16-DPA
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16-DPA
16-Dehydropregnenolone acetate (16-DPA) is a chemical compound used as an intermediate or synthon in the production of many semisynthetic steroids. As 7-ACA is for cephalosporins and 6-APA is for penicillins, 16-DPA is for steroids. While it is not easy to synthesize, it is a convenient intermediate which can be made from other more available materials, and which can then be modified to produce the desired target compound. Upstream sources 16-DPA can be produced from a variety of steroidal sapogenins. Industrially useful sources are diosgenin in mexican yams and solasodine from certain nightshades. These two sapogenins can be used in a one-pot synthesis. Solanidine in potato greens, an alkaloid sapogenin, is also a key source material. Downstream products Compounds derived from 16-DPA include: * Corticosteroids (mainly of a C22 pregnane backbone): hydrocortisone*, betamethasone*, dexamethasone*, beclometasone*, fluticasone, and prednicarbate; * Progestogen (mainly of a C22 p ...
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Solanidine
Solanidine is a poisonous steroidal alkaloid chemical compound that occurs in plants of the family Solanaceae, such as potato and ''Solanum americanum''. Human ingestion of solanidine also occurs via the consumption of the glycoalkaloids, α-solanine and α-chaconine, present in potatoes.Kuiper-Goodman, T., Nawrot, P.S.Solanine and Chaconine IPCS Inchem The sugar portion of these glycoalkaloids hydrolyses in the body, leaving the solanidine portion. Solanidine occurs in the blood serum of normal healthy people who eat potato, and serum solanidine levels fall markedly once potato consumption ceases. Solanidine from food is also stored in the human body for prolonged periods of time, and it has been suggested that it could be released during times of metabolic stress with the potential for deleterious consequences. Solanidine is responsible for neuromuscular syndromes via cholinesterase inhibition.Everist, S.L., ''Poisonous Plants of Australia'', Angus and Robertson, 1974, . Uses ...
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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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Semisynthesis
Semisynthesis, or partial chemical synthesis, is a type of chemical synthesis that uses chemical compounds isolated from natural sources (such as microbial cell cultures or plant material) as the starting materials to produce novel compounds with distinct chemical and medicinal properties. The novel compounds generally have a high molecular weight or a complex molecular structure, more so than those produced by total synthesis from simple starting materials. Semisynthesis is a means of preparing many medicines more cheaply than by total synthesis since fewer chemical steps are necessary. Overview Drugs derived from natural sources are usually produced by isolation from the natural source or, as described here, by semisynthesis from such an isolated agent. From the viewpoint of chemical synthesis, living organisms are remarkable chemical factories that can easily produce structurally-complex chemical compounds by biosynthesis. In contrast, engineered chemical synthesis is necessar ...
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Solasodine
Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg. Literature survey reveals that solasodine has diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and various effects on central nervous system. Uses It is commercially used as a precursor for the production of complex steroidal compounds such as contraceptive pills, via a 16-DPA intermediate. See also * ''Solanum mauritianum ''Solanum mauritianum'' is a small tree or shrub native to South America, including Northern Argentina, Southern Brazil, Paraguay and Uruguay. Its common names include earleaf nightshade (or "ear-leaved nightshade"), woolly nightshade, flannel we ...'' References Steroidal alkaloids Plant toxins Steroi ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken and/or new bonds formed. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, using the s ...
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Prednicarbate
Prednicarbate is a relatively new topical corticosteroid drug. It is similar in potency to hydrocortisone. Corticosteroids have always been an important part of the pharmacological arsenal of dermatology Dermatology is the branch of medicine dealing with the skin.''Random House Webster's Unabridged Dictionary.'' Random House, Inc. 2001. Page 537. . It is a speciality with both medical and surgical aspects. A dermatologist is a specialist medical ...; however, their tendency to produce side-effects has caused the need to search for new preparations. It is nonhalogenated. References Corticosteroid esters Corticosteroids Propionate esters Carbonate esters {{dermatologic-drug-stub ...
