Clomegestone acetate: Difference between revisions

Latest revision as of 05:34, 16 February 2025

Clomegestone Acetate[edit]

Clomegestone acetate is a synthetic progestin of the pregnane group, which is used in hormonal contraception and hormone replacement therapy. It is a derivative of progesterone, a naturally occurring hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species.

Chemical Properties[edit]

Clomegestone acetate is a steroidal progestin, specifically a 17_-hydroxyprogesterone derivative. Its chemical structure is characterized by the presence of an acetate group, which is a common modification to enhance the bioavailability and pharmacokinetics of steroid hormones. The molecular formula of clomegestone acetate is C23H29ClO4.

Mechanism of Action[edit]

As a progestin, clomegestone acetate acts primarily on the progesterone receptor. It mimics the effects of natural progesterone by binding to these receptors in the uterus, mammary gland, and hypothalamus. This binding leads to changes in the endometrium, making it less suitable for implantation of a fertilized egg, and alters the cervical mucus to prevent sperm penetration.

Clinical Uses[edit]

Clomegestone acetate is used in various contraceptive formulations, often in combination with an estrogen such as ethinylestradiol. It is also used in hormone replacement therapy for menopausal symptoms. The combination of clomegestone acetate with estrogen helps to prevent endometrial hyperplasia that can occur with estrogen therapy alone.

Side Effects[edit]

The side effects of clomegestone acetate are similar to those of other progestins and may include nausea, breast tenderness, headache, and mood changes. Long-term use of progestins has been associated with an increased risk of thromboembolic events and breast cancer.

Pharmacokinetics[edit]

Clomegestone acetate is administered orally and is well absorbed from the gastrointestinal tract. It undergoes hepatic metabolism and is excreted primarily in the urine. The acetate ester is hydrolyzed to the active form, clomegestone, which exerts the progestogenic effects.

Related Pages[edit]

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-'''Clomegestone acetate''', also known by its developmental code name '''SH-741''', is a synthetic [[progestogen]] that was never marketed. It is a derivative of [[progesterone]], specifically a combined derivative of [[17α-hydroxyprogesterone]] and [[chlormadinone acetate]], indicating its place within the [[17α-hydroxyprogesterone caproate]] group of progestogens. Clomegestone acetate was developed in the 1960s but, for reasons not extensively documented in the public domain, it did not progress beyond the research phase into clinical use.
+== Clomegestone Acetate ==
-==Chemistry==
+[[File:Clomegestone_acetate.svg|thumb|right|Chemical structure of Clomegestone acetate]]
-Clomegestone acetate is a [[progestin]], or a synthetic progestogen, with the chemical formula C23H29ClO4. It is closely related to other 17α-hydroxyprogesterone derivatives, sharing a core structure but differing in its functional groups which confer its unique pharmacological profile. The presence of a chlorine atom in its structure is a characteristic feature, distinguishing it from many other progestogens in its class.
-==Pharmacology==
+'''Clomegestone acetate''' is a synthetic [[progestin]] of the [[pregnane]] group, which is used in [[hormonal contraception]] and [[hormone replacement therapy]]. It is a derivative of [[progesterone]], a naturally occurring hormone involved in the [[menstrual cycle]], [[pregnancy]], and [[embryogenesis]] of humans and other species.
-As a progestogen, clomegestone acetate would have been expected to mimic the action of natural [[progesterone]], exhibiting effects such as the transformation of the [[endometrium]] to its secretory stage, maintaining pregnancy, and possibly influencing aspects of the menstrual cycle and fertility. However, detailed pharmacological data, including its potency, bioavailability, and specific effects on the reproductive system, remain sparse due to its limited development.
-==Development and History==
+== Chemical Properties ==
-Clomegestone acetate was synthesized and characterized in the 1960s as part of efforts to develop more potent and selective progestogens for use in [[hormonal contraception]] and hormone replacement therapy. Despite initial research, it did not proceed to clinical trials or commercial development. The reasons for this may include unfavorable pharmacokinetic properties, insufficient efficacy, or the emergence of more promising compounds during the same period.
-==Potential Applications and Implications==
+Clomegestone acetate is a [[steroid]]al progestin, specifically a [[17_-hydroxyprogesterone]] derivative. Its chemical structure is characterized by the presence of an acetate group, which is a common modification to enhance the [[bioavailability]] and [[pharmacokinetics]] of steroid hormones. The molecular formula of clomegestone acetate is C23H29ClO4.
-Had clomegestone acetate been further developed, it might have found applications similar to those of other progestogens, such as in contraceptive pills or in the treatment of gynecological disorders like [[endometriosis]], [[amenorrhea]], and [[dysmenorrhea]]. Its potential effects on hormone-sensitive tissues could also have made it a candidate for research into breast cancer and uterine cancer treatments.
-==Comparison with Other Progestogens==
+== Mechanism of Action ==
-Clomegestone acetate's structural and functional similarities to other 17α-hydroxyprogesterone derivatives, such as [[medroxyprogesterone acetate]] and [[megestrol acetate]], suggest it would have shared some of their therapeutic applications and side effects. However, without clinical data, such comparisons remain speculative.
-==Conclusion==
+As a progestin, clomegestone acetate acts primarily on the [[progesterone receptor]]. It mimics the effects of natural progesterone by binding to these receptors in the [[uterus]], [[mammary gland]], and [[hypothalamus]]. This binding leads to changes in the [[endometrium]], making it less suitable for [[implantation]] of a [[fertilized egg]], and alters the [[cervical mucus]] to prevent [[sperm]] penetration.
-While clomegestone acetate represents a "road not taken" in the development of progestogen-based therapies, its study contributes to the broader understanding of steroid hormone pharmacology and the quest for more effective and safer hormonal therapies. The discontinuation of its development underscores the challenges and uncertainties inherent in drug discovery and development.
+== Clinical Uses ==
+Clomegestone acetate is used in various [[contraceptive]] formulations, often in combination with an [[estrogen]] such as [[ethinylestradiol]]. It is also used in [[hormone replacement therapy]] for [[menopausal]] symptoms. The combination of clomegestone acetate with estrogen helps to prevent [[endometrial hyperplasia]] that can occur with estrogen therapy alone.
+== Side Effects ==
+The side effects of clomegestone acetate are similar to those of other progestins and may include [[nausea]], [[breast tenderness]], [[headache]], and [[mood changes]]. Long-term use of progestins has been associated with an increased risk of [[thromboembolic events]] and [[breast cancer]].
+== Pharmacokinetics ==
+Clomegestone acetate is administered orally and is well absorbed from the [[gastrointestinal tract]]. It undergoes [[hepatic metabolism]] and is excreted primarily in the [[urine]]. The acetate ester is hydrolyzed to the active form, clomegestone, which exerts the progestogenic effects.
+== Related Pages ==
+* [[Progestin]]
+* [[Hormonal contraception]]
+* [[Hormone replacement therapy]]
+* [[Progesterone]]
+* [[Steroid hormone]]
 [[Category:Progestogens]]
-[[Category:Synthetic steroids]]
+[[Category:Contraception]]
-[[Category:Abandoned drugs]]
+[[Category:Hormone replacement therapy]]
-{{medicine-stub}}