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Human Metabolome Database Version 2.5

 

Showing metabocard for 17a-Ethynylestradiol (HMDB01926)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-18 09:38:06
Update Date 2009-05-05 20:59:02
Accession Number HMDB01926
Secondary Accession Numbers Not Available
Common Name 17a-Ethynylestradiol
Description Ethinyl estradiol 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; estradiol (17-beta estradiol) (also oestradiol) is a sex hormone. Labelled the "female" hormone but also present in males it represents the major estrogen in humans. Critical for sexual functioning, estradiol also supports bone growth. -- Wikipedia; One of the fascinating twists to mammalian sexual differentiation is that estradiol is one of the two active metabolites of testosterone in males (the other being dihydrotestosterone). estradiol cannot be transferred readily from the circulation into the brain. Since fetuses of both sexes are exposed to similarly high levels of maternal estradiol, it can play little role in prenatal sexual differentiation. However, testosterone enters the central nervous system more freely and significant amounts are aromatized to estradiol within the brain of most male mammals, including humans. There is now much evidence that the programming of adult male sexual behavior in "lower mammals," (such as mounting rather than lordosis behavior), is largely dependent on estradiol produced in the central nervous system during prenatal life and early infancy from testosterone. We do not yet know whether this process plays a minimal or significant part in human sexual behaviors. -- Wikipedia; A synthetic form of estradiol, called ethinyl estradiol is a major component of hormonal contraceptive devices. Combined oral contraceptives contain ethinyl estradiol and a progestin, which both contribute to the inhibition of GnRH, LH, and FSH. The inhibition of these hormones accounts for the ability of combined oral contraceptives or birth control pills to prevent ovulation and thus prevent pregnancy. Other types of hormonal birth control contain only progestins and no ethinyl estradiol. -- Wikipedia
Synonyms
  1. 17-Ethinyl-3,17-estradiol
  2. 17-Ethinyl-3,17-oestradiol
  3. 17-Ethinylestradiol
  4. 17-Ethynylestradiol
  5. 17-Ethynylestradiol ram
  6. 17-Ethynyloestradiol
  7. 17a-Ethinyl-17b-estradiol
  8. 17a-Ethinylestradiol
  9. 17a-Ethynyl-17b-oestradiol
  10. 17a-Ethynylestradiol-l7b
  11. 17a-Ethynyloestradiol
  12. 17a-Ethynyloestradiol-17b
  13. 17alpha-Ethinyl estradiol
  14. Alora
  15. Amenoron
  16. Anovlar
  17. Chee-O-Gen
  18. Chee-O-Genf
  19. Diognat-E
  20. Diogyn E
  21. Diogyn-E
  22. Dyloform
  23. Ertonyl
  24. Esclim
  25. Esteed
  26. Estigyn
  27. Estinyl
  28. Eston-E
  29. Estoral
  30. Estoral {[Orion]}
  31. Estorals
  32. Estring
  33. Estrogen
  34. Ethidol
  35. Ethinoral
  36. Ethinylestriol
  37. Ethinyloestradiol
  38. Ethynylestradiol
  39. Eticyclin
  40. Eticyclol
  41. Eticylol
  42. Etinestrol
  43. Etinestryl
  44. Etinoestryl
  45. Etistradiol
  46. Etivex
  47. Feminone
  48. Fempatch
  49. Follicoral
  50. Ginestrene
  51. Gynodiol
  52. Gynolett
  53. Inestra
  54. Innofem
  55. Kolpolyn
  56. Linoral
  57. Lynoral
  58. Menolyn
  59. Menostar
  60. Neo-Estrone
  61. Nogest-S
  62. Novestrol
  63. Oradiol
  64. Orestralyn
  65. Orestrayln
  66. Ovex
  67. Palonyl
  68. Perovex
  69. Primogyn
  70. Primogyn C
  71. Primogyn M
  72. Progynon C
  73. Progynon M
