Pregnanes
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Pregnanes
Pregnane, also known as 17β-ethylandrostane or as 10β,13β-dimethyl-17β-ethylgonane, is a C21 steroid and, indirectly, a parent of progesterone. It is a parent hydrocarbon for two series of steroids stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyl etiocholane). It has a gonane core. 5β-Pregnane is the parent of pregnanediones, pregnanolones, and pregnanediols, and is found largely in urine as a metabolic product of 5β-pregnane compounds. Pregnanes Pregnanes are steroid derivatives with carbons present at positions 1 through 21. Most biologically significant pregnane derivatives fall into one of two groups: pregnenes and pregnadienes. Another class is pregnatrienes. Pregnenes Pregnenes have a double bond. Examples include: * Cortisone * Hydrocortisone * Progesterone Pregnadienes Pregnadienes have two double bonds. Examples include: * Cyproterone acetate * Danazol Danazol, sold as Danocrine and other brand names, is a me ...
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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 17β-ethylandrostane or as 10β,13β-dimethyl-17β-ethylgonane, is a C21 steroid and, indirectly, a parent of progesterone. It is a parent hydrocarbon for two series of steroids stemming from 5α-pregnane (originally all ... Pregnanes {{steroid-stub ...
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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 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 ... (pregn-4-ene-3,20-dione) * Pregnanolone * Pregnanediol * Pregnanetriol * Pregna-4,20-dien-3,6-dione * Hydroxyprogesterone References Pregnanes {{Chemistry index ...
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Cortisone Structure
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 isozyme 2 into the inactive metabolite cortisone, particularly in the kidneys. This is done by oxidizing the alcohol group at carbon 11 (in the six-membered ring fused to the five-membered ring). Cortisone is converted back to the active steroid cortisol by stereospecific hydrogenation at carbon 11 by the enzyme 11β-Hydroxysteroid dehydrogenase type 1, particularly in the liver. The term "cortisone" is frequently misused to mean either any corticosteroid or hydrocortisone, which is in fact cortisol. Many who speak of receiving a "cortisone shot" or taking "cortisone" are more likely receiving hydrocortisone or one of many other, much more potent synthetic corticosteroids. Cortisone can be administered as a prodrug, meaning it has to be con ...
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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 isozyme 2 into the inactive metabolite cortisone, particularly in the kidneys. This is done by oxidizing the alcohol group at carbon 11 (in the six-membered ring fused to the five-membered ring). Cortisone is converted back to the active steroid cortisol by stereospecific hydrogenation at carbon 11 by the enzyme 11β-Hydroxysteroid dehydrogenase type 1, particularly in the liver. The term "cortisone" is frequently misused to mean either any corticosteroid or hydrocortisone, which is in fact cortisol. Many who speak of receiving a "cortisone shot" or taking "cortisone" are more likely receiving hydrocortisone or one of many other, much more potent synthetic corticosteroids. Cortisone can be administered as a prodrug, meaning it has to ...
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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, adrenogenital syndrome, high blood calcium, thyroiditis, rheumatoid arthritis, dermatitis, asthma, and COPD. It is the treatment of choice for adrenocortical insufficiency. It can be given by mouth, topically, rectally or by injection. Stopping treatment after long-term use should be done slowly. Common side effects may include mood changes, increased appetite, hyperglycemia, hypertension, and edema (swelling). With long-term use, common side effects include osteoporosis, adrenal insufficiency, upset stomach, physical weakness, easy bruising, and candidiasis (yeast infections). It is unclear if it is safe for use during pregnancy. Hydrocortisone was patented in 1936 and approved for medical use in 1941. It is on the World Health Orga ...
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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 urine of pregnant women from London clinics, Guy Frederic Marrian isolated a substance that contained two hydroxyl groups and could be converted into a diacetate with acetic anhydride. However, the formula had not been clearly clarified. Almost at the same time, Adolf Butenandt at the Chemical University Laboratory in Göttingen investigated the constituents of pregnant urine and clarified the structure of the diol. The name pregnandiol, coined by Butenandt, is derived from the Latin verb praegnans (pregnant) or the English pregnant and pregnancy. This gave rise to the name pregnane for the underlying parent hydrocarbon. In 1936, Venning and Browne demonstrated the presence of pregnanediol, specifically the glucuronide of pregnanediol in pr ...
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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 positive allosteric modulator of the GABAA receptor, as well as a negative allosteric modulator of the glycine receptor. Biological function Pregnanolone has sedative, anxiolytic, anesthetic, and anticonvulsant effects. During pregnancy, pregnanolone and allopregnanolone are involved in sedation and anesthesia of the fetus. Biochemistry Pregnanolone is synthesized from progesterone via the enzymes 5β-reductase and 3α-hydroxysteroid dehydrogenase, with 5β-dihydroprogesterone occurring as a metabolic intermediate. The elimination half-life of pregnanolone is between 0.9 and 3.5 hours. Chemistry Pregnanolone, also known as 3α,5β-tetrahydroprogesterone (3α,5β-THP) or as 5β-pregnan-3α-ol-20-one, is a naturally occurring pregn ...
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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 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 ... (pregn-4-ene-3,20-dione) * Pregnanolone * Pregnanediol * Pregnanetriol * Pregna-4,20-dien-3,6-dione * Hydroxyprogesterone References Pregnanes {{Chemistry index ...
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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 major progestogen in the body. Progesterone has a variety of important functions in the body. It is also a crucial metabolic intermediate in the production of other endogenous steroids, including the sex hormones and the corticosteroids, and plays an important role in brain function as a neurosteroid. In addition to its role as a natural hormone, progesterone is also used as a medication, such as in combination with estrogen for contraception, to reduce the risk of Uterine cancer, uterine or cervical cancer, in hormone replacement therapy, and in feminizing hormone therapy. It was first prescribed in 1934. Biological activity Progesterone is the most important progestogen in the body. As a potent agonist of the progesterone receptor, nu ...
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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 treatment of androgen-dependent conditions such as acne, hirsutism, excessive body hair growth, precocious puberty, early puberty, and prostate cancer, as a component of feminizing hormone therapy for Transgender, transgender individuals, and in oral contraceptive, birth control pills. It is formulated and used both alone and in combination with an estrogen (medication), estrogen. CPA is taken Oral administration, by mouth one to three times per day. Common side effects of high-dose CPA in men include gynecomastia (breast development) and feminization (biology), feminization. In both men and women, possible side effects of CPA include hypogonadism, low sex hormone levels, reversible infertility, sexual dysfunction, fatigue (medical), fatigue ...
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