Sex Hormones Medicinal Chemistry – PPT

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3 months ago

Sex hormones: Testosterone, Nandralone, Progestrones, Oestriol, Oestradiol, Oestrione,
Diethyl stilbestrol.

Sex Hormones ppt

Definition: Sex hormones are steroid hormones produced primarily by the gonads (testes and ovaries) that regulate reproductive functions and secondary sexual characteristics.
Classification:
1. Androgens: Male sex hormones
2. Estrogens: Female sex hormones
3. Progestogens: Hormones involved in the menstrual cycle and pregnancy

Chemical Structure: Testosterone is a steroid hormone derived from cholesterol. It has a cyclopentanoperhydrophenanthrene ring structure typical of steroid hormones.
Functions:
- Promotes development of male reproductive organs.
- Stimulates muscle growth and secondary male characteristics.
- Regulates libido and bone mass.
Clinical Applications:
- Used in testosterone replacement therapy for hypogonadism.
- Also used for muscle wasting disorders.
SAR Note: Modifications on the A-ring and 17-position influence its anabolic and androgenic activity.

Chemical Structure: Nandrolone is a synthetic anabolic steroid structurally similar to testosterone, with a missing carbon at the 19-position.
Functions:
- Strong anabolic effects, promoting muscle mass and bone density.
- Weak androgenic activity compared to testosterone.
Clinical Applications:
- Used in the treatment of anemia and osteoporosis.
- Prescribed for wasting syndromes associated with chronic diseases.
SAR Note: Removal of the methyl group at C-19 reduces androgenic effects while maintaining anabolic properties.

Chemical Structure: Progesterone is a C21 steroid hormone with a 4,5-diene structure and a ketone group at the 3-position.
Functions:
- Regulates the menstrual cycle and maintains pregnancy.
- Prepares the endometrium for implantation.
- Prevents uterine contractions during pregnancy.
Clinical Applications:
- Used in hormone replacement therapy (HRT) and oral contraceptives.
- Treats conditions like amenorrhea and endometriosis.
SAR Note: The presence of a keto group at C-3 and a double bond at C-4 are critical for progesterone activity.

Chemical Structure: Estradiol is the most potent natural estrogen, with a phenolic A-ring and a hydroxyl group at the 17-beta position.
Functions:
- Promotes development of female secondary sexual characteristics.
- Regulates the menstrual cycle and maintains bone health.
- Plays a key role in fertility and ovulation.
Clinical Applications:
- Used in HRT and contraceptives.
- Treats menopausal symptoms and osteoporosis.
SAR Note: The hydroxyl groups at C-3 and C-17 are critical for estrogenic activity.

Chemical Structure: Estrone is a less potent estrogen with a ketone group at the C-17 position instead of a hydroxyl group.
Functions:
- Weaker estrogen compared to estradiol.
- Predominant estrogen in postmenopausal women.
Clinical Applications:
- Used in menopausal therapy, especially in estrogen-deficient conditions.
- Acts as a precursor to estradiol in the body.
SAR Note: The keto group at C-17 results in lower potency compared to estradiol.

Chemical Structure: Estriol has hydroxyl groups at C-3, C-16, and C-17, making it the weakest natural estrogen.
Functions:
- Main estrogen produced during pregnancy.
- Plays a role in maintaining pregnancy by regulating the uteroplacental blood flow.
Clinical Applications:
- Primarily used in HRT for postmenopausal women.
- Potential protective role against breast cancer in some studies.
SAR Note: The triple hydroxyl groups reduce its potency and estrogenic activity.

Chemical Structure: Diethylstilbestrol is a synthetic non-steroidal estrogen with two aromatic rings connected by an ethylene bridge.
Functions:
- Mimics the effects of natural estrogens like estradiol.
Clinical Applications:
- Previously used in preventing miscarriages (now discontinued due to risks).
- Occasionally used in certain estrogen-deficient states and prostate cancer therapy.
SAR Note: DES is more stable than natural estrogens, but its prolonged use is associated with an increased risk of cancer.

Androgens (Testosterone, Nandrolone): Regulate male sexual development, muscle mass, and bone density.
Progestogens (Progesterone): Key for pregnancy maintenance and menstrual cycle regulation.
Estrogens (Estradiol, Estrone, Estriol): Regulate female reproductive function, promote bone health, and are crucial in pregnancy.
Synthetic Estrogens (Diethylstilbestrol): Previously used for pregnancy-related issues, but with significant side effects.

Testosterone/Nandrolone: Hormone replacement, muscle wasting diseases.
Progesterone: Oral contraceptives, HRT, reproductive disorders.
Estrogens (Estradiol, Estrone, Estriol): Menopausal therapy, osteoporosis, contraception.
Diethylstilbestrol: Historical use in pregnancy complications and cancer therapy.

Key Takeaways:
- Sex hormones play a critical role in regulating reproductive functions and secondary sexual characteristics.
- Understanding their structure-activity relationships (SAR) helps in optimizing clinical therapies.
- Caution is required when using synthetic hormones like DES due to potential side effects.

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