrogenic agent increases the effect of corticosteroid
Prednisone The estrogenic agent increases the effect of corticosteroid
Primidone This product may cause a slight decrease of contraceptive effect
Raloxifene Association not recommended
Rifabutin This product may cause a slight decrease of contraceptive effect
Rifampin This product may cause a slight decrease of contraceptive effect
Rifapentine This product may cause a slight decrease of contraceptive effect
Ritonavir Ritonavir could decrease the contraceptive efficacy
Rolitetracycline This anti-infectious agent could decrease the effect of the oral contraceptive
Secobarbital This product may cause a slight decrease of contraceptive effect
St. John's Wort St. John's Wort could reduce the contraceptive effect
Talbutal This product may cause a slight decrease of contraceptive effect
Tazobactam This anti-infectious agent could decrease the effect of the oral contraceptive
Tetracycline This anti-infectious agent could decrease the effect of the oral contraceptive
Theophylline The contraceptive increases the effect and toxicity of theophylline
Ticarcillin This anti-infectious agent could decrease the effect of the oral contraceptive
Tizanidine The contraceptive increases the effect of tizanidine
Topiramate Topiramate decreases the effect of estrogen
Troglitazone Possible loss of contracepitve effect
Ursodeoxycholic acid Estrogens decreases the effect of ursodiol
Warfarin Increased thrombotic risk due to estrogen
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2A6 (CYP2A6)
  2. Cytochrome P450 3A4 (CYP3A4)
Targets
  1. Estrogen receptor
  2. Orphan nuclear receptor PXR
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2A6 (CYP2A6)
Enzyme 1 Gene Name CYP2A6
Enzyme 1 SwissProt ID P11509 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P11509|CP2A6_HUMAN Cytochrome P450 2A6 (EC 1.14.14.1) 
MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLNTEQMYNSLMK
ISERYGPVFTIHLGPRRVVVLCGHDAVREALVDQAEEFSGRGEQATFDWVFKGYGVVFSN
GERAKQLRRFSIATLRDFGVGKRGIEERIQEEAGFLIDAHRGTGGANIDPTFFLSRTVSN
VISSIVFGDRFDYKDKEFLSLLRMMLGIFQFTSTSTGQLYEMFSSVMKHLPGPQQQAFQL
LQGLEDFIAKKVEHNQRTLDPNSPRDFIDSFLIRMQEEEKNPNTEFYLKNLVMTTLNLFI
GGTETVSTTLRYGFLLLMKHPEVEAKVHEEIDRVIGKNRQPKFEDRAKMPYMEAVIHEIQ
RFGDVIPMSLARRVKKDTKFRDFFLPKGTEVYPMLGSVLRDPSFFSNPQDFNPQHFLNEK
GQFKKSDAFVPFSIGKRNCFGEGLARMELFLFFTTVMQNFRLKSSQSPKDIDVSPKHVGF
ATIPRNYTMSFLPR
Phase 1 Metabolizing Enzyme 2 [top]
Enzyme 2 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 2 Gene Name CYP3A4
Enzyme 2 SwissProt ID P08684 Link Image
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Drug Target 1 [top]
Target 1 ID 136
Target 1 Name Estrogen receptor
Target 1 Synonyms
  1. ER
  2. ER-alpha
  3. Estradiol receptor
Target 1 Gene Name ESR1
Target 1 Protein Sequence >Estrogen receptor 
MTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPAVYNYPEGAAY
EFNAAAAANAQVYGQTGLPYGPGSEAAAFGSNGLGGFPPLNSVSPSPLMLLHPPPQLSPF
