<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4785</id>
  <title>T3D4730</title>
  <common-name>Medroxyprogesterone Acetate</common-name>
  <description>Medroxyprogesterone acetate (INN, USAN, BAN), also known as 17‘±-hydroxy-6‘±-methylprogesterone acetate, and commonly abbreviated as MPA, is a steroidal progestin, a synthetic variant of the human hormone progesterone. It is used as a contraceptive, in hormone replacement therapy and for the treatment of endometriosis as well as several other indications. MPA is a more potent derivative of its parent compound medroxyprogesterone (MP). While medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate, what is normally being administered is MPA and not MP. </description>
  <cas>71-58-9</cas>
  <pubchem-id>6279</pubchem-id>
  <chemical-formula>C24H34O4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>214.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>22.2mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Rapidly absorbed from GI tract</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Progestins diffuse freely into target cells in the female reproductive tract, mammary gland, hypothalamus, and the pituitary and bind to the progesterone receptor. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH surge.</mechanism-of-toxicity>
  <metabolism>Hepatic.Route of Elimination: Following oral dosing, MPA is extensively metabolized in the liver via hydroxylation, with subsequent conjugation and elimination in the urine. Most MPA metabolites are excreted in the urine as glucuronide conjugates with only minor amounts excreted as sulfates.Half Life: 50 days</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>Used as a contraceptive and to treat secondary amenorrhea, abnormal uterine bleeding, pain associated with endometriosis, endometrial and renal cell carcinomas, paraphilia in males, GnRH-dependent forms of precocious puberty, as well as to prevent endometrial changes associated with estrogens.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Side effects include loss of bone mineral density, BMD changes in adult women, bleeding irregularities, cancer risks, and thromboembolic disorders.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:13:46Z</created-at>
  <updated-at type="dateTime">2026-03-27T00:47:19Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Medroxyprogesterone</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C08150</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>6715</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00603</drugbank-id>
  <pdb-id nil="true"/>
  <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@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)CC[C@]12C</moldb-smiles>
  <moldb-formula>C24H34O4</moldb-formula>
  <moldb-inchi>InChI=1S/C24H34O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13-14,18-20H,6-12H2,1-5H3/t14-,18+,19-,20-,22+,23-,24-/m0/s1</moldb-inchi>
  <moldb-inchikey>PSGAAPLEWMOORI-PEINSRQWSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">386.5244</moldb-average-mass>
  <moldb-mono-mass type="decimal">386.245709576</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.5</logp>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL717</chembl-id>
  <chemspider-id>6043</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;Klaus &lt;span class="caps"&gt;ANNEN&lt;/span&gt;, Thomas Linz, Karl-Heinz Neff, Rolf Bohlmann, Henry Laurent, &amp;#8220;&lt;span class="caps"&gt;PROCESS&lt;/span&gt; &lt;span class="caps"&gt;FOR&lt;/span&gt; &lt;span class="caps"&gt;PREPARING&lt;/span&gt; 17ALPHA-&lt;span class="caps"&gt;ACETOXY&lt;/span&gt;-6-&lt;span class="caps"&gt;METHYLENEPREGN&lt;/span&gt;-4-&lt;span class="caps"&gt;ENE&lt;/span&gt;-3,20-&lt;span class="caps"&gt;DIONE&lt;/span&gt;, &lt;span class="caps"&gt;MEDROXYPROGESTERONE&lt;/span&gt; &lt;span class="caps"&gt;ACETATE&lt;/span&gt; &lt;span class="caps"&gt;AND&lt;/span&gt; &lt;span class="caps"&gt;MEGESTROL&lt;/span&gt; &lt;span class="caps"&gt;ACETATE&lt;/span&gt;.&amp;#8221; U.S. Patent US20090012321, issued January 08, 2009.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003687</chemdb-id>
  <dsstox-id>DTXSID0025527</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00006415</susdat-id>
  <iupac>(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate</iupac>
</compound>
