Top Qs
Timeline
Chat
Perspective
Paroxypropione
Chemical compound From Wikipedia, the free encyclopedia
Remove ads
Paroxypropione, also known as paraoxypropiophenone, is a synthetic nonsteroidal estrogen which has been used medically as an antigonadotropin in Spain and Italy but appears to no longer be marketed.[1][2][3][4] It was first synthesized in 1902.[1] The antigonadotropic properties of the drug were discovered in 1951[3] and it entered clinical use shortly thereafter.[5]
Remove ads
Pharmacology
Pharmacodynamics
Paroxypropione is closely related structurally to p-hydroxybenzoic acid and parabens such as methylparaben, and also bears a close resemblance to diethylstilbestrol (which, in fact, produces paroxypropione as an active metabolite)[6][7] and alkylphenols like nonylphenol, all of which are also estrogens.[8][9] The drug possesses relatively low affinity for the estrogen receptor[4] and must be given at high dosages to achieve significant estrogenic and antigonadotropic effects, for instance, 0.8 to 1.6 g/day.[10][11] It possesses 0.1% of the estrogenic activity and less than 0.5% of the antigonadotropic potency of estrone.[12]
Remove ads
Chemistry
Synthesis
The highest reported yield, approximately 96%, is from the between phenol and propionyl chloride.[13] The mechanism is likely to involve initial esterification to give phenyl propionate, which then undergoes a Fries rearrangement.
Derivatives
Paroxypropione is a precursor in the chemical synthesis of diethylstilbestrol and dienestrol.[14][15]
Society and culture
Names
Brand names Frenantol, Frenormon, Hypophenon, Paroxon, Possipione, Profenone, numerous others; former developmental code name NSC-2834, also known as paroxypropiophenone (P.O.P.) or 4'-hydroxypropiophenone.
Research
Paroxypropione was studied and used in the treatment of breast cancer.[16][17][18]
References
Further reading
Wikiwand - on
Seamless Wikipedia browsing. On steroids.
Remove ads