LQPHGQQVPYYLENEPSGYTVREAGPPAFYRPNSDNRRQGGRERLASTNDKGSMAMESAK
ETRYCAVCNDYASGYHYGVWSCEGCKAFFKRSIQGHNDYMCPATNQCTIDKNRRKSCQAC
RLRKCYEVGMMKGGIRKDRRGGRMLKHKRQRDDGEGRGEVGSAGDMRAANLWPSPLMIKR
SKKNSLALSLTADQMVSALLDAEPPILYSEYDPTRPFSEASMMGLLTNLADRELVHMINW
AKRVPGFVDLTLHDQVHLLECAWLEILMIGLVWRSMEHPGKLLFAPNLLLDRNQGKCVEG
MVEIFDMLLATSSRFRMMNLQGEEFVCLKSIILLNSGVYTFLSSTLKSLEEKDHIHRVLD
KITDTLIHLMAKAGLTLQQQHQRLAQLLLILSHIRHMSNKGMEHLYSMKCKNVVPLYDLL
LEMLDAHRLHAPTSRGGASVEETDQSHLATAGSTSSHSLQKYYITGEAEGFPATV
Target 1 Number of Residues 604
Target 1 Molecular Weight 66217
Target 1 Theoretical pI 8.14
Target 1 GO Classification
Function
ion binding
cation binding
transition metal ion binding
zinc ion binding
steroid binding
signal transducer activity
receptor activity
ligand-dependent nuclear receptor activity
steroid hormone receptor activity
binding
nucleic acid binding
DNA binding
transcription factor activity
Process
regulation of biological process
regulation of physiological process
regulation of metabolism
regulation of cellular metabolism
regulation of nucleobase, nucleoside, nucleotide and nucleic acid metabolism
regulation of transcription
regulation of transcription, DNA-dependent
Component
organelle
membrane-bound organelle
intracellular membrane-bound organelle
nucleus
Target 1 General Function Involved in transcription factor activity
Target 1 Specific Function Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 31234 Link Image
Target 1 UniProtKB/Swiss-Prot ID P03372 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ESR1_HUMAN Link Image
Target 1 PDB ID 1R5K Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus
Target 1 Gene Sequence >1788 bp 
ATGACCATGACCCTCCACACCAAAGCATCTGGGATGGCCCTACTGCATCAGATCCAAGGG
AACGAGCTGGAGCCCCTGAACCGTCCGCAGCTCAAGATCCCCCTGGAGCGGCCCCTGGGC
GAGGTGTACCTGGACAGCAGCAAGCCCGCCGTGTACAACTACCCCGAGGGCGCCGCCTAC
GAGTTCAACGCCGCGGCCGCCGCCAACGCGCAGGTCTACGGTCAGACCGGCCTCCCCTAC
GGCCCCGGGTCTGAGGCTGCGGCGTTCGGCTCCAACGGCCTGGGGGGTTTCCCCCCACTC
AACAGCGTGTCTCCGAGCCCGCTGATGCTACTGCACCCGCCGCCGCAGCTGTCGCCTTTC
CTGCAGCCCCACGGCCAGCAGGTGCCCTACTACCTGGAGAACGAGCCCAGCGGCTACACG
GTGCGCGAGGCCGGCCCGCCGGCATTCTACAGGCCAAATTCAGATAATCGACGCCAGGGT
GGCAGAGAAAGATTGGCCAGTACCAATGACAAGGGAAGTATGGCTATGGAATCTGCCAAG
GAGACTCGCTACTGTGCAGTGTGCAATGACTATGCTTCAGGCTACCATTATGGAGTCTGG
TCCTGTGAGGGCTGCAAGGCCTTCTTCAAGAGAAGTATTCAAGGACATAACGACTATATG
TGTCCAGCCACCAACCAGTGCACCATTGATAAAAACAGGAGGAAGAGCTGCCAGGCCTGC
CGGCTCCGCAAATGCTACGAAGTGGGAATGATGAAAGGTGGGATACGAAAAGACCGAAGA
GGAGGGAGAATGTTGAAACACAAGCGCCAGAGAGATGATGGGGAGGGCAGGGGTGAAGTG
GGGTCTGCTGGAGACATGAGAGCTGCCAACCTTTGGCCAAGCCCGCTCATGATCAAACGC
TCTAAGAAGAACAGCCTGGCCTTGTCCCTGACGGCCGACCAGATGGTCAGTGCCTTGTTG
GATGCTGAGCCCCCCATACTCTATTCCGAGTATGATCCTACCAGACCCTTCAGTGAAGCT
TCGATGATGGGCTTACTGACCAACCTGGCAGACAGGGAGCTGGTTCACATGATCAACTGG
GCGAAGAGGGTGCCAGGCTTTGTGGATTTGACCCTCCATGATCAGGTCCACCTTCTAGAA
TGTGCCTGGCTAGAGATCCTGATGATTGGTCTCGTCTGGCGCTCCATGGAGCACCCAGTG
AAGCTACTGTTTGCTCCTAACTTGCTCTTGGACAGGAACCAGGGAAAATGTGTAGAGGGC
