Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 05:16:42 UTC |
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Update Date | 2014-12-24 20:26:57 UTC |
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Accession Number | T3D4790 |
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Identification |
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Common Name | Estriol |
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Class | Small Molecule |
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Description | A hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. It is however available in the United States by prescription filled only by compounding pharmacies. It has also been approved and marketed throughout Europe and Asia for approximately 40 years for the treatment of post-menopausal hot flashes. |
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Compound Type | - Animal Toxin
- Drug
- Food Toxin
- Metabolite
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | Synonym | (16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol | (16α,17β)-estra-1,3,5(10)-triene-3,16,17-triol | 1,3,5(10)-Estratriene-3,16-alpha,17beta-triol | 13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triol | 16-alpha,17-beta-Estriol | 16-alpha,17-beta-Oestriol | 16-alpha-Hydroxyestradiol | 16a,17b-Estriol | 16a-Estriol | 16a-Hydroxyestradiol | 16alpha,17beta-Estriol | 16alpha,17beta-Oestriol | 16alpha-Hydroxy-17beta-estradiol | 16alpha-Hydroxyestradiol | 16alpha-Hydroxyoestradiol | 16α-hydroxyestradiol | 3,16a,17b-Estriol | 3,16a,17b-Trihydroxyestra-1,3,5(10)-triene | 3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene | 3,16alpha,17beta-Trihydroxy-delta(1,3,5)-estratriene | 3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-triene | Aacifemine | Colpoestriol | Colpogyn | Colpovister | Destriol | Deuslon A | Deuslon-A | Estra-1,3,5(10)-triene-3,16a,17b-triol | Estratriol | Estriel | Follicular hormone hydrate | Gynasan | Hemostyptanon | Holin V | Hormomed | Incurin | Klimax E | Klimoral | Oekolp | Oestratriol | Oestriol | Oestriolum | Orestin | Orgastyptin | Ortho-Gynest | Ovesterin | Ovestin | Ovestinon | Ovestrion | Ovo-Vinces | Synapause E | Theelol | Tridestrin | Trihydroxyestrin | Triovex |
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Chemical Formula | C18H24O3 |
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Average Molecular Mass | 288.381 g/mol |
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Monoisotopic Mass | 288.173 g/mol |
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CAS Registry Number | 50-27-1 |
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IUPAC Name | (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol |
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Traditional Name | (1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol |
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SMILES | [H][C@@]1(O)C[C@@]2([H])[C@]3([H])CCC4=CC(O)=CC=C4[C@@]3([H])CC[C@]2(C)[C@@]1([H])O |
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InChI Identifier | InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1 |
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InChI Key | InChIKey=PROQIPRRNZUXQM-ZXXIGWHRSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Estrane steroids |
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Direct Parent | Estrogens and derivatives |
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Alternative Parents | |
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Substituents | - Estrogen-skeleton
- 3-hydroxysteroid
- 17-hydroxysteroid
- 16-hydroxysteroid
- 16-alpha-hydroxysteroid
- Hydroxysteroid
- Phenanthrene
- Tetralin
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- 1,2-diol
- Polyol
- Organooxygen compound
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | - Adrenal Cortex
- Adrenal Gland
- Kidney
- Liver
- Placenta
- Testes
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 82-86°C | Boiling Point | Not Available | Solubility | Not Available | LogP | 2.45 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-005a-1983000000-2f46d0d29b48132f7670 | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-4970000000-1aa2bbf3f32fd687c37d | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-005a-1983000000-2f46d0d29b48132f7670 | 2017-09-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ab9-1390000000-492aa66975c4e026b9d8 | 2017-08-28 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-009i-2033900000-46c301a46b654b6c6bf3 | 2017-10-06 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-5900000000-2102cb581ac98fea87b0 | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-1900000000-1fab12be883127f80c67 | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4i-5900000000-2102cb581ac98fea87b0 | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive | splash10-000i-4970000000-1aa2bbf3f32fd687c37d | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-000i-0390000000-891430228022fb330b42 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-7ce66600861479086f4f | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-000i-1970000000-6d5c77ab4f1744109b86 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-331480c31f6585f70cf2 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0zg0-0590000000-6ee9bd7dbdbd777f46a4 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-2900000000-d7ae7d481cc02d1ab839 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-2920000000-d7d95b3d24e7be97e848 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-3aa436f48e23664bd455 | 2021-09-20 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0190000000-b047d204e97271aa8a65 | 2017-07-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dr-0490000000-c0c0bd8b1dc1381c06fa | 2017-07-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ufr-3950000000-b7180dbe548021fd7fc9 | 2017-07-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-743915792d6f69593b2b | 2017-07-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-8469d578b4631e8de995 | 2017-07-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02p0-0190000000-738399876b56d0e183d5 | 2017-07-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-843a74fabb1d0eb512a1 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00kr-0090000000-4e0854fb8be9cf34de97 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02br-0090000000-70686fa9219ae093945a | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-1126a56061a8c854c755 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fga-0790000000-a1dba0b6195890b30d91 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6v-3910000000-64d9abb8f215c1264e1f | 2021-09-22 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-000i-3950000000-c2f0781bc5056d66aaf5 | 2014-09-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental) | Not Available | 2012-12-04 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | Not Available | 2012-12-04 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Estriol levels can be measured to give an indication of the general health of the fetus. DHEA-S is produced by the adrenal cortex of the fetus. This is converted to estriol by the placenta. If levels of "unconjugated estriol" are abnormally low in a pregnant woman, this may indicate a problem with the development of the child. The drug interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estriol upon the target cell. 