Norpregnane

Norpregnane is a type of steroid and a derivative of pregnane. It is a parent structure for a variety of biologically active compounds including progestogens, glucocorticoids, and mineralocorticoids. Norpregnanes are characterized by the absence of a methyl group at the C-19 position in the pregnane skeleton.

Structure and Nomenclature

The term "norpregnane" is derived from the word "pregnane" with the prefix "nor-" indicating the absence of a methyl group at the C-19 position. This structural modification results in a steroid with 18 carbons, compared to the 21 carbons found in pregnane. The systematic name for norpregnane is 10β,13β-dimethyl-17β-ethyl-gonane.

Biological Significance

Norpregnanes serve as the structural basis for a variety of biologically active compounds. These include progestogens, glucocorticoids, and mineralocorticoids, which play crucial roles in various physiological processes.

Progestogens are a class of hormones that maintain pregnancy and prevent ovulation. They are synthesized from norpregnane derivatives in the body. Some synthetic progestogens, such as medroxyprogesterone acetate and megestrol acetate, are also based on the norpregnane structure.

Glucocorticoids are a type of steroid hormone that regulate metabolism and immune response. They are synthesized from norpregnane derivatives in the adrenal glands. Synthetic glucocorticoids, such as prednisone and dexamethasone, are used in medicine to treat a variety of conditions including inflammation and autoimmune diseases.

Mineralocorticoids are a class of steroid hormones that regulate salt and water balance in the body. They are synthesized from norpregnane derivatives in the adrenal glands. The most important mineralocorticoid is aldosterone, which helps control blood pressure and the balance of electrolytes in the body.

See Also

• Steroid
• Pregnane
• Progestogen
• Glucocorticoid
• Mineralocorticoid