Estetrol (BioDeep_00000858561)

Main id: BioDeep_00000229484

Secondary id: BioDeep_00000178806

PANOMIX_OTCML-2023


代谢物信息卡片


Estetrol

化学式: C18H24O4 (304.1674504)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.54%

分子结构信息

SMILES: CC12CCC3C(C1C(C(C2O)O)O)CCC4=C3C=CC(=C4)O
InChI: InChI=1S/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/m1/s1

描述信息

A 3-hydroxy steroid that is 17beta-estradiol which has been substituted at the 15alpha and 16alpha positions by two additional hydroxy groups. It is a natural estrogen produced exclusively during pregnancy by the fetal liver.
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
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Estetrol, a natural estrogen synthesized exclusively during pregnancy by the human fetal liver, is a selective nuclear estrogen receptor modulator. Estetrol exerts estrogenic actions on the endometrium or the central nervous system but presents antagonistic effects on the breast[1][2].

同义名列表

1 个代谢物同义名

Estetrol



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Franca Fruzzetti, Tiziana Fidecicchi, Marco Gambacciani. Oestrogens in oral contraception: considerations for tailoring prescription to women's needs. The European journal of contraception & reproductive health care : the official journal of the European Society of Contraception. 2024 Jun; 29(3):93-102. doi: 10.1080/13625187.2024.2334350. [PMID: 38683756]
  • Ana Sofia Zabala, Rocío Ayelem Conforti, María Belén Delsouc, Verónica Filippa, Maria Magdalena Montt-Guevara, Andrea Giannini, Tommaso Simoncini, Sandra Silvina Vallcaneras, Marilina Casais. Estetrol Inhibits Endometriosis Development in an In Vivo Murine Model. Biomolecules. 2024 May; 14(5):. doi: 10.3390/biom14050580. [PMID: 38785987]
  • Kristina Gemzell-Danielsson, Angelo Cagnacci, Nathalie Chabbert-Buffet, Jonathan Douxfils, Jean-Michel Foidart, Ali Kubba, Luis Ignacio Lete Lasa, Diana Mansour, Joseph Neulen, Jaoquim Neves, Fátima Palma, Thomas Römer, Robert Spaczyński, Vera Tóth. A novel estetrol-containing combined oral contraceptive: European expert panel review. The European journal of contraception & reproductive health care : the official journal of the European Society of Contraception. 2022 Oct; 27(5):373-383. doi: 10.1080/13625187.2022.2093850. [PMID: 35862627]
  • Arnold Lee, Yahiya Y Syed. Estetrol/Drospirenone: A Review in Oral Contraception. Drugs. 2022 Jul; 82(10):1117-1125. doi: 10.1007/s40265-022-01738-8. [PMID: 35781795]
  • Kristina Gemzell-Danielsson, Angelo Cagnacci, Nathalie Chabbert-Buffet, Jonathan Douxfils, Jean-Michel Foidart, Ali Kubba, Luis Ignacio Lete Lasa, Diana Mansour, Joseph Neulen, Jaoquim Neves, Fátima Palma, Thomas Römer, Robert Spaczy Ski, Vera Tóth. A novel estetrol-containing combined oral contraceptive: European expert panel review. Ceska gynekologie. 2022; 87(6):440-452. doi: 10.1080/ 13625187.2022.2093850. [PMID: 36543594]
  • David M Paton. Estetrol and drospirenone: a novel oral contraceptive. Drugs of today (Barcelona, Spain : 1998). 2022 Jan; 58(1):1-8. doi: 10.1358/dot.2022.58.1.3353167. [PMID: 35107089]
  • Ingrid Duijkers, Christine Klipping, Virginie Kinet, Maud Jost, Adriana Bastidas, Jean-Michel Foidart. Effects of an oral contraceptive containing estetrol and drospirenone on ovarian function. Contraception. 2021 06; 103(6):386-393. doi: 10.1016/j.contraception.2021.03.003. [PMID: 33689786]
  • Christine Klipping, Ingrid Duijkers, Marie Mawet, Catherine Maillard, Adriana Bastidas, Maud Jost, Jean-Michel Foidart. Endocrine and metabolic effects of an oral contraceptive containing estetrol and drospirenone. Contraception. 2021 04; 103(4):213-221. doi: 10.1016/j.contraception.2021.01.001. [PMID: 33428907]
