Stereochemistry of Steroid Drugs:
Stereochemistry of steroid drugs studies the 3D arrangement of atoms that influences their biological activity and effects.
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.
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Key Stereochemical Features:
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Alpha (α) and Beta (β) Configurations:
- Define the orientation of functional groups relative to the steroid nucleus.
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Double Bonds and Rings:
- Δ4, Δ5, Δ9, etc.: Indicate the position of double bonds, influencing drug activity and metabolism.
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Substituent Positions:
- C17α vs. C17β: Placement of hydroxyl or other groups at carbon 17 affects potency and receptor affinity.
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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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