<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3105</id>
  <title>T3D3063</title>
  <common-name>Quinestrol</common-name>
  <description>Quinestrol is only found in individuals that have used or taken this drug. It is a 3-cyclopentyl ether of ethinyl estradiol. Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen 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 estradiol 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. 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).</description>
  <cas>152-43-2</cas>
  <pubchem-id>9046</pubchem-id>
  <chemical-formula>C25H32O2</chemical-formula>
  <weight>364.240230</weight>
  <appearance>White powder.</appearance>
  <melting-point>107.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1.57e-03 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Absorbed following oral administration.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen 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 estradiol 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. 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).</mechanism-of-toxicity>
  <metabolism>Metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is metabolized in the liver. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Used in hormone replacement therapy, treating symptoms of menopause such as hot flashes. Also used to treat breast and prostate cancer.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Side effects include liver and kidney dysfunction, high blood pressure, heart disease, degeneration of the testicles, premature baldness, and acne.</health-effects>
  <symptoms>Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:58Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:56Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Quinestrol</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07619</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>8716</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Quinestrol</stitch-id>
  <drugbank-id>DB04575</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC4CCCC4)C=C3CC[C@@]21[H]</moldb-smiles>
  <moldb-formula>C25H32O2</moldb-formula>
  <moldb-inchi>InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=PWZUUYSISTUNDW-VAFBSOEGSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">364.5204</moldb-average-mass>
  <moldb-mono-mass type="decimal">364.240230268</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB15579</hmdb-id>
  <chembl-id>CHEMBL1201165</chembl-id>
  <chemspider-id>8694</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
