DIENOGEST (CED0006337)

Record Information
Version1.0
Creation Date2016-06-03 11:27:02 UTC
Update Date2026-08-20 06:15:10 UTC
Accession NumberCHEM043928
Identification
Common NameDIENOGEST
ClassSmall Molecule
Description
Dienogest is an organic compound with the chemical formula C20H25NO2 and an average molecular weight of 311.43 g/mol. DIENOGEST belongs to the oxosteroids, a subclass of steroids and steroid derivatives within the organic compounds. This compound is recorded as being found in or released from five sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is used in progestogens, progestogens and estrogens in combination, and hormonal contraceptives for systemic use. It is also associated with household cleaning and consumer products, specifically non electric simulated smoking devices and cigar cigarettes. The recorded route of exposure for dienogest is oral. Regarding its biological activity, two protein targets have been recorded: it acts as an agonist/antagonist of the androgen receptor (AR) and the progesterone receptor (PGR).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(17-Hydroxy-3-oxoestra-4,9-dien-17beta-yl)acetonitrileChEBI
17alpha-Cyanomethyl-17beta-hydroxyestra-4,9(10)-dien-3-oneChEBI
DienogestumChEBI
EndometrionKegg
(17-Hydroxy-3-oxoestra-4,9-dien-17b-yl)acetonitrileGenerator
(17-Hydroxy-3-oxoestra-4,9-dien-17β-yl)acetonitrileGenerator
17a-Cyanomethyl-17b-hydroxyestra-4,9(10)-dien-3-oneGenerator
17Α-cyanomethyl-17β-hydroxyestra-4,9(10)-dien-3-oneGenerator
STS-557MeSH
17 alpha-Cyanomethyl-17 beta-hydroxy-13 beta-methylgona-4,9-dien-3-oneMeSH
17 alpha-Cyanomethyl-17 beta-hydroxyestra-4,9(10)-diene-3-oneMeSH
STS 557MeSH
Chemical FormulaC20H25NO2
Average Molecular Mass311.425 g/mol
Monoisotopic Mass311.189 g/mol
CAS Registry Number65928-58-7
IUPAC Name2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6-dien-14-yl]acetonitrile
Traditional Namedienogest
SMILES[H][C@@]12CC[C@@](O)(CC#N)[C@@]1(C)CCC1=C3CCC(=O)C=C3CC[C@@]21[H]
InChI IdentifierInChI=1S/C20H25NO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-10H2,1H3/t17-,18+,19+,20-/m1/s1
InChI KeyAZFLJNIPTRTECV-FUMNGEBKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • 3-oxosteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Carbonitrile
  • Nitrile
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.076 g/LALOGPS
logP3.37ALOGPS
logP2.31ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity90.19 m³·mol⁻¹ChemAxon
Polarizability35.4 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0019000000-8b6511db078a7ef4a6d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0093000000-b1ea74e40f8e85986825Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0390000000-58a5bd49692ab6bd5ef9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dl-0950000000-d53345d5771b7bff2baeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0910000000-6c64873dce18fb49e840Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1910000000-5dd58f138435ec0555a4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0009000000-f354babe14ff8cd78da5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0109000000-aa4e4dd10536f9ed7fb4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0924000000-0a4b5e59ffb5fd090a1aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0btl-1910000000-baa05a6be42e71aa9634Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4u-2900000000-d615a57fc7b003b3df8dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05ox-3900000000-17cbf8436dfbbec977c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-0094000000-50fb9a06eb8560e52822Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004m-0190000000-0fc42e05a00c5cc11513Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2590000000-b458b183bf2a40db15d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0039000000-39c1ac37c43ebac14128Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1097000000-fab8ad63447a45f0c3b8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2090000000-bb7a2a43f4e20b357256Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2671.0Log mg/kg[1500:4800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
317Hormonal contraceptives for systemic useHealthcare, pharmaceuticals & veterinary productsNot Available
320ProgestogensHealthcare, pharmaceuticals & veterinary productsNot Available
322Progestogens and estrogens in combinationHealthcare, pharmaceuticals & veterinary productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
Pathways
2 pathways
Dienogest Action Pathway
Dienogest Action Pathway
Dienogest Drug Metabolism Pathway
Dienogest Drug Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)5.68299
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)6.07224
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)13.8572
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)16.8933
Click to view 3D structureGlucocorticoid receptorQ9N1U3Sus scrofaPredicted (SEA)1.79053
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)16.2705
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)9.6533
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)455.807
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)6.15009
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)63.3693
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)60.2553
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)481.887
Click to view 3D structureSex hormone-binding globulinP08689Rattus norvegicusPredicted (SEA)0.622794
Click to view 3D structureGlucocorticoid receptorP06537Mus musculusPredicted (SEA)3.58106
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)17.9053
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)84.8557
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)431.363
Click to view 3D structureProgesterone receptorQ63449Rattus norvegicusPredicted (SEA)0.233548
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)48.1108
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)22.4984
Click to view 3D structureGlucocorticoid receptorA0A8C0QLS2Canis lupus familiarisPredicted (SEA)1.94623
Thyroid hormone receptor beta structureClick to view 3D structureThyroid hormone receptor betaP10828HumansPredicted (SEA)85.0892
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)1562.9
Thyroid hormone receptor alpha structureClick to view 3D structureThyroid hormone receptor alphaP10827HumansPredicted (SEA)54.5723
Click to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)29.427
Concentrations
Not Available
External Links
DrugBank IDDB09123
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDienogest
Chemspider IDNot Available
ChEBI ID70708
PubChem Compound ID68861
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21681516
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22003899
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22067805
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22130322
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22149760
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22160205
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22169052
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22264663
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22322156
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22364708
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22366992
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22413833
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22445438
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22459918
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22515510
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22571602
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22876102
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22878119
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23003209