6,6-Difluoronorethisterone acetate

A synthetic progestogen

6,6-Difluoronorethisterone acetate
Chemical nomenclature
IUPAC name	(8R,9S,10R,13S,14S,17S)-17-acetyl-6,6-difluoro-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

6,6-Difluoronorethisterone acetate is a synthetic progestogen that is derived from norethisterone. It is a member of the steroid class of compounds and is used in hormonal contraception and hormone replacement therapy.

Chemical structure and properties

6,6-Difluoronorethisterone acetate is a fluorinated steroid with the chemical formula C₂₂H₂₇F₂O₃. The presence of two fluorine atoms at the 6,6 position of the norethisterone backbone enhances its progestogenic activity and alters its pharmacokinetics.

Mechanism of action

As a progestogen, 6,6-Difluoronorethisterone acetate binds to the progesterone receptor in target tissues. This binding leads to changes in gene expression that mimic the effects of endogenous progesterone. These effects include the regulation of the menstrual cycle, maintenance of pregnancy, and modulation of ovulation.

Clinical uses

6,6-Difluoronorethisterone acetate is primarily used in contraceptive pills and hormone replacement therapy formulations. Its enhanced stability and activity make it a suitable candidate for these applications, providing effective contraception and alleviating symptoms of menopause.

Pharmacokinetics

The pharmacokinetics of 6,6-Difluoronorethisterone acetate involve its absorption, distribution, metabolism, and excretion. The fluorine atoms increase its lipophilicity, allowing for better absorption and distribution in the body. It is metabolized in the liver and excreted primarily through the urinary system.

Side effects

Common side effects of 6,6-Difluoronorethisterone acetate include nausea, headache, breast tenderness, and mood changes. Long-term use may be associated with an increased risk of thromboembolic events and breast cancer.

Related pages

• Norethisterone
• Progestogen
• Hormonal contraception
• Hormone replacement therapy

6,6-Difluoronorethisterone acetate

• 
  6,6-Difluoronorethisterone acetate structure