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Centchroman: In vitro metabolism by rat liver homogenate
Author(s) -
Ratna Sanjeev,
Roy S. K.,
Ray Suprabhat,
Kole P. L.,
Salman M.,
Madhusudan K. P.,
Sircar K. P.,
Anand N.
Publication year - 1986
Publication title -
drug development research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.582
H-Index - 60
eISSN - 1098-2299
pISSN - 0272-4391
DOI - 10.1002/ddr.430070208
Subject(s) - chemistry , in vitro , metabolism , stereochemistry , metabolite , benzene , microsome , mass spectrometry , medicinal chemistry , biochemistry , chromatography , organic chemistry
Centchroman ( trans ‐2,2‐dimethyl‐3‐phenyl‐4‐(p‐(β‐pyrrolidinoethoxy) phenyl)‐7‐methoxy chroman) (I), a postcoital antifertility agent under clinical development was extensively metabolized by rat liver homogenate in vitro. Employing field desorption mass spectrometry, high performance liquid chromatography, comparison with authentic samples, and studies with 2‐ 14 C‐Centchroman, seven metabolites have so far been characterised, which include trans ‐3‐phenyl‐4‐(p‐(β‐pyrrolidinoethoxy) phenyl)‐7‐methoxy chroman (II, 37.5%), trans ‐2,2‐dimethyl‐3‐phenyl‐4‐(p‐(β pyrrolidinoethoxy) phenyl)‐7‐hydroxy chroman (III, 2.5%), β pyrrolidino‐ethoxy benzene (IV), 2,2‐dimethyl‐4‐(p‐(hydroxy) phenyl)‐7‐methoxy chromene (V, 39.4%), trans ‐2,2‐dimethyl‐3‐phenyl‐4‐(p‐(hydroxy) phenyl)‐7‐methoxy chroman (VI, 5.8%), 2,3‐ trans ‐3,4‐ trans ‐2‐methyl‐3‐phenyl‐4‐(p‐(β‐pyrrolidinoethoxy) phenyl)‐7‐methoxy chorman (VII, 2.9%), and 2,2‐dimethyl‐4‐(p‐(β‐pyrrolidinoethoxy) phenyl)‐7‐methoxy chroman (VIII, 8.8%). Formation of metabolites V and VIII are unusual cases of dephenylation during metabolism.