  74. Spanestrin
  75. Thiuram E
  76. Thiuranide
  77. Vagifem
  78. Ylestrol
  79. ethinyl estradiol
Chemical IUPAC Name 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
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Drug
Species
  • tertiary alcohol
  • phenol or hydroxyhetarene
  • alkyne
  • aromatic compound
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Exogenous
Average Molecular Weight 296.403
Monoisotopic Molecular Weight 296.177643
Isomeric SMILES C[C@]12CC[C@H]3[C@@H](CCC4=CC(O)=CC=C34)[C@@H]1CC[C@@]2(O)C#C
Canonical SMILES CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2(O)C#C
KEGG Compound ID C07534 Link Image
BioCyc ID --ABIETADIENE Link Image
BiGG ID Not Available
Wikipedia Link Alora Link Image
NuGOwiki Link HMDB01926 Link Image
Metagene Link HMDB01926 Link Image
METLIN ID 6392 Link Image
PubChem Compound 3285 Link Image
PubChem Substance 9401161 Link Image
ChEBI ID 4903 Link Image
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
Synthesis Reference Not Available
Melting Point (Experimental) 183 oC
Experimental Water Solubility 0.0113 mg/mL at 27 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 6.77e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 3.67 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 7.49 [Predicted by PubChem via XLOGP]; 3.63 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Blood
Tissue Location
Tissue References
Adipose Tissue —
Adrenal Cortex —
Adrenal Gland —
Bladder —
Brain —
Epidermis —
Fibroblasts —
Gonads —
Intestine —
Kidney —
Muscle —
Nerve Cells —
Neuron —
Pancreas —
Placenta —
Platelet —
Prostate —
Skeletal Muscle —
Spleen —
Stratum Corneum —
Testes —
Thyroid Gland —
Concentrations (Normal)
Biofluid Blood
Value 0.00016 (0.000084-0.00027) uM
Age Adult:>18 yrs old
Sex Both
Patient information In oral contraceptive users
Comments Not Available
References
  • Stanczyk FZ, Ploszaj S, Gentzschein E, Qian D, Mishell DR Jr: Effect of oral contraceptives containing 20 and 35 micrograms ethinyl estradiol on urinary prostacyclin and thromboxane metabolite levels in smokers and nonsmokers. Contraception. 1999 Jan;59(1):17-23. [PubMed Link Image]
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways Not Available
General References
  1. Li X, Strauss L, Kaatrasalo A, Mayerhofer A, Huhtaniemi I, Santti R, Makela S, Poutanen M: Transgenic mice expressing p450 aromatase as a model for male infertility associated with chronic inflammation in the testis. Endocrinology. 2006 Mar;147(3):1271-7. Epub 2005 Nov 23. [PubMed Link Image]
  2. Wernert N: [Immunohistochemistry of the prostate and prostate carcinomas] Veroff Pathol. 1991;135:1-163. [PubMed Link Image]
  3. Kaufer D, Ogle WO, Pincus ZS, Clark KL, Nicholas AC, Dinkel KM, Dumas TC, Ferguson D, Lee AL, Winters MA, Sapolsky RM: Restructuring the neuronal stress response with anti-glucocorticoid gene delivery. Nat Neurosci. 2004 Sep;7(9):947-53. Epub 2004 Aug 8. [PubMed Link Image]
  4. Zhang L, Sukhareva M, Barker JL, Maric D, Hao Y, Chang YH, Ma W, O'Shaughnessy T, Rubinow DR: Direct binding of estradiol enhances Slack (sequence like a calcium-activated potassium channel) channels' activity. Neuroscience. 2005;131(2):275-82. [PubMed Link Image]
  5. Herrero P, Soto PF, Dence CS, Kisrieva-Ware Z, Delano DA, Peterson LR, Gropler RJ: Impact of hormone replacement on myocardial fatty acid metabolism: potential role of estrogen. J Nucl Cardiol. 2005 Sep-Oct;12(5):574-81. [PubMed Link Image]