ATGGTGGAGATCTTCGACATGCTGCTGGCTACATCATCTCGGTTCCGCATGATGAATCTG
CAGGGAGAGGAGTTTGTGTGCCTCAAATCTATTATTTTGCTTAATTCTGGAGTGTACACA
TTTCTGTCCAGCACCCTGAAGTCTCTGGAAGAGAAGGACCATATCCACCGAGTCCTGGAC
AAGATCACAGACACTTTGATCCACCTGATGGCCAAGGCAGGCCTGACCCTGCAGCAGCAG
CACCAGCGGCTGGCCCAGCTCCTCCTCATCCTCTCCCACATCAGGCACATGAGTAACAAA
GGCATGGAGCATCTGTACAGCATGAAGTGCAAGAACGTGGTGCCCCTCTATGACCTGCTG
CTGGAGATGCTGGACGCCCACCGCCTACATGCGCCCACTAGCCGTGGAGGGGCATCCGTG
GAGGAGACGGACCAAAGCCACTTGGCCACTGCGGGCTCTACTTCATCGCATTCCTTGCAA
AAGTATTACATCACGGGGGAGGCAGAGGGTTTCCCTGCCACAGTCTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID ESR1 Link Image
Target 1 GenAtlas ID ESR1 Link Image
Target 1 HGNC ID HGNC:3467 Link Image
Target 1 Chromosome Location 6
Target 1 Locus 6q25.1
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Montano MM, Ekena K, Delage-Mourroux R, Chang W, Martini P, Katzenellenbogen BS: An estrogen receptor-selective coregulator that potentiates the effectiveness of antiestrogens and represses the activity of estrogens. Proc Natl Acad Sci U S A. 1999 Jun 8;96(12):6947-52. [PubMed Link Image]
  2. Rogatsky I, Trowbridge JM, Garabedian MJ: Potentiation of human estrogen receptor alpha transcriptional activation through phosphorylation of serines 104 and 106 by the cyclin A-CDK2 complex. J Biol Chem. 1999 Aug 6;274(32):22296-302. [PubMed Link Image]
  3. Lee SK, Anzick SL, Choi JE, Bubendorf L, Guan XY, Jung YK, Kallioniemi OP, Kononen J, Trent JM, Azorsa D, Jhun BH, Cheong JH, Lee YC, Meltzer PS, Lee JW: A nuclear factor, ASC-2, as a cancer-amplified transcriptional coactivator essential for ligand-dependent transactivation by nuclear receptors in vivo. J Biol Chem. 1999 Nov 26;274(48):34283-93. [PubMed Link Image]
  4. Schubert EL, Lee MK, Newman B, King MC: Single nucleotide polymorphisms (SNPs) in the estrogen receptor gene and breast cancer susceptibility. J Steroid Biochem Mol Biol. 1999 Nov;71(1-2):21-7. [PubMed Link Image]
  5. Sauve F, McBroom LD, Gallant J, Moraitis AN, Labrie F, Giguere V: CIA, a novel estrogen receptor coactivator with a bifunctional nuclear receptor interacting determinant. Mol Cell Biol. 2001 Jan;21(1):343-53. [PubMed Link Image]
  6. Shao W, Halachmi S, Brown M: ERAP140, a conserved tissue-specific nuclear receptor coactivator. Mol Cell Biol. 2002 May;22(10):3358-72. [PubMed Link Image]
  7. Wong CW, McNally C, Nickbarg E, Komm BS, Cheskis BJ: Estrogen receptor-interacting protein that modulates its nongenomic activity-crosstalk with Src/Erk phosphorylation cascade. Proc Natl Acad Sci U S A. 2002 Nov 12;99(23):14783-8. Epub 2002 Nov 1. [PubMed Link Image]
