Lecture 36: Medicinal Chemistry of Glucocorticoids and Mineralocorticoids | Quizlet

Corticosteroids have how many carbons?

21 carbons

What is the numbering of a steroidal ring?

see photo

The 4,5 double bond and the 3-keto group on ring A (C3) are essential for what activity?

Mineralocorticoid

AND

Glucocorticoid

An 11-beta-hydroxyl group on ring C (C11) is required for what activity?

glucocorticoid activity

A hydroxyl group on ring D (C21) seems to be a requirement for what activity?

Mineralocorticoid activity

The 17-alpha-hydroxyl group on ring D (C17) is optimal for what activity?

glucocorticoids

An additional double bond in the 1,2 position on ring A increases what activity?

Glucocorticoid activity and decreases metabolism

Fluorination at the 9-alpha position on ring B enhances the activity of what?

Both glucocorticoid and mineralocorticoid

When combined with the 1,2 double bond on ring A plus other substitutions at C16 increase the activity of what?

glucocorticoits

Substitutions at C16 DECREASE the activity of what?

mineralocorticoids

Substitutions at this position on ring B have unpredictable effects

6-alpha

Additions of side chains to C17 enhance the activity of what?

glucocorticoids