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Molecular Pharmacology, Vol 16, 729-736, Copyright © 1979 by the American Society for Pharmacology and Experimental Therapeutics

Stereochemical Characteristics of Dopamine Agonists: Molecular Structure of Bromocriptine and Structural Comparisons with Apomorphine

NORMAN CAMERMAN 1, LILIAN Y. Y. CHAN 1, and ARTHUR CAMERMAN 2

1 Biochemistry Department, University of Toronto, Toronto, Ontario, Canada M5S 1A8
2 Departments of Medicine (Neurology) and Pharmacology, University of Washington, Seattle, Wash. 98195, USA.

Crystals of bromocriptine methanesulfonate·0.5 isopropanol are monoclinic with cell dimensions a = 13.991, b = 8.296, c = 17.596 Å, beta = 97.09°, space group P21 with two formula units per cell. The structure was determined by direct phasing and Fourier methods and refined to a residual of R = 0.08. The molecule of bromocriptine consists of two different similarly-oriented substituted-polycyclic systems connected by an amide linkage whose plane is roughly perpendicular to them. The absolute configuration has been verified crystallographically. The dopamine-like portion of the molecule has been compared conformationally with the active and inactive forms of apomorphine; conclusions regarding the stereochemistry of the agonist-receptor interaction have been drawn.

Note:
ACKNOWLEDGMENT We thank Sandoz Co. (U.S.A.) for a gift of bromocriptine methanesulfonate.

Submitted on March 12, 1979
Accepted on June 5, 1979






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