Soft drugs V: Thiazolidine-type derivatives of progesterone and testosterone.

Progesterone and testosterone are natural soft drugs, but to be used as drugs, their fast and facile metabolism must be prevented and their delivery controlled. A prodrug-soft drug combination can serve this purpose. Thiazolidines of testosterone, testosterone 17-propionate and progesterone were synthesized from the reaction of cysteine alkyl esters, N-methylaminoethanethiol, and mercaptamine and their hydrochlorides with the appropriate steroids. The thiazolidines function as bioreversible derivatives of the parent steroids.

[1]  J. Thénot,et al.  Toxic agents resulting from the oxidative metabolism of steroid hormones and drugs. , 1978, Journal of toxicology and environmental health.

[2]  N Bodor,et al.  Soft drugs. 1. Labile quaternary ammonium salts as soft antimicrobials. , 1980, Journal of medicinal chemistry.

[3]  P. Ortiz de Montellano,et al.  Self-catalyzed destruction of cytochrome P-450: covalent binding of ethynyl sterols to prosthetic heme. , 1979, Proceedings of the National Academy of Sciences of the United States of America.

[4]  W. M. Schubert,et al.  An Example of SN1 Cleavage of a Sulfide1 , 1965 .

[5]  James L. Johnson,et al.  “Enamine” Derivatives of Steroidal Carbonyl Compounds. IV. Structural Considerations1 , 1956 .

[6]  G. Hook,et al.  Pulmonary metabolism of xenobiotics. , 1976, Life sciences.

[7]  R. Murphy,et al.  Leukotriene C: a slow-reacting substance from murine mastocytoma cells. , 1979, Proceedings of the National Academy of Sciences of the United States of America.