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Stereoselective Inhibition of Aromatase by Enantiomers of Aminoglutethimide^*

P. E. GRAVES and H. A. SALHANICK

Department of Population Sciences, Harvard School of Public Health, and the Department of Obstetrics and Gynecology Harvard Medical School Boston, Massachusetts 02115

Address requests for reprints to: H. A. Salhanick, Ph.D., M.D., Department of Population Sciences, Harvard School of Public Health, 665 Huntington Avenue, Boston, Massachusetts 02115.

Abstract

The dextrorotatory enantiomer of aminoglutethimide is 38 times more potent than the levoenantiomer in inhibiting aromatization of testosterone by human placental microsomes. The spectral affinity constant for microsomal cytochrome P-450 is 36 times greater for the d-enantiomer. Enzymatic inhibition and affinity are highly correlated for each of the isomers as well as for the racemic mixture. Spectral analysis of the interactions of the inhibitors with the substrate supports the evidence for participation of cytochrome P-450 in aromatization.

Footnotes

^* This work was supported in part by USPHS Grant AM-10081 and NICHHD Contract NIH-70-2319.

Current address: University of Arizona Health Sciences Center, Department of Internal Medicine, Tucson, Arizona 85724.

Received November 30, 1978.

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