Pregnane X Receptor Agonists
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Pregnane, also known as 17β-ethylandrostane or as 10β,13β-dimethyl-17β-ethylgonane, is a C21
steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...
and, indirectly, a
parent A parent is either the progenitor of a child or, in humans, it can refer to a caregiver or legal guardian, generally called an adoptive parent or step-parent. Parents who are progenitors are First-degree relative, first-degree relatives and have ...
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 ma ...
. It is a parent
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
for two series of steroids stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyl etiocholane). It has a
gonane Gonane (cyclopentanoperhydrophenanthrene) is a chemical compound with formula , whose structure consists of four hydrocarbon rings fused together: three cyclohexane units and one cyclopentane. It can also be viewed as the result of fusing a cyc ...
core. 5β-Pregnane is the parent of
pregnanedione Pregnanedione, or pregnane-3,20-dione, may refer to: * 5α-Dihydroprogesterone (5α-pregnane-3,20-dione) * 5β-Dihydroprogesterone (5β-pregnane-3,20-dione) See also * Progesterone Progesterone (; P4) is an endogenous steroid and progestog ...
s,
pregnanolone Pregnanolone, also known as eltanolone, is an endogenous inhibitory neurosteroid which is produced in the body from progesterone. It is closely related to allopregnanolone, which has similar properties. Biological activity Pregnanolone is a pos ...
s, and
pregnanediol Pregnanediol, or 5β-pregnane-3α,20α-diol, is an inactive metabolic product of progesterone. A test can be done to measure the amount of pregnanediol in urine, which offers an indirect way to measure progesterone levels in the body. From the ur ...
s, and is found largely in
urine Urine is a liquid by-product of metabolism in humans and many other animals. In placental mammals, urine flows from the Kidney (vertebrates), kidneys through the ureters to the urinary bladder and exits the urethra through the penile meatus (mal ...
as a
metabolic Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the ...
product of 5β-pregnane
compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struc ...
s.


Pregnanes

Pregnanes are
steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...
derivatives with carbons present at positions 1 through 21. Most biologically significant pregnane derivatives fall into one of two groups:
pregnene A pregnene is an alkene derivative of a pregnane. An example is cortisone. Image:Cortison.svg, Cortisone Image:Ethisterone.png, Ethisterone Image:Spironolacton.svg, Spironolactone References See also * Pregnanes Pregnane, also known as ...
s and
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. 6-ene The second can be between carbons 6 and 7 on ring B: File:Chlormadinone_acetate.svg, Chlormadin ...
s. Another class is
pregnatriene A pregnatriene is a triene derivative of a pregnane. An example is cortivazol. References See also * Pregnane Pregnanes Polyenes {{steroid-stub ...
s.


Pregnenes

Pregnenes have a
double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...
. Examples include: *
Cortisone Cortisone is a pregnene (21-carbon) steroid hormone. It is a naturally-occurring corticosteroid metabolite that is also used as a pharmaceutical prodrug. Cortisol is converted by the action of the enzyme corticosteroid 11-beta-dehydrogenase ...
*
Hydrocortisone Hydrocortisone is the name for the hormone cortisol when supplied as a medication. It is a corticosteroid and works as an anti-inflammatory and by immune suppression. Uses include conditions such as adrenocortical insufficiency, adrenogenit ...
*
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 ma ...


Pregnadienes

Pregnadienes have two
double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...
s. Examples include: *
Cyproterone acetate Cyproterone acetate (CPA), sold alone under the brand name Androcur or Ethinylestradiol/cyproterone acetate, with ethinylestradiol under the brand names Diane or Diane-35 among others, is an antiandrogen and progestin medication used in the tre ...
*
Danazol Danazol, sold as Danocrine and other brand names, is a medication used in the treatment of endometriosis, fibrocystic breast disease, hereditary angioedema and other conditions. It is taken oral administration, by mouth. The use of danazol is ...
*
Fluocinonide Fluocinonide is a potent glucocorticoid used topically as an anti-inflammatory agent for the treatment of skin disorders such as eczema and seborrhoeic dermatitis. It relieves itching, redness, dryness, crusting, scaling, inflammation ...


See also

* 5β-Pregnane *
Pregnanedione Pregnanedione, or pregnane-3,20-dione, may refer to: * 5α-Dihydroprogesterone (5α-pregnane-3,20-dione) * 5β-Dihydroprogesterone (5β-pregnane-3,20-dione) See also * Progesterone Progesterone (; P4) is an endogenous steroid and progestog ...
*
Pregnanediol Pregnanediol, or 5β-pregnane-3α,20α-diol, is an inactive metabolic product of progesterone. A test can be done to measure the amount of pregnanediol in urine, which offers an indirect way to measure progesterone levels in the body. From the ur ...
* 19-Norpregnane *
Androstane Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane. File:androstane.png, 5α-Androstane File:androstane 5beta.png, 5β-Androstane Pharmacolog ...
*
Estrane Estrane is a C18 steroid derivative, with a gonane core. ''Estrenes'' are estrane derivatives that contain a double bond, with an example being nandrolone. ''Estratrienes'' (estrins) are estrane derivatives that contain three double bonds, for i ...


References


External links

* *
PubChem



Definition of Pregnane



Progesterone record in European Bioinformatics database
Endocrinology {{steroid-stub