  8. Mungall AJ, Palmer SA, Sims SK, Edwards CA, Ashurst JL, Wilming L, Jones MC, Horton R, Hunt SE, Scott CE, Gilbert JG, Clamp ME, Bethel G, Milne S, Ainscough R, Almeida JP, Ambrose KD, Andrews TD, Ashwell RI, Babbage AK, Bagguley CL, Bailey J, Banerjee R, Barker DJ, Barlow KF, Bates K, Beare DM, Beasley H, Beasley O, Bird CP, Blakey S, Bray-Allen S, Brook J, Brown AJ, Brown JY, Burford DC, Burrill W, Burton J, Carder C, Carter NP, Chapman JC, Clark SY, Clark G, Clee CM, Clegg S, Cobley V, Collier RE, Collins JE, Colman LK, Corby NR, Coville GJ, Culley KM, Dhami P, Davies J, Dunn M, Earthrowl ME, Ellington AE, Evans KA, Faulkner L, Francis MD, Frankish A, Frankland J, French L, Garner P, Garnett J, Ghori MJ, Gilby LM, Gillson CJ, Glithero RJ, Grafham DV, Grant M, Gribble S, Griffiths C, Griffiths M, Hall R, Halls KS, Hammond S, Harley JL, Hart EA, Heath PD, Heathcott R, Holmes SJ, Howden PJ, Howe KL, Howell GR, Huckle E, Humphray SJ, Humphries MD, Hunt AR, Johnson CM, Joy AA, Kay M, Keenan SJ, Kimberley AM, King A, Laird GK, Langford C, Lawlor S, Leongamornlert DA, Leversha M, Lloyd CR, Lloyd DM, Loveland JE, Lovell J, Martin S, Mashreghi-Mohammadi M, Maslen GL, Matthews L, McCann OT, McLaren SJ, McLay K, McMurray A, Moore MJ, Mullikin JC, Niblett D, Nickerson T, Novik KL, Oliver K, Overton-Larty EK, Parker A, Patel R, Pearce AV, Peck AI, Phillimore B, Phillips S, Plumb RW, Porter KM, Ramsey Y, Ranby SA, Rice CM, Ross MT, Searle SM, Sehra HK, Sheridan E, Skuce CD, Smith S, Smith M, Spraggon L, Squares SL, Steward CA, Sycamore N, Tamlyn-Hall G, Tester J, Theaker AJ, Thomas DW, Thorpe A, Tracey A, Tromans A, Tubby B, Wall M, Wallis JM, West AP, White SS, Whitehead SL, Whittaker H, Wild A, Willey DJ, Wilmer TE, Wood JM, Wray PW, Wyatt JC, Young L, Younger RM, Bentley DR, Coulson A, Durbin R, Hubbard T, Sulston JE, Dunham I, Rogers J, Beck S: The DNA sequence and analysis of human chromosome 6. Nature. 2003 Oct 23;425(6960):805-11. [PubMed Link Image]
  9. Reese JC, Katzenellenbogen BS: Characterization of a temperature-sensitive mutation in the hormone binding domain of the human estrogen receptor. Studies in cell extracts and intact cells and their implications for hormone-dependent transcriptional activation. J Biol Chem. 1992 May 15;267(14):9868-73. [PubMed Link Image]
  10. Schwabe JW, Neuhaus D, Rhodes D: Solution structure of the DNA-binding domain of the oestrogen receptor. Nature. 1990 Nov 29;348(6300):458-61. [PubMed Link Image]
  11. 2792078 Tora L, Mullick A, Metzger D, Ponglikitmongkol M, Park I, Chambon P: The cloned human oestrogen receptor contains a mutation which alters its hormone binding properties. EMBO J. 1989 Jul;8(7):1981-6.
  12. 3753802 Greene GL, Gilna P, Waterfield M, Baker A, Hort Y, Shine J: Sequence and expression of human estrogen receptor complementary DNA. Science. 1986 Mar 7;231(4742):1150-4.
  13. 3754034 Green S, Walter P, Kumar V, Krust A, Bornert JM, Argos P, Chambon P: Human oestrogen receptor cDNA: sequence, expression and homology to v-erb-A. Nature. 1986 Mar 13-19;320(6058):134-9.
  14. 7476978 Joel PB, Traish AM, Lannigan DA: Estradiol and phorbol ester cause phosphorylation of serine 118 in the human estrogen receptor. Mol Endocrinol. 1995 Aug;9(8):1041-52.