  6. Shah MG, Maibach HI: Estrogen and skin. An overview. Am J Clin Dermatol. 2001;2(3):143-50. [PubMed Link Image]
  7. Safi R, Kovacic A, Gaillard S, Murata Y, Simpson ER, McDonnell DP, Clyne CD: Coactivation of liver receptor homologue-1 by peroxisome proliferator-activated receptor gamma coactivator-1alpha on aromatase promoter II and its inhibition by activated retinoid X receptor suggest a novel target for breast-specific antiestrogen therapy. Cancer Res. 2005 Dec 15;65(24):11762-70. [PubMed Link Image]
  8. vom Saal FS, Grant WM, McMullen CW, Laves KS: High fetal estrogen concentrations: correlation with increased adult sexual activity and decreased aggression in male mice. Science. 1983 Jun 17;220(4603):1306-9. [PubMed Link Image]
  9. Schmitt PM, Gohil K, Kaufman MP: Spinal estrogen attenuates the exercise pressor reflex but has little effect on the expression of genes regulating neurotransmitters in the dorsal root ganglia. J Appl Physiol. 2006 Mar;100(3):958-64. Epub 2005 Nov 23. [PubMed Link Image]
  10. Kalaitzidis D, Ok J, Sulak L 2nd, Starczynowski DT, Gilmore TD: Characterization of a human REL-estrogen receptor fusion protein with a reverse conditional transforming activity in chicken spleen cells. Oncogene. 2004 Sep 30;23(45):7580-7. [PubMed Link Image]
  11. Pierard-Franchimont C, Letawe C, Goffin V, Pierard GE: Skin water-holding capacity and transdermal estrogen therapy for menopause: a pilot study. Maturitas. 1995 Sep;22(2):151-4. [PubMed Link Image]
  12. de la Monte SM, Moore GW, Hutchins GM: Metastatic behavior of prostate cancer. Cluster analysis of patterns with respect to estrogen treatment. Cancer. 1986 Aug 15;58(4):985-93. [PubMed Link Image]
  13. Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [PubMed Link Image]
  14. Harris H, Henderson R, Bhat R, Komm B: Regulation of metallothionein II messenger ribonucleic acid measures exogenous estrogen receptor-beta activity in SAOS-2 and LNCaPLN3 cells. Endocrinology. 2001 Feb;142(2):645-52. [PubMed Link Image]
  15. Stabile LP, Davis AL, Gubish CT, Hopkins TM, Luketich JD, Christie N, Finkelstein S, Siegfried JM: Human non-small cell lung tumors and cells derived from normal lung express both estrogen receptor alpha and beta and show biological responses to estrogen. Cancer Res. 2002 Apr 1;62(7):2141-50. [PubMed Link Image]
  16. Frolich A, Christensen L, Andersen J: Estrogen receptors appear undetectable in the C-cells of the human thyroid gland. Bone. 1990;11(6):393-6. [PubMed Link Image]
  17. Siiteri PK: Review of studies on estrogen biosynthesis in the human. Cancer Res. 1982 Aug;42(8 Suppl):3269s-3273s. [PubMed Link Image]
  18. Koehler KF, Helguero LA, Haldosen LA, Warner M, Gustafsson JA: Reflections on the discovery and significance of estrogen receptor beta. Endocr Rev. 2005 May;26(3):465-78. Epub 2005 Apr 27. [PubMed Link Image]
  19. Moro L, Reineri S, Piranda D, Pietrapiana D, Lova P, Bertoni A, Graziani A, Defilippi P, Canobbio I, Torti M, Sinigaglia F: Nongenomic effects of 17beta-estradiol in human platelets: potentiation of thrombin-induced aggregation through estrogen receptor beta and Src kinase. Blood. 2005 Jan 1;105(1):115-21. Epub 2004 Jun 15. [PubMed Link Image]
  20. Nakano Y, Oshima T, Ozono R, Ueda A, Oue Y, Matsuura H, Sanada M, Ohama K, Chayama K, Kambe M: Estrogen replacement suppresses function of thrombin stimulated platelets by inhibiting Ca(2+) influx and raising cyclic adenosine monophosphate. Cardiovasc Res. 2002 Feb 15;53(3):634-41. [PubMed Link Image]
  21. Wikipedia Link Image