17α-methylprogesterone
17α-Methylprogesterone[edit | edit source]
17α-Methylprogesterone is a synthetic progestogen, a type of hormone that mimics the effects of progesterone in the body. It is a derivative of progesterone with a methyl group added at the 17α position, which alters its pharmacokinetic properties and enhances its oral bioavailability.
Chemical Structure and Properties[edit | edit source]
17α-Methylprogesterone is a steroid with the chemical formula C22H32O2. The addition of a methyl group at the 17α position distinguishes it from natural progesterone, affecting its interaction with the progesterone receptor and its metabolic stability.
Mechanism of Action[edit | edit source]
As a progestogen, 17α-methylprogesterone binds to the progesterone receptor, which is a type of nuclear receptor. Upon binding, it influences the transcription of specific genes that regulate the menstrual cycle, pregnancy, and embryogenesis. It also has effects on the endometrium, making it suitable for use in hormonal contraception and hormone replacement therapy.
Clinical Uses[edit | edit source]
17α-Methylprogesterone has been used in various clinical settings, including:
- **Contraception**: As a component of oral contraceptives, it helps prevent ovulation and alters the uterine lining to prevent implantation.
- **Hormone Replacement Therapy (HRT)**: Used in combination with estrogens to alleviate symptoms of menopause and reduce the risk of endometrial cancer.
- **Gynecological Disorders**: It may be used to treat conditions such as endometriosis and dysmenorrhea.
Pharmacokinetics[edit | edit source]
The methylation at the 17α position increases the oral bioavailability of 17α-methylprogesterone compared to natural progesterone, which is rapidly metabolized in the liver. This modification allows for effective oral administration.
Side Effects[edit | edit source]
Common side effects of 17α-methylprogesterone include:
Long-term use may be associated with an increased risk of thromboembolic events and breast cancer.
History[edit | edit source]
17α-Methylprogesterone was developed in the mid-20th century as part of efforts to create orally active progestogens. It was one of the first synthetic progestogens used in oral contraceptives.
Also see[edit | edit source]
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