Pregnane
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Pregnane
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-ethyletiocholane). 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 * Fluocinonide See also * 5β-Pregnane * Pregnanedione * Pregna ...
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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, 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 pregnan ...
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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 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 nuclear progesterone receptor (nPR) ...
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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 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 nuclear progesterone receptor (nPR) ...
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5α-pregnane
5α-Pregnane, also known as Allopregnane or as 10β,13β-dimethyl-17β-ethyl-5α-gonane, is a steroid and a parent compound of a variety of steroid derivatives. It is one of the epimers of pregnane, the other being 5β-pregnane. Derivatives of Allopregnane include the naturally occurring steroids Allopregnanolone, Allopregnanediol, Isopregnanolone, and 5α-Dihydroprogesterone. See also * 5β-Pregnane * Etiocholane * Gonane Gonane is a chemical compound with formula , whose molecule can be described as three molecules or entities of cyclohexane and one of cyclopentane, fused in a particular way. More specifically, the molecule can be described as that of cyclohe ... References * Endocrinology {{Steroid-stub ...
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Allopregnane
5α-Pregnane, also known as Allopregnane or as 10β,13β-dimethyl-17β-ethyl-5α-gonane, is a steroid and a parent compound of a variety of steroid derivatives. It is one of the epimers of pregnane, the other being 5β-pregnane. Derivatives of Allopregnane include the naturally occurring steroids Allopregnanolone, Allopregnanediol, Isopregnanolone, and 5α-Dihydroprogesterone. See also * 5β-Pregnane * Etiocholane * Gonane Gonane is a chemical compound with formula , whose molecule can be described as three molecules or entities of cyclohexane and one of cyclopentane, fused in a particular way. More specifically, the molecule can be described as that of cyclohe ... References * Endocrinology {{Steroid-stub ...
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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 women, 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, depression (mood), ...
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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 women, 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, depression (mood), ...
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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 (pregn-4-ene-3,20-dione) * Pregnanolone * Pregnanediol * Pregnanetriol * Pregna-4,20-dien-3,6-dione Pregnadienedione (PDD), or pregna-4,20-dien-3,6-dione, is a steroid and pherine, or synthetic pheromone. PDD has been found to activate the vomeronasal organ in men. Moreover, inhalation by men has been found to affect autonomic and central f ... * Hydroxyprogesterone References Pregnanes {{Chemistry index ...
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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 (pregn-4-ene-3,20-dione) * Pregnanolone * Pregnanediol * Pregnanetriol * Pregna-4,20-dien-3,6-dione Pregnadienedione (PDD), or pregna-4,20-dien-3,6-dione, is a steroid and pherine, or synthetic pheromone. PDD has been found to activate the vomeronasal organ in men. Moreover, inhalation by men has been found to affect autonomic and central f ... * Hydroxyprogesterone References Pregnanes {{Chemistry index ...
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Etiocholane
Etiocholane, also known as 5β-androstane or 5-epiandrostane, is an androstane (C19) steroid. It is the 5β-isomer of androstane. Etiocholanes include 5β-androstanedione, 5β-dihydrotestosterone, 3α,5β-androstanediol, 3β,5β-androstanediol, etiocholanolone, epietiocholanolone, and 3α,5β-androstanol. 17β-Ethyletiocholanes, or 5β-pregnanes, include 5β-dihydroprogesterone, pregnanolone, and epipregnanolone, as well as 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 ... and pregnanetriol. See also * C19H32 References {{DEFAULTSORT:Androstane, 5β- Etiocholanes ...
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Steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene. The steroid core structure is typically composed of seventeen carbon atoms, bonded in four " fused" rings: three six-member cyclohexane rings (rings A, B and C in the first illustration) and one five-member cyclopentane ring (the D ring). Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings. Sterols are forms of steroids with a hydroxy group at position three and a skeleton derived from cholestane. ''A ...
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Steroid Numbering
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene. The steroid core structure is typically composed of seventeen carbon atoms, bonded in four " fused" rings: three six-member cyclohexane rings (rings A, B and C in the first illustration) and one five-member cyclopentane ring (the D ring). Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings. Sterols are forms of steroids with a hydroxy group at position three and a skeleton derived from cholestane. ''Also ...
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