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. |
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Metabolism | Not Available |
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Toxicity Values | ORAL (LD50): Acute: >2000 mg/kg [Rat]. |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Used as a test to determine the general health of an unborn fetus. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB04573 |
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HMDB ID | HMDB00153 |
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PubChem Compound ID | 5756 |
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ChEMBL ID | CHEMBL193482 |
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ChemSpider ID | 5553 |
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KEGG ID | C05141 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 27974 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | ESL |
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ACToR ID | Not Available |
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Wikipedia Link | Estriol |
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References |
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Synthesis Reference | James V. Freeman, Gary M. Johnson, “Synthesis of 6.alpha.-functionalized estriol haptens and protein conjugates thereof.” U.S. Patent US5902888, issued June, 1973. |
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MSDS | Link |
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General References | - Soldan SS, Alvarez Retuerto AI, Sicotte NL, Voskuhl RR: Immune modulation in multiple sclerosis patients treated with the pregnancy hormone estriol. J Immunol. 2003 Dec 1;171(11):6267-74. [14634144 ]
- Diczfalusy E: The early history of estriol. J Steroid Biochem. 1984 Apr;20(4B):945-53. [6374294 ]
- Kashork CD, Sutton VR, Fonda Allen JS, Schmidt DE, Likhite ML, Potocki L, O'Brien WE, Shaffer LG: Low or absent unconjugated estriol in pregnancy: an indicator for steroid sulfatase deficiency detectable by fluorescence in situ hybridization and biochemical analysis. Prenat Diagn. 2002 Nov;22(11):1028-32. [12424769 ]
- Furuhashi N, Tsujiei M: [Clinical significance of serum and urinary estriol analysis in endocrine tests of the gonadal and placental system]. Nihon Rinsho. 1989 Dec;48 Suppl:1260-2. [2621854 ]
- Ronin-Walknowska E, Szczygielski A, Skoczowska M: [Usefulness of determining free estriol, placental lactogen, progesterone, placental alkaline phosphatase, uric acid, hematocrit, hemoglobin and proteins in the blood and estrogen in the urine in the prognosis of the status of newborn infants in EPH gestosis]. Ginekol Pol. 1987 Jan;58(1):21-6. [3583036 ]
- Fredricsson B, Carlstrom K, Eneroth P: Short-term variations in urinary estriol and renal function. Possible effects of extraneous conditions. Gynecol Obstet Invest. 1978;9(5):268-76. [752645 ]
- Andreolini F, Borra C, Caccamo F, Di Corcia A, Nicoletti I, Samperi R, Improta F: Estriol and its conjugates in late pregnancy determined by extraction with Carbopack B and liquid chromatography with fluorometric detection. Clin Chem. 1985 Oct;31(10):1698-702. [2994907 ]
- Truran PL, Read GF, Walker S: Radioimmunoassay for salivary estriol, with use of an 125I radioligand and a solid-phase separation technique. Clin Chem. 1982 Dec;28(12):2393-7. [7139918 ]
- Izumi H, Saito N, Ichiki S, Makino Y, Yukitake K, Kaneoka T: Prenatal diagnosis of congenital lipoid adrenal hyperplasia. Obstet Gynecol. 1993 May;81(5 ( Pt 2)):839-41. [8469492 ]
- Guedeney X, Chanez C, Grenier A, Scherrmann JM: Temperature-dependent immunoreactive assay to screen for digoxin-like immunoreactive factor(s). Clin Chem. 1991 Nov;37(11):1900-4. [1718632 ]
- Andreolini F, Di Corcia A, Lagana A, Samperi R, Raponi G: Preliminary isolation of urinary placental estriol before gas or liquid chromatography. Clin Chem. 1983 Dec;29(12):2076-8. [6640903 ]
- Evans JJ, Wilkinson AR, Aickin DR: Salivary estriol concentrations during normal pregnancies, and a comparison with plasma estriol. Clin Chem. 1984 Jan;30(1):120-1. [6690116 ]
- Kono H, Furuhashi N, Shinkawa O, Takahashi T, Tsujiei M, Yajima A: The maternal serum cortisol levels after onset of labor. Tohoku J Exp Med. 1987 Jun;152(2):133-7. [3629582 ]
- Moore ML: Biochemical markers for preterm labor and birth: what is their role in the care of pregnant women? MCN Am J Matern Child Nurs. 1999 Mar-Apr;24(2):80-6. [10083784 ]
- Pentikainen PJ, Pentikainen LA, Azarnoff DL, Dujovne CA: Plasma levels and excretion of estrogens in urine in chronic lever disease. Gastroenterology. 1975 Jul;69(1):20-7. [1171044 ]
- Nutman A, Freud E, Itzhaky D, Dolfin T, Tepper R: High maternal estriol level in pregnancy as a predictor of surgical intervention for undescended testis. Fertil Steril. 2005 Jul;84(1):249-52. [16009196 ]
- Pasqualini JR: Enzymes involved in the formation and transformation of steroid hormones in the fetal and placental compartments. J Steroid Biochem Mol Biol. 2005 Dec;97(5):401-15. Epub 2005 Oct 3. [16202579 ]
- Lardy H, Marwah A, Marwah P: C(19)-5-ene steroids in nature. Vitam Horm. 2005;71:263-99. [16112271 ]
- Shinawi M, Szabo S, Popek E, Wassif CA, Porter FD, Potocki L: Recognition of Smith-Lemli-Opitz syndrome (RSH) in the fetus: utility of ultrasonography and biochemical analysis in pregnancies with low maternal serum estriol. Am J Med Genet A. 2005 Sep 15;138(1):56-60. [16097001 ]
- Trimesta [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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