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Journal of Pharmaceutical Sciences May 1975Mestranol (17alpha-ethynylestradiol 3-methyl ether), when placed on a carrier such as powdered silica gel and exposed to the atmosphere, is converted to a yellow...
Mestranol (17alpha-ethynylestradiol 3-methyl ether), when placed on a carrier such as powdered silica gel and exposed to the atmosphere, is converted to a yellow product. The compound formed was shown to be 1alpha-ethynyltetrahydro-1beta-hydroxy4 - (2 - hydroxy - 5 - methoxy - 3 - nitrophenethyl) - 7a - methyl-5(4H)-indanone. The 3-methyl ethers of three other steroids having aromatic A rings yielded products of a similar type. Identical compounds were prepared from the respective steroids by treatment with nitrating agents in acetic acid. This reaction in acetic acid is light catalyzed. An independent synthesis of a model compound, 6-(2-hydroxy-5-methoxy-3-nitrophenyl)-3-hexanone, established the position of the constituents on the aromatic ring as well as the location of the carbonyl. The mechanism proposed for the formation of these products is an initial oxidation of the 1-substituted tetralin to form a hydroperoxide, which is ionically decomposed to form a ketophenol. The phenol is then nitrated in the ortho-position.
Topics: Acetates; Calcium Phosphates; Catalysis; Chemical Phenomena; Chemistry; Chromatography, Thin Layer; Drug Stability; Light; Magnetic Resonance Spectroscopy; Mestranol; Nitrates; Nitrogen Oxides; Nitrophenols; Spectrophotometry, Ultraviolet; Urea
PubMed: 1151646
DOI: 10.1002/jps.2600640509 -
Research Communications in Chemical... Nov 1979Cellular uptake interactions between mestranol and taurocholate at concentrations between 50 and 1000 microM in the medium were studied in isolated hepatocytes. Rat...
Cellular uptake interactions between mestranol and taurocholate at concentrations between 50 and 1000 microM in the medium were studied in isolated hepatocytes. Rat liver cells exposed to medium containing mestranol and taurocholate attained up to twice as large a concentration of mestranol as those exposed to mestranol without the presence of the bile acid in medium. In contrast, taurocholate concentration in cells exposed simultaneously to taurocholate and mestranol was one fourth of the concentration in cells exposed to taurocholate alone.
Topics: Animals; In Vitro Techniques; Liver; Male; Mestranol; Rats; Taurocholic Acid; Time Factors
PubMed: 523772
DOI: No ID Found -
Southern Medical Journal Aug 1987
Topics: Estradiol; Humans; Mestranol; Weights and Measures
PubMed: 3616717
DOI: 10.1097/00007611-198708000-00045 -
British Journal of Obstetrics and... Oct 1979The serum cholesterol, triglycerides and electrophoretic lipoprotein patterns of 35 postmenopausal women, who subsequently received sequential mestranol and...
The serum cholesterol, triglycerides and electrophoretic lipoprotein patterns of 35 postmenopausal women, who subsequently received sequential mestranol and norethisterone, were compared with those of 35 premenopasual women of the same age and weight. The postmenopausal women had a significantly higher level of serum cholesterol (p less than 0.01) than the premenopausal women, and a significant reduction (p less than 0.001) occurred in this group after two months of therapy. There was no significant difference in level of serum cholesterol between the premenopausal group and the postmenopausal group receiving sequential mestranol and norethisterone for two months. The serum triglycerides were not significantly higher in the postmenopausal group but there was a significant increase (p less than 0.001) after two months of therapy. The marked alteration in lipid levels at the menopause may in part account for the great increase in coronary artery disease in postmenopausal women but whether these changes are reversible by giving hormone therapy remains speculative.
Topics: Adult; Body Weight; Cholesterol; Female; Humans; Lipoproteins; Menopause; Mestranol; Middle Aged; Norethindrone; Triglycerides
PubMed: 508663
DOI: 10.1111/j.1471-0528.1979.tb10698.x -
Internistische Praxis 1965
Topics: Chlormadinone Acetate; Contraception; Humans; Mestranol
PubMed: 14281297
DOI: No ID Found -
Archives of Ophthalmology (Chicago,... Jun 1966
Clinical Trial Randomized Controlled Trial
Topics: Aged; Clinical Trials as Topic; Glaucoma; Humans; Mestranol; Middle Aged; Norethynodrel; Placebos
PubMed: 5327793
DOI: 10.1001/archopht.1966.00970050773011 -
Journal of Reproduction and Fertility Oct 1974
Topics: Administration, Oral; Animals; Estrus; Female; Histamine; Histamine Release; Lynestrenol; Mestranol; Organ Size; Ovary; Pregnancy; Rats
PubMed: 4139257
DOI: 10.1530/jrf.0.0400459 -
Acta Diabetologica Latina 1974
Topics: Abdomen, Acute; Adolescent; Amenorrhea; Appendicitis; Carbohydrate Metabolism; Diabetes Mellitus; Diabetes Mellitus, Type 1; Diabetic Coma; Diabetic Ketoacidosis; Diagnosis, Differential; Diagnostic Errors; Female; Humans; Mestranol
PubMed: 4215270
DOI: 10.1007/BF02581312 -
Die Pharmazie Apr 1965
Topics: Chemistry Techniques, Analytical; Mestranol
PubMed: 5849310
DOI: No ID Found -
Obstetrics and Gynecology Dec 1966
Topics: Chlormadinone Acetate; Contraceptives, Oral; Drug Synergism; Female; Humans; Mestranol
PubMed: 4162518
DOI: No ID Found