  • Herjan J T Coelingh Bennink, Yvette Zimmerman, Carole Verhoeven, Alice E Dutman, Tjeert Mensinga, Cornelis Kluft, Yacov Reisman, Frans M J Debruyne. A Dose-Escalating Study With the Fetal Estrogen Estetrol in Healthy Men. The Journal of clinical endocrinology and metabolism. 2018 09; 103(9):3239-3249. doi: 10.1210/jc.2018-00147. [PMID: 29931320]
  • Emmanuel Guivarc'h, Mélissa Buscato, Anne-Laure Guihot, Julie Favre, Emilie Vessières, Linda Grimaud, Jamal Wakim, Nada-Joe Melhem, Rana Zahreddine, Marine Adlanmerini, Laurent Loufrani, Claude Knauf, John A Katzenellenbogen, Benita S Katzenellenbogen, Jean-Michel Foidart, Pierre Gourdy, Françoise Lenfant, Jean-François Arnal, Daniel Henrion, Coralie Fontaine. Predominant Role of Nuclear Versus Membrane Estrogen Receptor α in Arterial Protection: Implications for Estrogen Receptor α Modulation in Cardiovascular Prevention/Safety. Journal of the American Heart Association. 2018 06; 7(13):. doi: 10.1161/jaha.118.008950. [PMID: 29959137]
  • H J T Coelingh Bennink, C Verhoeven, Y Zimmerman, M Visser, J-M Foidart, K Gemzell-Danielsson. Pharmacokinetics of the fetal estrogen estetrol in a multiple-rising-dose study in postmenopausal women. Climacteric : the journal of the International Menopause Society. 2017 Jun; 20(3):285-289. doi: 10.1080/13697137.2017.1291608. [PMID: 28267365]
  • Cornelis Kluft, Yvette Zimmerman, Marie Mawet, Christine Klipping, Ingrid J M Duijkers, Jacoline Neuteboom, Jean-Michel Foidart, Herjan Coelingh Bennink. Reduced hemostatic effects with drospirenone-based oral contraceptives containing estetrol vs. ethinyl estradiol. Contraception. 2017 Feb; 95(2):140-147. doi: 10.1016/j.contraception.2016.08.018. [PMID: 27593335]
  • N Pluchino, P Drakopoulos, E Casarosa, L Freschi, P Petignat, M Yaron, A R Genazzani. Effect of estetrol on Beta-Endorphin level in female rats. Steroids. 2015 Mar; 95(?):104-10. doi: 10.1016/j.steroids.2015.01.003. [PMID: 25595451]
  • Marie Mawet, Catherine Maillard, Christine Klipping, Yvette Zimmerman, Jean-Michel Foidart, Herjan J T Coelingh Bennink. Unique effects on hepatic function, lipid metabolism, bone and growth endocrine parameters of estetrol in combined oral contraceptives. The European journal of contraception & reproductive health care : the official journal of the European Society of Contraception. 2015; 20(6):463-75. doi: 10.3109/13625187.2015.1068934. [PMID: 26212489]
  • Ingrid J M Duijkers, Christine Klipping, Yvette Zimmerman, Nicole Appels, Maud Jost, Catherine Maillard, Marie Mawet, Jean-Michel Foidart, Herjan J T Coelingh Bennink. Inhibition of ovulation by administration of estetrol in combination with drospirenone or levonorgestrel: Results of a phase II dose-finding pilot study. The European journal of contraception & reproductive health care : the official journal of the European Society of Contraception. 2015; 20(6):476-89. doi: 10.3109/13625187.2015.1074675. [PMID: 26394847]
  • N Pluchino, A N Santoro, E Casarosa, A Giannini, A Genazzani, M Russo, N Russo, P Petignat, A R Genazzani. Effect of estetrol administration on brain and serum allopregnanolone in intact and ovariectomized rats. The Journal of steroid biochemistry and molecular biology. 2014 Sep; 143(?):285-90. doi: 10.1016/j.jsbmb.2014.04.011. [PMID: 24787659]
  • Karine Chung, Linda J Hovanessian-Larsen, Debra Hawes, DeShawn Taylor, Susan Downey, Darcy V Spicer, Frank Z Stanczyk, Sherfaraz Patel, A Rebecca Anderson, Malcolm C Pike, Anna H Wu, Celeste Leigh Pearce. Breast epithelial cell proliferation is markedly increased with short-term high levels of endogenous estrogen secondary to controlled ovarian hyperstimulation. Breast cancer research and treatment. 2012 Apr; 132(2):653-60. doi: 10.1007/s10549-011-1870-y. [PMID: 22083231]
