Fluoromedroxyprogesterone acetate

Synthetic progestin

Fluoromedroxyprogesterone acetate
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CAS Number	2642-88-2
PubChem	200550
DrugBank
ChemSpider	173611
KEGG

Fluoromedroxyprogesterone acetate (FMPA) is a synthetic progestin, a type of progestogen that is used in hormonal contraception and hormone replacement therapy. It is a derivative of medroxyprogesterone acetate (MPA), with a fluorine atom added to its chemical structure, which enhances its biological activity.

Chemical Structure and Properties

Fluoromedroxyprogesterone acetate is a fluorinated derivative of medroxyprogesterone acetate, a well-known progestin. The addition of a fluorine atom at the 9α position of the steroid nucleus increases its potency and alters its pharmacokinetic properties. The chemical formula of FMPA is C₂₄H₃₁FO₄, and it has a molecular weight of 402.50 g/mol.

Mechanism of Action

As a progestin, FMPA works by binding to the progesterone receptor in target tissues. This binding mimics the effects of natural progesterone, leading to changes in the endometrium that prevent ovulation and alter the cervical mucus, making it more difficult for sperm to enter the uterus. These actions make FMPA effective as a contraceptive agent.

Pharmacokinetics

Fluoromedroxyprogesterone acetate is administered via injection, allowing for a slow release and prolonged duration of action. The fluorination of the molecule increases its lipophilicity, enhancing its ability to cross cell membranes and increasing its half-life in the body. This results in sustained levels of the drug, which is beneficial for long-term contraceptive use.

Clinical Uses

FMPA is primarily used in hormonal contraception as a long-acting injectable. It is also used in hormone replacement therapy for the management of menopausal symptoms and in the treatment of certain gynecological disorders such as endometriosis.

Side Effects

Common side effects of FMPA include changes in menstrual bleeding patterns, weight gain, and mood changes. Long-term use may be associated with a decrease in bone mineral density, similar to other progestin-only contraceptives. Patients are advised to discuss potential risks and benefits with their healthcare provider.

Related Pages

• Progestin
• Medroxyprogesterone acetate
• Hormonal contraception
• Hormone replacement therapy