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The clinically used sedative-hypnotic ethchlorvynol destroys hepatic microsomal cytochrome P-450 enzymes in a process catalyzed by the same hemoproteins. Abnormal porphyrins accumulate in the livers of phenobarbital-pretreated rats after administration of ethchlorvynol. The abnormal porphyrin fraction has been isolated and shown to consist of the four possible regioisomers of N-(5-chloro-3-ethyl-3-hydroxy-2-oxo-4-pentenyl)protoporphyrin IX. Cytochrome P-450 inactivation thus appears to result from alkylation of the prosthetic heme by the oxidatively activated acetylenic function in ethchlorvynol. The autocatalytic destruction of the hemoprotein is likely to alter the metabolism and elimination of ethchlorvynol and coadministered drugs and may be the cause of the porphyrinogenic properties of ethchlorvynol.
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
April 1983,
The Journal of biological chemistry,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
November 1980,
Molecular pharmacology,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
January 1983,
Annual review of pharmacology and toxicology,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
December 1981,
Biochemistry,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
February 1990,
Biochemical Society transactions,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
October 1989,
Xenobiotica; the fate of foreign compounds in biological systems,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
February 1997,
Nihon rinsho. Japanese journal of clinical medicine,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
March 1985,
The Journal of biological chemistry,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
January 1973,
Drug metabolism and disposition: the biological fate of chemicals,
P R Ortiz de Montellano, and
H S Beilan, and
J M Mathews
January 1986,
Advances in experimental medicine and biology,
