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Evidence for the metabolic lability of the C-21 hydrogens of corticosteroids.

A study of the metabolism of the corticosteroid side-chain has been initiated with steroids tritiated at position 21. When 21-3H cortisol or 21-3H-11-deoxycorticosterone was injected into hamsters, tritium from the steroid was incorporated into water in all tissues examined. Tritium from labeled deoxycorticosterone was incorporated into water faster than from labeled cortisol by liver in vitro. 11-Deoxysteroids were detritiated more rapidly than 11β-hydroxylated steroids. The 21S-21-3H enantiomeric forms of the steroids were detritiated faster than the 21R-21-3H forms. It was concluded that the protons at position 21 of corticosteroids are metabolically labile and are converted to water by a process which shows stereospecific selectivity.