Medroxyprogesterone (CHEM003659)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (19)XML
Record Information
Version1.0
Creation Date2014-09-11 02:05:35 UTC
Update Date2026-04-13 20:33:53 UTC
Accession NumberCHEM003659
Identification
Common NameMedroxyprogesterone
ClassSmall Molecule
DescriptionMedroxyprogesterone is a synthetic progesterone (steroid hormone) involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen. Progesterone's reproductive function serves to convert the endometrium to its secretory stage to prepare the uterus for implantation. If pregnancy does not occur, progesterone levels will decrease leading to menstruation in the human. Normal menstrual bleeding is a progesterone withdrawal bleeding. During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine musculature. The fetus metabolizes placental progesterone in the production of adrenal mineralo and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production. Progesterone has an effect upon vaginal epithelium and cervical mucus. A synthetic progestational hormone used in veterinary practice as an estrus regulator.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Drug
  • Ester
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
17-Hydroxy-6alpha-methyl-pregn-4-ene-3,20-dioneChEBI
17-Hydroxy-6alpha-methylprogesteroneChEBI
17alpha-Hydroxy-6alpha-methylprogesteroneChEBI
6alpha-Methyl-17alpha-hydroxyprogesteroneChEBI
6alpha-Methyl-4-pregnen-17alpha-ol-3,20-dioneChEBI
MedroxiprogesteronaChEBI
MedroxyprogesteronChEBI
MedroxyprogesteronumChEBI
Farlutal inyectableKegg
17-Hydroxy-6a-methyl-pregn-4-ene-3,20-dioneGenerator
17-Hydroxy-6α-methyl-pregn-4-ene-3,20-dioneGenerator
17-Hydroxy-6a-methylprogesteroneGenerator
17-Hydroxy-6α-methylprogesteroneGenerator
17a-Hydroxy-6a-methylprogesteroneGenerator
17Α-hydroxy-6α-methylprogesteroneGenerator
6a-Methyl-17a-hydroxyprogesteroneGenerator
6Α-methyl-17α-hydroxyprogesteroneGenerator
6a-Methyl-4-pregnen-17a-ol-3,20-dioneGenerator
6Α-methyl-4-pregnen-17α-ol-3,20-dioneGenerator
CycrinHMDB
Depo-proveraHMDB
Depo-subq provera 104HMDB
FarlutalHMDB
MedrossiprogesteroneHMDB
MedroxiprogesteronumHMDB
Medroxyprogesterone acetateHMDB
ProveraHMDB
17 alpha Hydroxy 6 alpha methylprogesteroneHMDB
Medroxyprogesterone strakan brandHMDB
Strakan brand OF medroxyprogesteroneHMDB
17 alpha-Hydroxy-6 alpha-methylprogesteroneHMDB
Adgyn medroHMDB
MethylhydroxyprogesteroneHMDB
Chemical FormulaC22H32O3
Average Molecular Mass344.488 g/mol
Monoisotopic Mass344.235 g/mol
CAS Registry Number520-85-4
IUPAC Name(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
SMILES[H][C@@]12CC[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
InChI IdentifierInChI=1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1
InChI KeyFRQMUZJSZHZSGN-HBNHAYAOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point214.5 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.52ALOGPS
logP3.69ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.7ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.65 m³·mol⁻¹ChemAxon
Polarizability40.07 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00tf-4297000000-cd7180f050ed3c53c6efSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uki-2297500000-c6975631306bc23561a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-1339000000-b79365e841d4bec0f180Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00dj-3910000000-9983023f32301e1fba4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-00dj-8900000000-79ac294ddbd774821e12Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0319000000-a0d745584bc883eda4a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0319000000-a0d745584bc883eda4a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-4931000000-13a32e65d38099780615Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0219000000-053fe09f5f581304e489Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0931000000-cf29ab5c482da194c793Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-dce8dfd249bbc8536b02Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-006t-2926000000-27ffccce12006e18344aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0910000000-b3401643e191b15ec5c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00di-0900000000-e3c170bb53acd6540911Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-006t-3907000000-e2ef8aee0b8ef98652d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0097000000-9c484cc7f2b792d00c25Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0019000000-435bcb637366453b98bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0209000000-8f976444cc5262c1c92cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00di-0900000000-0b0c65efe5b7c9520650Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0096000000-c57e97b64656d5c2454bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0002-0090000000-e6ace08882d55359ec8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-860975266cd1b971e6abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fvj-0189000000-ec97befb496198e1f69fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1691000000-2eabdaeb463f59c27177Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-eabfc17143af207764c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-0029000000-3cbdd488660baed87ee9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00g0-0094000000-1cee9f40fb0d5cf31715Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001939
FooDB IDFDB022754
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1094
PDB IDNot Available
Wikipedia LinkMedroxyprogesterone
Chemspider ID10185
ChEBI ID6715
PubChem Compound ID10631
Kegg Compound IDC07119
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18636214
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=31902997