<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3052</id>
  <title>T3D3010</title>
  <common-name>Fluoxymesterone</common-name>
  <description>Fluoxymesterone is only found in individuals that have used or taken this drug. It is an anabolic steroid that has been used in the treatment of male hypogonadism, delayed puberty in males, and in the treatment of breast neoplasms in women. [PubChem] Fluoxymesterone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, fluoxymesterone binds to the androgen receptor. It produces retention of nitrogen, sodium, potassium, and phosphorus; increases protein anabolism; decreases amino acid catabolism and decreased urinary excretion of calcium. The antitumour activity of fluoxymesterone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.</description>
  <cas>76-43-7</cas>
  <pubchem-id>6446</pubchem-id>
  <chemical-formula>C20H29FO3</chemical-formula>
  <weight>336.210070</weight>
  <appearance>White powder.</appearance>
  <melting-point>265°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>67.5 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral absorption is less than 44%.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Fluoxymesterone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, fluoxymesterone binds to the androgen receptor. It produces retention of nitrogen, sodium, potassium, and phosphorus; increases protein anabolism; decreases amino acid catabolism and decreased urinary excretion of calcium. The antitumour activity of fluoxymesterone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.</mechanism-of-toxicity>
  <metabolism>Presence of 17-alpha alkyl group reduces susceptibility to hepatic enzyme degradation, which slows metabolism and allows oral administration. Inactivation of testosterone occurs primarily in the liver
Half Life: 9.2 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>In males, used as replacement therapy in conditions associated with symptoms of deficiency or absence of endogenous testosterone. In females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:34Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:55Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Fluoxymesterone</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>5120</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Fluoxymesterone</stitch-id>
  <drugbank-id>DB01185</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@](C)(O)[C@@]1(C)C[C@]([H])(O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C</moldb-smiles>
  <moldb-formula>C20H29FO3</moldb-formula>
  <moldb-inchi>InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=YLRFCQOZQXIBAB-RBZZARIASA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">336.4409</moldb-average-mass>
  <moldb-mono-mass type="decimal">336.210072999</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.38</logp>
  <hmdb-id>HMDB15316</hmdb-id>
  <chembl-id>CHEMBL1445</chembl-id>
  <chemspider-id>6205</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>&lt;p&gt;U.S. Patent 2,793,218&lt;br /&gt;
U.S. Patent 2,813,881&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
