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Azastene (
One synthesis of this compound involves initial alkylation of methyl testosterone by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative. Formylation with alkoxide and methyl formate leads to the 2-hydroxymethyl derivative. Reaction of this last with hydroxylamine leads to formation of an isoxazole ring. There is then obtained azastene.
INN
Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...
, USAN) (developmental code name WIN-17625) is a steroidogenesis inhibitor described as a contraceptive
Birth control, also known as contraception, anticonception, and fertility control, is the use of methods or devices to prevent unwanted pregnancy. Birth control has been used since ancient times, but effective and safe methods of birth contr ...
, luteolytic, and abortifacient
An abortifacient ("that which will cause a miscarriage" from Latin: ''abortus'' "miscarriage" and '' faciens'' "making") is a substance that induces abortion. This is a nonspecific term which may refer to any number of substances or medications, ...
which was never marketed. It acts as a competitive inhibitor of 3β-hydroxysteroid dehydrogenase ( IC50 = 1 μM), and thereby inhibiting the formation
Formation may refer to:
Linguistics
* Back-formation, the process of creating a new lexeme by removing or affixes
* Word formation, the creation of a new word by adding affixes
Mathematics and science
* Cave formation or speleothem, a secondar ...
of progesterone
Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the m ...
, corticosteroid
Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are involv ...
s, androgens, and estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...
s. Due to inhibition of corticosteroid synthesis, azastene is immunosuppressive.
Synthesis
One synthesis of this compound involves initial alkylation of methyl testosterone by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative. Formylation with alkoxide and methyl formate leads to the 2-hydroxymethyl derivative. Reaction of this last with hydroxylamine leads to formation of an isoxazole ring. There is then obtained azastene.
See also
*Cyanoketone
Cyanoketone, also known as 2α-cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one (CTM), is a synthetic compound, synthetic androstane steroid and a steroidogenesis inhibitor which is used in scientific research. On account of its chemical struc ...
References
3β-Hydroxysteroid dehydrogenase inhibitors Androstanes Isoxazoles {{steroid-stub