Hormonal Mestranol

Two synthetic estrogens are used in hormonal contraceptives in the United States, ethinyl estradiol (EE) and mestranol. Mestranol must be converted to EE in the liver to be active. It is approximately 50% less potent than EE. Most combined oral contraceptives (OCs) contain estrogen at doses of 20 to 50 meg of EE daily. The contraceptive ring produces one-half the serum concentration of EE derived from a 30-mcg OC. 

Synthetic steroid hormones retain the common steroid nucleus, but they may contain novel substituents that affect their pharmacological activity. The two most widely used synthetic steroid estrogens are ethinyl estradiol (Estinyl) and mestranol, found in oral contraceptives. Synthetic steroids containing an ethinyl substitution are metabolized more slowly. Thus, these synthetic steroid hormones have better oral absorption properties and extended biological half-lives than the natural estrogens. 

Approximately 50% of a dose of mestranol is de-methylated to form ethinyl estradiol. Ethinyl estradiol also can be deethinylated. Subsequently, the metabolism of these two synthetic estrogens proceeds by means of the same pathways as the natural steroid hormones. The principal metabolites of mestranol and ethinyl estradiol are hydroxylated derivatives that are conjugated with either glucuronic acid or sulfate. The synthetic steroid estrogens, in contrast to the natural estrogens, are excreted primarily in the feces. 

In postmenopausal women taking long-term mestranol there was a fall in the serum concentration of unbound (free) thyroxine, but it was not associated with hypothyroidism the serum concentration of thyroid-stimulating hormone was unchanged (29). 

Conflicting data concerning the effects of oral contraceptives on carbohydrate metabolism have been presented the effects are probably clinically insignificant. However, estrogen hormone replacement therapy with a sequential-type product containing mestranol and norethisterone caused significantly impaired glucose tolerance (30). 

Estradiol is one of the main female sexual hormones it is also the structural backbone for the engineering of some synthetic estrogens, such as ethynyl estradiol or mestranol, used in human hormone treatments. Both natural and synthetic estrogens are classified as endocrine disrupting chemicals (EDCs).6,362 Many of these substances and their metabolites end up in the environment where... 

Steroids, hormones, and related compounds betamethasone, dexamethasone, dienoeshol, ethinyl-oestradiol, ethynodiol diacetate, fludrocortisone, liothyronine, lynoestrenol, mestranol, norethister-one, stilboestrol, thyroxine. 

It is important to investigate the bioconcentration potential of natural hormones, such as 17 -estradiol, estrone (using or tritium labeled compounds) and synthetic hormones (e.g., mestranol, diethylstilbestrol etc.). However, the concentration in the water should be at environmental relevant concentrations (< 10 ng 1 ). 

Ethinyloestradiol, or its methylated derivative mestranol, is a satisfactory first choice for pharmacotherapy. The weaker endogenous oestrogens, oestradiol, oestrone or the conjugated equine oestrogens are preferable for physiological replacement. It remains uncertain whether all oestrogens have exactly similar hormonal and nonhormonal effects, including adverse effects. 

Purnell DC, Jones JD, Becker KL (1968) Response to parathyroid hormone infusion in primary hyperparathyroidism. J Clin Endocrinol 28 567-574 Queener SF, Bell NH (1975) Calcitonin a general survey. Metabolism 24 555-567 Roraanski B, Walczinski Z (1966) Allergy in children with struma juvenile treated with thyroid hormones. Bull Pol Med Sci Hist 9 92-94 Savel H, Madison JF, Meeker Cl (1970) Cutaneous eruptions and in vitro lymphocyte hypersensitivity associated with oral contraceptives and mestranol. Arch Dermatol 101 187-190... 

E. are used therapeutically for the treatment of menstrual disorders and menopausal problems, and as Ovulation inhibitors (see). S e synthetic steroids (see Ethinylestradiol Mestranol) and nonsteroids (see StilbestTol Hexestrol) show E. activity. [Estrogen receptors (see also Hormones) J.H. Clark E.J.Peck Monogr. Endocrinol 14 (1979) 4-36 J.Ntrr-ris et al. / BioL Chem. 270 (1995) 22777-22782]... 

Devise a synthesis of mestranol, a synthetic estrogen used in oral contraceptives, from the female sex hormone estradiol. You may use any needed organic compounds or inorganic reagents. 

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