  15. 7539106 Arnold SF, Obourn JD, Jaffe H, Notides AC: Phosphorylation of the human estrogen receptor on tyrosine 537 in vivo and by src family tyrosine kinases in vitro. Mol Endocrinol. 1995 Jan;9(1):24-33.
  16. 7838153 Arnold SF, Obourn JD, Jaffe H, Notides AC: Serine 167 is the major estradiol-induced phosphorylation site on the human estrogen receptor. Mol Endocrinol. 1994 Sep;8(9):1208-14.
  17. 7916651 Pfeffer U, Fecarotta E, Castagnetta L, Vidali G: Estrogen receptor variant messenger RNA lacking exon 4 in estrogen-responsive human breast cancer cell lines. Cancer Res. 1993 Feb 15;53(4):741-3.
  18. 8221895 Schwabe JW, Chapman L, Finch JT, Rhodes D: The crystal structure of the estrogen receptor DNA-binding domain bound to DNA: how receptors discriminate between their response elements. Cell. 1993 Nov 5;75(3):567-78.
  19. 8600466 Pink JJ, Wu SQ, Wolf DM, Bilimoria MM, Jordan VC: A novel 80 kDa human estrogen receptor containing a duplication of exons 6 and 7. Nucleic Acids Res. 1996 Mar 1;24(5):962-9.
  20. 8961262 McInerney EM, Ince BA, Shapiro DJ, Katzenellenbogen BS: A transcriptionally active estrogen receptor mutant is a novel type of dominant negative inhibitor of estrogen action. Mol Endocrinol. 1996 Dec;10(12):1519-26.
  21. 9195227 Anderson TI, Wooster R, Laake K, Collins N, Warren W, Skrede M, Elles R, Tveit KM, Johnston SR, Dowsett M, Olsen AO, Moller P, Stratton MR, Borresen-Dale AL: Screening for ESR mutations in breast and ovarian cancer patients. Hum Mutat. 1997;9(6):531-6.
  22. 9338790 Brzozowski AM, Pike AC, Dauter Z, Hubbard RE, Bonn T, Engstrom O, Ohman L, Greene GL, Gustafsson JA, Carlquist M: Molecular basis of agonism and antagonism in the oestrogen receptor. Nature. 1997 Oct 16;389(6652):753-8.
  23. 9600906 Tanenbaum DM, Wang Y, Williams SP, Sigler PB: Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains. Proc Natl Acad Sci U S A. 1998 May 26;95(11):5998-6003.
  24. 9619507 Maalouf GJ, Xu W, Smith TF, Mohr SC: Homology model for the ligand-binding domain of the human estrogen receptor. J Biomol Struct Dyn. 1998 Apr;15(5):841-51.
  25. 9875847 Shiau AK, Barstad D, Loria PM, Cheng L, Kushner PJ, Agard DA, Greene GL: The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell. 1998 Dec 23;95(7):927-37.
Target 1 Drug References
  1. Micevych PE, Chaban V, Ogi J, Dewing P, Lu JK, Sinchak K: Estradiol stimulates progesterone synthesis in hypothalamic astrocyte cultures. Endocrinology. 2007 Feb;148(2):782-9. Epub 2006 Nov 9. [PubMed Link Image]
  2. Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. [PubMed Link Image]
  3. Brama M, Gnessi L, Basciani S, Cerulli N, Politi L, Spera G, Mariani S, Cherubini S, d'Abusco AS, Scandurra R, Migliaccio S: Cadmium induces mitogenic signaling in breast cancer cell by an ERalpha-dependent mechanism. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):102-8. Epub 2006 Nov 27. [PubMed Link Image]
