2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-1,6-dien-14-yl]acetonitrile

• ChemBase ID: 72593
• Molecular Formular: C20H25NO2
• Molecular Mass: 311.418
• Monoisotopic Mass: 311.18852905
• SMILES: C1(=O)CCC2=C3[C@@H](CCC2=C1)[C@@H]1CC[C@@]([C@@]1(C)CC3)(O)CC#N
• Canonical SMILES: N#CC[C@]1(O)CC[C@@H]2[C@]1(C)CCC1=C3CCC(=O)C=C3CC[C@@H]21
• InChI: InChI=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
• InChIKey: AZFLJNIPTRTECV-FUMNGEBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-14-yl]acetonitrile; 2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-14-yl]acetonitrile
• IUPAC Traditional name: dienogest
• Synonyms: (17α)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile; 17α-Cyanomethyl-17β-hydroxyestra-4, 9-dien-3-one; Dienogestril; Endometrion; STS 557; Natazia; Dienogest

Database IDs

• CAS Number: 65928-58-7
• PubChem SID: 162037518
• PubChem CID: 68861

CALCULATED PROPERTIES

• Acid pKa: 13.782009
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.3128524
• LogD (pH = 7.4): 2.3128524
• Log P: 2.3128524
• Molar Refractivity: 90.191 cm^3
• Polarizability: 34.700165 Å^3
• Polar Surface Area: 61.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Pyridine
• Apperance: Pale Yellow Solid
• Melting Point: 210-214°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Pharmacology Properties

• Target: Progesterone

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1251

Research Area: Metrorrhagia
Biological Activity:
Dienogest is an orally active synthetic progesterone (or progestin). It is available for use as an oral contraceptive in combination with ethinylestradiol. It has antiandrogenic activity and as a result can improve androgenic symptoms. It is a non-ethinylated progestin which is structurally related to testosterone. [1] 

Toronto Research Chemicals - D441870

Derivative of 19-Nortestosterone. In combination with estrogen as oral contraceptive. Progestogen.

REFERENCES

• http://en.wikipedia.org/wiki/Dienogest
• Hubner, M., et al.: Arzneim.-Forsch., 30, 401 (1980)
• Spona, J., et al.: Contraception, 56, 185 (1980)
• Foster, R.H., et al.: Drugs, 56, 825 (1980)