<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2014-09-11 05:13:46 UTC</creation_date>
  <update_date>2026-08-22 04:03:52 UTC</update_date>
  <accession>T3D4730</accession>
  <common_name>Medroxyprogesterone Acetate</common_name>
  <class>SmallMolecule</class>
  <description>Medroxyprogesterone Acetate (C24H34O4) is an exogenous compound with an average molecular weight of 386.52 g/mol. It exists as a solid at room temperature. Medroxyprogesterone Acetate belongs to the pregnane steroids, a subclass of steroids and steroid derivatives within the organic compounds. This compound is classified under the superclass of lipids and lipid-like molecules.

The compound interacts with two recorded protein targets: the progesterone receptor (PGR) and the estrogen receptor (ESR1). Medroxyprogesterone Acetate has been identified in or released from 57 recorded sources. These include electrical and electronic equipment such as antennas, amplifiers, coils, auxiliary devices, and adjustable resistors. Within household cleaning and consumer products, it is found in bleaching agents, perfumes within detergents and soaps, cigar cigarettes, ash trays, and non electric simulated smoking devices. In building and construction, it is associated with roofs, floors, ceilings, fencing, and ladders. It is also found in household items such as watch chains and rosaries. Additionally, the compound is present in food, food processing, and cookware, specifically in food preservation, fermentation processes for beer, the preparation of malt, the preparation of wort, and the preparation of wine or sparkling wine.</description>
  <categories>
    <category>Drug</category>
    <category>Synthetic Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Ether</type>
    <type>Ester</type>
    <type>Drug</type>
    <type>Antineoplastic Agent, Hormonal</type>
    <type>Synthetic Compound</type>
    <type>Contraceptive Agent</type>
    <type>Contraceptive Agent, Female</type>
    <type>Contraceptive Agent, Male</type>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>(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</synonym>
    <synonym>(6alpha)-17-(Acetyloxy)-6-methylpreg-4-ene-3,20-dione</synonym>
    <synonym>17-Acetoxy-6alpha-methylprogesterone</synonym>
    <synonym>17-Acetoxy-6α-methylprogesterone</synonym>
    <synonym>17alpha-Hydroxy-6alpha-methylprogesterone acetate</synonym>
    <synonym>17α-hydroxy-6α-methylprogesterone acetate</synonym>
    <synonym>6-alpha-Methyl-17-alpha-acetoxyprogesterone</synonym>
    <synonym>6-alpha-Methyl-17-alpha-hydroxyprogesterone acetate</synonym>
    <synonym>6alpha-Methyl-17-acetoxy progesterone</synonym>
    <synonym>6alpha-Methyl-17alpha-hydroxyprogesterone acetate</synonym>
    <synonym>6alpha-Methyl-4-pregnene-3,20-dion-17alpha-ol acetate</synonym>
    <synonym>6α-Methyl-17-acetoxy progesterone</synonym>
    <synonym>6α-Methyl-17α-hydroxyprogesterone acetate</synonym>
    <synonym>Depo-provera</synonym>
    <synonym>Depo-subq provera 104</synonym>
    <synonym>Makena</synonym>
    <synonym>Medroxyacetate progesterone</synonym>
    <synonym>Medroxyprogesterone 17-acetate</synonym>
    <synonym>Medroxyprogesterone acetate</synonym>
    <synonym>Medroxyprogesterone acetic acid</synonym>
    <synonym>Methylacetoxyprogesterone</synonym>
    <synonym>Metigestrona</synonym>
    <synonym>MPA</synonym>
    <synonym>Provera</synonym>
  </synonyms>
  <chemical_formula>C24H34O4</chemical_formula>
  <average_molecular_weight>386.5244</average_molecular_weight>
  <monisotopic_moleculate_weight>386.245709576</monisotopic_moleculate_weight>
  <iupac_name>(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_name>
  <traditional_iupac>provera</traditional_iupac>
  <cas_registry_number>71-58-9</cas_registry_number>
  <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</smiles>
  <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</inchi>
  <inchikey>PSGAAPLEWMOORI-PEINSRQWSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Alpha-acyloxy ketones</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Steroid esters</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-acyloxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Steroid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>steroid ester</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Membrane</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Medroxyprogesterone acetate Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143051</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>214.5°C</value>
    </property>
    <property>
      <kind>solubility</kind>
      <value>22.2mg/L</value>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.5</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.21e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>386.5244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>386.245709576</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H34O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PSGAAPLEWMOORI-PEINSRQWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>107.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>44.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure>Rapidly absorbed from GI tract</route_of_exposure>
  <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.&#13;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.&#13;Half Life: 50 days</metabolism>
  <toxicity/>
  <lethaldose/>
  <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/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bf86285c8&gt;</health_effects>
  <symptoms>Side effects include loss of bone mineral density, BMD changes in adult women, bleeding irregularities, cancer risks, and thromboembolic disorders.</symptoms>
  <treatment/>
  <drugbank_id>DB00603</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>6279</pubchem_compound_id>
  <chembl_id>CHEMBL717</chembl_id>
  <chemspider_id>6043</chemspider_id>
  <kegg_id>C08150</kegg_id>
  <uniprot_id/>
  <omim_id/>
  <chebi_id>6715</chebi_id>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia>Medroxyprogesterone</wikipidia>
  <general_references>
    <reference>
      <pubmed_id>19434889</pubmed_id>
    </reference>
    <reference>
      <pubmed_id>1119869</pubmed_id>
    </reference>
    <reference>
      <reference_text>International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php</reference_text>
    </reference>
  </general_references>
  <targets>
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</compound>
