Sex Hormones Medicinal Chemistry – PPT

Sex Hormones Medicinal Chemistry – PPT

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

Sex Hormones ppt  

Introduction to Sex Hormones

  • 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

Slide 3: Testosterone

  • 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.


Slide 4: Nandrolone

  • 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.


Slide 5: Progesterone

  • 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.


Slide 6: Estradiol

  • 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.


Slide 7: Estrone

  • 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.


Slide 8: Estriol

  • 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.


Slide 9: Diethylstilbestrol (DES)

  • 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.


Slide 10: Summary of Hormone Functions

  • 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.

Slide 11: Clinical Applications Overview

  • 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.

Slide 12: Conclusion

  • 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.

Slide 13: References

  • List of key references and resources for further reading.

Sex Hormones ppt  

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