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Stereochemistry of Steroid Drugs

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Importance of Stereochemistry:

  • 3D Orientation: The spatial arrangement of atoms affects receptor binding and biological activity.

  • Chirality Centers: Steroids contain multiple chiral centers, leading to various isomers with distinct effects.

Stereochemistry of Steroid Drugs
Stereochemistry of Steroid Drugs

Key Stereochemical Features:

  • Alpha (α) and Beta (β) Configurations: 

    • Define the orientation of functional groups relative to the steroid nucleus.

  • Double Bonds and Rings:

    • Δ4, Δ5, Δ9, etc.: Indicate the position of double bonds, influencing drug activity and metabolism.

  • Substituent Positions:

    • C17α vs. C17β: Placement of hydroxyl or other groups at carbon 17 affects potency and receptor affinity.

Examples:

  • Dexamethasone vs. Betamethasone: Minor stereochemical differences lead to variations in glucocorticoid potency.

  • Testosterone vs. Dihydrotestosterone (DHT): DHT has a different stereochemistry, making it a more potent androgen.

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