  • Paweł K Zarzycki, Elzbieta Włodarczyk, Michał J Baran. Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: II. Fast screening of free steroids and related low-molecular-mass compounds fraction in the environmental samples derived from surface waters, treated and untreated sewage waters as well as activated sludge material. Journal of chromatography. A. 2009 Oct; 1216(44):7612-22. doi: 10.1016/j.chroma.2009.03.066. [PMID: 19356767]
  • M Visser, C F Holinka, H J T Coelingh Bennink. First human exposure to exogenous single-dose oral estetrol in early postmenopausal women. Climacteric : the journal of the International Menopause Society. 2008; 11 Suppl 1(?):31-40. doi: 10.1080/13697130802056511. [PMID: 18464021]
  • H J T Coelingh Bennink, A-M Heegaard, M Visser, C F Holinka, C Christiansen. Oral bioavailability and bone-sparing effects of estetrol in an osteoporosis model. Climacteric : the journal of the International Menopause Society. 2008; 11 Suppl 1(?):2-14. doi: 10.1080/13697130701798692. [PMID: 18464016]
  • G L Hammond, K N Hogeveen, M Visser, H J T Coelingh Bennink. Estetrol does not bind sex hormone binding globulin or increase its production by human HepG2 cells. Climacteric : the journal of the International Menopause Society. 2008; 11 Suppl 1(?):41-6. doi: 10.1080/13697130701851814. [PMID: 18464022]
  • Paweł K Zarzycki, Kathrin M Kulhanek, Roger Smith, Vicki L Clifton. Determination of steroids in human plasma using temperature-dependent inclusion chromatography for metabolomic investigations. Journal of chromatography. A. 2006 Feb; 1104(1-2):203-8. doi: 10.1016/j.chroma.2005.11.119. [PMID: 16364333]
  • Yukiko Shimizu. [Estrogen: estrone (E1), estradiol (E2), estriol (E3) and estetrol (E4)]. Nihon rinsho. Japanese journal of clinical medicine. 2005 Aug; 63 Suppl 8(?):425-38. doi: . [PMID: 16149545]
  • Y Shimizu, T Yanaihara. [Estrogen: estrone (E1), estradiol (E2), estriol (E3) and estetrol (4)]. Nihon rinsho. Japanese journal of clinical medicine. 1999 Dec; 57 Suppl(?):252-65. doi: NULL. [PMID: 10778113]
  • J Noma, N Hayashi, K Sekiba. Automated direct high-performance liquid chromatographic assay for estetrol, estriol, cortisone and cortisol in serum and amniotic fluid. Journal of chromatography. 1991 Jul; 568(1):35-44. doi: 10.1016/0378-4347(91)80338-d. [PMID: 1770108]
  • S Takagi, H Sakamoto. [Clinical significance of estetrol analysis in endocrine tests of the gonadal and placental system]. Nihon rinsho. Japanese journal of clinical medicine. 1989 Dec; 48 Suppl(?):1257-9. doi: NULL. [PMID: 2533631]
  • T Kiriyama. [Study on the clinical evaluation of DHAS loading as a fetoplacental function test--effect of DHAS on estrogen metabolism at a fetoplacental unit]. Nihon Sanka Fujinka Gakkai zasshi. 1986 May; 38(5):700-8. doi: NULL. [PMID: 2941503]
  • M B Sampson, N Kundu, L P Peterson. Effect of the oxytocin challenge test on levels of maternal serum unconjugated serum estriol and estetrol pre- and post-test in high-risk pregnancies. American journal of perinatology. 1986 Jan; 3(1):22-3. doi: 10.1055/s-2007-999818. [PMID: 3942609]
  • V R Lupo, M Miodovnik, V S Hertzberg. Daily variation of serum unconjugated estriol and estetrol in normal pregnancy. American journal of perinatology. 1985 Oct; 2(4):330-7. doi: 10.1055/s-2007-999983. [PMID: 4052187]
  • N Hayashi, K Hayata, K Sekiba. Rapid and simultaneous measurement of estrone, estradiol, estriol and estetrol in serum by high performance liquid chromatography with electrochemical detection. Acta medica Okayama. 1985 Apr; 39(2):143-53. doi: 10.18926/amo/31517. [PMID: 4003113]
  • K Schollberg, E Seiler, S Wagner. Dehydroepiandrosterone sulphate loading test and determination of plasma oestetrol concentration in late pregnancy. Experimental and clinical endocrinology. 1985 Apr; 85(2):204-8. doi: 10.1055/s-0029-1210437. [PMID: 3160598]