  4. Lehnes K, Winder AD, Alfonso C, Kasid N, Simoneaux M, Summe H, Morgan E, Iann MC, Duncan J, Eagan M, Tavaluc R, Evans CH Jr, Russell R, Wang A, Hu F, Stoica A: The effect of estradiol on in vivo tumorigenesis is modulated by the human epidermal growth factor receptor 2/phosphatidylinositol 3-kinase/Akt1 pathway. Endocrinology. 2007 Mar;148(3):1171-80. Epub 2006 Nov 30. [PubMed Link Image]
  5. Mukai H, Tsurugizawa T, Ogiue-Ikeda M, Murakami G, Hojo Y, Ishii H, Kimoto T, Kawato S: Local neurosteroid production in the hippocampus: influence on synaptic plasticity of memory. Neuroendocrinology. 2006;84(4):255-63. Epub 2006 Dec 1. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 1284
Target 2 Name Orphan nuclear receptor PXR
Target 2 Synonyms
  1. Orphan nuclear receptor PAR1
  2. Pregnane X receptor
  3. SXR
  4. Steroid and xenobiotic receptor
Target 2 Gene Name NR1I2
Target 2 Protein Sequence >Orphan nuclear receptor PXR 
MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATGYHFNVMTCEG
CKGFFRRAMKRNARLRCPFRKGACEITRKTRRQCQACRLRKCLESGMKKEMIMSDEAVEE
RRALIKRKKSERTGTQPLGVQGLTEEQRMMIRELMDAQMKTFDTTFSHFKNFRLPGVLSS
GCELPESLQAPSREEAAKWSQVRKDLCSLKVSLQLRGEDGSVWNYKPPADSGGKEIFSLL
PHMADMSTYMFKGIISFAKVISYFRDLPIEDQISLLKGAAFELCQLRFNTVFNAETGTWE
CGRLSYCLEDTAGGFQQLLLEPMLKFHYMLKKLQLHEEEYVLMQAISLFSPDRPGVLQHR
VVDQLQEQFAITLKSYIECNRPQPAHRFLFLKIMAMLTELRSINAQHTQRLLRIQDIHPF
ATPLMQELFGITGS
Target 2 Number of Residues 441
Target 2 Molecular Weight 49762
Target 2 Theoretical pI 8.44
Target 2 GO Classification
Function
signal transducer activity
receptor activity
ligand-dependent nuclear receptor activity
steroid hormone receptor activity
binding
nucleic acid binding
DNA binding
transcription factor activity
Process
regulation of biological process
regulation of physiological process
regulation of metabolism
regulation of cellular metabolism
regulation of nucleobase, nucleoside, nucleotide and nucleic acid metabolism
regulation of transcription
regulation of transcription, DNA-dependent
Component
organelle
membrane-bound organelle
intracellular membrane-bound organelle
nucleus
Target 2 General Function Involved in transcription factor activity
Target 2 Specific Function Orphan receptor; its natural ligand is probably pregnane. Binds to a response element in the CYP3A4 and ABCB1/MDR1 genes promoter. Activates its expression in response to a wide variety of endobiotics and xenobiotics
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 3511138 Link Image
Target 2 UniProtKB/Swiss-Prot ID O75469 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name PXR_HUMAN Link Image
Target 2 PDB ID 1NRL Link Image
Target 2 PDB File Show
Target 2 3D Structure
Target 2 Cellular Location
  • Nucleus
Target 2 Gene Sequence >1305 bp 
CTGGAGGTGAGACCCAAAGAAAGCTGGAACCATGCTGACTTTGTACACTGTGAGGACACA
GAGTCTGTTCCTGGAAAGCCCAGTGTCAACGCAGATGAGGAAGTCGGAGGTCCCCAAATC
TGCCGTGTATGTGGGGACAAGGCCACTGGCTATCACTTCAATGTCATGACATGTGAAGGA
TGCAAGGGCTTTTTCAGGAGGGCCATGAAACGCAACGCCCGGCTGAGGTGCCCCTTCCGG
AAGGGCGCCTGCGAGATCACCCGGAAGACCCGGCGACAGTGCCAGGCCTGCCGCCTGCGC
AAGTGCCTGGAGAGCGGCATGAAGAAGGAGATGATCATGTCCGACGAGGCCGTGGAGGAG
AGGCGGGCCTTGATCAAGCGGAAGAAAAGTGAACGGACAGGGACTCAGCCACTGGGAGTG
