Pregnane
Encyclopedia
Pregnane is, indirectly, a parent of progesterone
. It is a parent hydrocarbon
for two series of steroid
s stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyletiocholane).
5β-Pregnane is the parent of the progesterone
s, pregnane alcohols, ketone
s, and several adrenocortical hormones and is found largely in urine
as a metabolic
product of 5β-pregnane compounds
.
derivatives with carbons present at positions 1 through 21.
Most biologically significant pregnane derivatives fall into one of two groups: pregnenes and pregnadiene
s. Another class is pregnatrienes.
Pregnenes have a double bond
. Examples include:
Pregnadienes have two double bonds. Examples include:
Progesterone
Progesterone also known as P4 is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species...
. It is a parent hydrocarbon
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
for two series of steroid
Steroid
A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...
s stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyletiocholane).
5β-Pregnane is the parent of the progesterone
Progesterone
Progesterone also known as P4 is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species...
s, pregnane alcohols, ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
s, and several adrenocortical hormones and is found largely in urine
Urine
Urine is a typically sterile liquid by-product of the body that is secreted by the kidneys through a process called urination and excreted through the urethra. Cellular metabolism generates numerous by-products, many rich in nitrogen, that require elimination from the bloodstream...
as a metabolic
Metabolism
Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...
product of 5β-pregnane compounds
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
.
Pregnanes
Pregnanes are steroidSteroid
A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...
derivatives with carbons present at positions 1 through 21.
Most biologically significant pregnane derivatives fall into one of two groups: pregnenes and pregnadiene
Pregnadiene
A pregnadiene is a diene derivative of a pregnane.Dienes have two double bonds. The first is usually between carbon 4 and carbon 5 on ring A....
s. Another class is pregnatrienes.
Pregnenes
Double bond
A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...
. Examples include:
- CortisoneCortisoneCortisone is a steroid hormone. It is one of the main hormones released by the adrenal gland in response to stress. In chemical structure, it is a corticosteroid closely related to corticosterone. It is used to treat a variety of ailments and can be administered intravenously, orally,...
- Hydrocortisone
- ProgesteroneProgesteroneProgesterone also known as P4 is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species...
Pregnadienes
- CyproteroneCyproteroneCyproterone acetate is an antiandrogen...
- DanazolDanazolDanazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. Also known as 17alpha-ethinyl testosterone. Before becoming available as a generic drug, Danazol was marketed as Danocrine in the United States. It was approved by the U.S. Food and Drug Administration as the...
- FluocinonideFluocinonideFluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema and seborrhoeic dermatitis...