  • K Tsukamoto. [The metabolism and conjugation of estrogens in the human fetus]. Nihon Naibunpi Gakkai zasshi. 1984 Sep; 60(9):1091-111. doi: 10.1507/endocrine1927.60.9_1091. [PMID: 6519315]
  • A Klopper. Diagnosis of growth retardation by biochemical methods. Clinics in obstetrics and gynaecology. 1984 Aug; 11(2):437-55. doi: 10.1016/s0306-3356(21)00518-5. [PMID: 6332704]
  • P J Meis, J E Buster, N Kundu, D Magyar, J R Marshall, F Halberg. Individualized cosinor assessment of circadian hormonal variation in third trimester human pregnancy. Chronobiologia. 1983 Jan; 10(1):1-11. doi: . [PMID: 6221911]
  • G Mitsukawa, M Hashino, J Suzuki, T Yanaihara, T Nakayama, H Mori. [Determination of serum unconjugated estetrol by selected ion monitoring with application of deuterated estetrol as an internal standard]. Nihon Sanka Fujinka Gakkai zasshi. 1982 Nov; 34(11):1859-66. doi: NULL. [PMID: 7175284]
  • T Kubota, Y Yaoi, A Suzuki, N Nishi, M Saito, T Kumasaka. [Effect of bromocriptine on the endocrine profile during pregnancy]. Nihon Sanka Fujinka Gakkai zasshi. 1982 Oct; 34(10):1675-83. doi: . [PMID: 7175275]
  • L Benassi, L Alfieri, D Debiasi, R Trentadue. Unconjugated estetrol in normal pregnancy. Clinical and experimental obstetrics & gynecology. 1982; 9(4):243-5. doi: NULL. [PMID: 7168899]
  • P V Grella, M Enrichi, G Tambuscio, O Ronsisvalle, G Murari, P Resta, G B Nardelli, F Sormani-Zodo, G Barazzuol, D Marchesoni. What are the most suitable fetoplacental tests in the monitoring of the third trimester of pregnancy?. Clinical and experimental obstetrics & gynecology. 1982; 9(2):69-73. doi: NULL. [PMID: 6186418]
  • N Kundu, M Wachs, G B Iverson, L P Petersen. Comparison of serum unconjugated estriol and estetrol in normal and complicated pregnancies. Obstetrics and gynecology. 1981 Sep; 58(3):276-81. doi: NULL. [PMID: 7266946]
  • M Izumi. [Amniotic fluid cortisol, tetrahydrocortisone, estriol and estetrol in normal and high risk pregnancy (author's transl)]. Nihon Sanka Fujinka Gakkai zasshi. 1981 Aug; 33(8):1245-54. doi: . [PMID: 7276651]
  • K Muraguchi, K Takahashi, M Suzuki, N Ikeno. [The concentration of serum unconjugated estradiol, estriol and estetrol in pregnant women, and the significance of these hormones in pregnancy (author's transl)]. Nihon Naibunpi Gakkai zasshi. 1981 Jul; 57(7):974-82. doi: 10.1507/endocrine1927.57.7_974. [PMID: 7286352]
  • Y Sagara, Y Okatani, Y Takeda, A Kambegawa. [The determination of unconjugated estrone, estradiol, estriol and estetrol in serum or amniotic fluid by high performance liquid chromatography with an amperometric detector (author's transl)]. Nihon Naibunpi Gakkai zasshi. 1981 Jul; 57(7):963-73. doi: 10.1507/endocrine1927.57.7_963. [PMID: 7286351]
  • K Schollberg, E Seiler, S Wagner. [Estetrol determination in the serum after i.v. application of dehydroepiandrosterone sulfate in late pregnancy]. Acta Universitatis Palackianae Olomucensis Facultatis Medicae. 1981; 101(?):22-7. doi: NULL. [PMID: 6211049]
  • K Schollberg, E Seiler, S Wagner. [Serum estetrol levels following i.v.administration of dehydroepiandrosterone sulfate in late pregnancy]. Acta Universitatis Palackianae Olomucensis Facultatis Medicae. 1981; 101(?):22-7. doi: NULL. [PMID: 6242690]
  • K Muraguchi. [Concentration of serum unconjugated estriol and estetrol in pregnant women with intrauterine growth retardation, and significance of these hormones in pregnancy (author's transl)]. Nihon Sanka Fujinka Gakkai zasshi. 1981 Jan; 33(1):41-50. doi: . [PMID: 7229455]
  • L Gualandi, L Modelli, G Maurizio, M Filicori, G Bolelli. Plasma levels of unconjugated estetrol and estriol and of total estriol in normal human pregnancy. Acta Europaea fertilitatis. 1979 Jun; 10(2):77-87. doi: . [PMID: 545977]