CAGGGGCTGACAGAGGAGCAGCGGATGATGATCAGGGAGCTGATGGACGCTCAGATGAAA
ACCTTTGACACTACCTTCTCCCATTTCAAGAATTTCCGGCTGCCAGGGGTGCTTAGCAGT
GGCTGCGAGTTGCCAGAGTCTCTGCAGGCCCCATCGAGGGAAGAAGCTGCCAAGTGGAGC
CAGGTCCGGAAAGATCTGTGCTCTTTGAAGGTCTCTCTGCAGCTGCGGGGGGAGGATGGC
AGTGTCTGGAACTACAAACCCCCAGCCGACAGTGGCGGGAAAGAGATCTTCTCCCTGCTG
CCCCACATGGCTGACATGTCAACCTACATGTTCAAAGGCATCATCAGCTTTGCCAAAGTC
ATCTCCTACTTCAGGGACTTGCCCATCGAGGACCAGATCTCCCTGCTGAAGGGGGCCGCT
TTCGAGCTGTGTCAACTGAGATTCAACACAGTGTTCAACGCGGAGACTGGAACCTGGGAG
TGTGGCCGGCTGTCCTACTGCTTGGAAGACACTGCAGGTGGCTTCCAGCAACTTCTACTG
GAGCCCATGCTGAAATTCCACTACATGCTGAAGAAGCTGCAGCTGCATGAGGAGGAGTAT
GTGCTGATGCAGGCCATCTCCCTCTTCTCCCCAGACCGCCCAGGTGTGCTGCAGCACCGC
GTGGTGGACCAGCTGCAGGAGCAATTCGCCATTACTCTGAAGTCCTACATTGAATGCAAT
CGGCCCCAGCCTGCTCATAGGTTCTTGTTCCTGAAGATCATGGCTATGCTCACCGAGCTC
CGCAGCATCAATGCTCAGCACACCCAGCGGCTGCTGCGCATCCAGGACATACACCCCTTT
GCTACGCCCCTCATGCAGGAGTTGTTCGGCATCACAGGTAGCTGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID NR1I2 Link Image
Target 2 GenAtlas ID NR1I2 Link Image
Target 2 HGNC ID HGNC:7968 Link Image
Target 2 Chromosome Location 3
Target 2 Locus 3q12-q13.3
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Watkins RE, Wisely GB, Moore LB, Collins JL, Lambert MH, Williams SP, Willson TM, Kliewer SA, Redinbo MR: The human nuclear xenobiotic receptor PXR: structural determinants of directed promiscuity. Science. 2001 Jun 22;292(5525):2329-33. Epub 2001 Jun 14. [PubMed Link Image]
  2. Zhang J, Kuehl P, Green ED, Touchman JW, Watkins PB, Daly A, Hall SD, Maurel P, Relling M, Brimer C, Yasuda K, Wrighton SA, Hancock M, Kim RB, Strom S, Thummel K, Russell CG, Hudson JR Jr, Schuetz EG, Boguski MS: The human pregnane X receptor: genomic structure and identification and functional characterization of natural allelic variants. Pharmacogenetics. 2001 Oct;11(7):555-72. [PubMed Link Image]
  3. Kawana K, Ikuta T, Kobayashi Y, Gotoh O, Takeda K, Kawajiri K: Molecular mechanism of nuclear translocation of an orphan nuclear receptor, SXR. Mol Pharmacol. 2003 Mar;63(3):524-31. [PubMed Link Image]
  4. Lehmann JM, McKee DD, Watson MA, Willson TM, Moore JT, Kliewer SA: The human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions. J Clin Invest. 1998 Sep 1;102(5):1016-23. [PubMed Link Image]
  5. Bertilsson G, Heidrich J, Svensson K, Asman M, Jendeberg L, Sydow-Backman M, Ohlsson R, Postlind H, Blomquist P, Berkenstam A: Identification of a human nuclear receptor defines a new signaling pathway for CYP3A induction. Proc Natl Acad Sci U S A. 1998 Oct 13;95(21):12208-13. [PubMed Link Image]
  6. Blumberg B, Sabbagh W Jr, Juguilon H, Bolado J Jr, van Meter CM, Ong ES, Evans RM: SXR, a novel steroid and xenobiotic-sensing nuclear receptor. Genes Dev. 1998 Oct 15;12(20):3195-205. [PubMed Link Image]
Target 2 Drug References
  1. Xue Y, Moore LB, Orans J, Peng L, Bencharit S, Kliewer SA, Redinbo MR: Crystal structure of the pregnane X receptor-estradiol complex provides insights into endobiotic recognition. Mol Endocrinol. 2007 May;21(5):1028-38. Epub 2007 Feb 27. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.