  • L De Cecco, G L Capitanio, P Lanera, E Pedretti, N Ragni, P Rossato, P L Venturini. Estradiol and estetrol plasma levels before and after intravenous administration of dehydroepiandrosterone sulfate in normal and pathologic pregnancies. Acta Europaea fertilitatis. 1979 Mar; 10(1):1-13. doi: . [PMID: 161846]
  • G C Zucchelli, D Giannessi, M A Piro, M Ferdeghini, R Malvano. Radioimmunoassay of unconjugated and total serum estetrol using a 125I-iodinated tracer. Hormone research. 1979; 11(5):227-39. doi: 10.1159/000179059. [PMID: 574850]
  • S Bélisle. [Hormonal dynamics during pregnancy: critical discussion and clinical interpretations]. Canadian Medical Association journal. 1978 Dec; 119(11):1307-9. doi: NULL. [PMID: 153779]
  • O Axelsson. Unconjugated oestetrol in plasma in response to an intravenous load of dehydroepiandrosterone sulphate (DHAS) in uncomplicated and complicated human pregnancy. Acta endocrinologica. 1978 Dec; 89(4):753-62. doi: 10.1530/acta.0.0890753. [PMID: 152556]
  • N Kundu, P J Carmody, S M Didolkar, L P Petersen. Sequential determination of serum human placental lactogen, estriol, and estetrol for assessment of fetal morbidity. Obstetrics and gynecology. 1978 Nov; 52(5):513-20. doi: . [PMID: 724167]
  • J Presl. [Estetrol and the prediction of threatened fetus]. Ceskoslovenska gynekologie. 1978 Apr; 43(3):201-2. doi: NULL. [PMID: 647803]
  • H A Schut, J M Bowman, S Solomon. Precursor role of 15alpha-hydroxyestradiol and 15alpha-hydroxyandrostenedione in the formation of estetrol. Canadian journal of biochemistry. 1978 Feb; 56(2):101-6. doi: 10.1139/o78-016. [PMID: 630454]
  • K Den, H Matsumoto, K Fujii, K Furuya, T Yoshida, S Takagi, A Kanbegawa, T Kokubu. A radioimmunoassay of plasma unconjugated and conjugated estetrol. Steroids. 1977 Oct; 30(4):521-9. doi: 10.1016/0039-128x(77)90097-6. [PMID: 204082]
  • S Belisle, R Osathanondh, D Tulchinsky. The effect of constant infusion of unlabeled dehydroepiandrosterone sulfate on maternal plasma androgens and estrogens. The Journal of clinical endocrinology and metabolism. 1977 Sep; 45(3):544-50. doi: 10.1210/jcem-45-3-544. [PMID: 143476]
  • R M Boyar, C Nogeire, D Fukushima, L Hellman, J Fishman. Studies of the diurnal pattern of plasma corticosteroids and gonadotropins in two cases of feminizing adrenal carcinoma: measurements of estrogen and corticosteroid production. The Journal of clinical endocrinology and metabolism. 1977 Jan; 44(1):39-45. doi: 10.1210/jcem-44-1-39. [PMID: 137914]
  • N Kundu, M Grant. Radioimmunoassay of 15alpha-hydroxyestriol (estetrol) in pregnancy serum. Steroids. 1976 Jun; 27(6):785-96. doi: 10.1016/0039-128x(76)90138-0. [PMID: 941193]
  • J S Elce, P P Lai. Water-soluble metabolites of the estrogens. Quantitation of C-18 tetrols in rat feces. Steroids. 1976 Mar; 27(3):335-52. doi: 10.1016/0039-128x(76)90055-6. [PMID: 178075]
  • A R Korda, J J Challis, A B Anderson, A C Turnbull. Plasma unconjugated 15alpha-hydroxyoestriol (oestetrol) levels in normal human pregnancy. British journal of obstetrics and gynaecology. 1975 Nov; 82(11):882-6. doi: 10.1111/j.1471-0528.1975.tb00592.x. [PMID: 1191602]
  • P A Weiss, H E Esterbauer, F Scherr. [Excretion of estriol, estetrol, 16-epi-estriol, 16-keto-estradiol and 16-hydroxyestrone in the 24-hour urine of pregnant women in the last trimester]. Endokrinologie. 1975 Aug; 65(3):254-65. doi: . [PMID: 1222727]
  • D Tulchinsky, F D Frigoletto, K J Ryan, J Fishman. Plasma estetrol as an index of fetal well-being. The Journal of clinical endocrinology and metabolism. 1975 Apr; 40(4):560-7. doi: 10.1210/jcem-40-4-560. [PMID: 805156]
  • A E Schindler, H Sparke. Steroids in umbilical cord plasma from normal term deliveries. Endokrinologie. 1975 Feb; 65(1):80-90. doi: NULL. [PMID: 126148]