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Dexamethasone
Dexamethasone is a glucocorticoid medication used to treat rheumatic problems, a number of skin diseases, severe allergies, asthma, chronic obstructive lung disease, croup, brain swelling, eye pain following eye surgery, superior vena cava syndrome (a complication of some forms of cancer), and along with antibiotics in tuberculosis. In adrenocortical insufficiency, it may be used in combination with a mineralocorticoid medication such as fludrocortisone. In preterm labor, it may be used to improve outcomes in the baby. It may be given by mouth, as an injection into a muscle, as an injection into a vein, as a topical cream or ointment for the skin or as a topical ophthalmic solution to the eye. The effects of dexamethasone are frequently seen within a day and last for about three days. The long-term use of dexamethasone may result in thrush, bone loss, cataracts, easy bruising, or muscle weakness. It is in pregnancy category C in the United States, meaning that it should ...
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Beclometasone
Beclomethasone, also known as beclomethasone dipropionate, and sold under the brand name Qvar among others, is a corticosteroid, steroid medication. It is available as an inhaler, cream, pills, and nasal spray. The inhaled form is used in the long-term management of asthma. The cream may be used for dermatitis and psoriasis. The pills have been used to treat ulcerative colitis. The nasal spray is used to treat allergic rhinitis and nasal polyps. Common side effects with the inhaled form include Respiratory tract infection, respiratory infections, headaches, and throat inflammation. Serious side effects include an increased risk of infection, cataracts, Cushing's syndrome, and anaphylaxis, severe allergic reactions. Long-term use of the pill form may cause adrenal insufficiency. The pills may also cause mood or personality changes. The inhaled form is generally regarded as safe in pregnancy. Beclometasone is mainly a glucocorticoid. Beclomethasone dipropionate was first patented ...
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Fluticasone
Fluticasone is a manufactured glucocorticoid used to treat nasal symptoms. Both the esters, fluticasone propionate (a brand name for which is Flovent) and fluticasone furoate, are also used as topical anti-inflammatories and inhaled corticosteroids, and are used much more commonly in comparison. It is on the World Health Organization's List of Essential Medicines. In 2020, it was the 23rd most commonly prescribed medication in the United States, with more than 24million prescriptions, although it is also sold over the counter. See also * Fluticasone furoate ** Fluticasone furoate/vilanterol * Fluticasone propionate ** Fluticasone/salmeterol Fluticasone/salmeterol, sold under the brand name Advair among others, is a fixed-dose combination medication containing fluticasone propionate and salmeterol. It is used in the management of asthma and chronic obstructive pulmonary disease (C ... References External links * Antiasthmatic drugs Diketones Diols Dr ...
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Pregnenolone
Pregnenolone (P5), or pregn-5-en-3β-ol-20-one, is an endogenous steroid and precursor/ metabolic intermediate in the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocorticoids. In addition, pregnenolone is biologically active in its own right, acting as a neurosteroid. In addition to its role as a natural hormone, pregnenolone has been used as a medication and supplement; for information on pregnenolone as a medication or supplement, see the pregnenolone (medication) article. Biological function Pregnenolone and its 3β-sulfate, pregnenolone sulfate, like DHEA, DHEA sulfate, and progesterone, belong to the group of neurosteroids that are found in high concentrations in certain areas of the brain, and are synthesized there. Neurosteroids affect synaptic functioning, are neuroprotective, and enhance myelinization. Pregnenolone and its sulfate ester may improve cognitive and memory function. In additi ...
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Progestogen
Progestogens, also sometimes written progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestogen in the body. The progestogens are named for their function in maintaining pregnancy (i.e., ''progestational''), although they are also present at other phases of the estrous and menstrual cycles. The progestogens are one of three types of sex hormones, the others being estrogens like estradiol and androgens/anabolic steroids like testosterone. In addition, they are one of the five major classes of steroid hormones, the others being the androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as the neurosteroids. All endogenous progestogens are characterized by their basic 21-carbon skeleton, called a pregnane skeleton (C21). In similar manner, the estrogens possess an estrane skeleton (C18), and androgens, an androstane skeleton (C19). ...
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Hydrocortisone
Hydrocortisone is the name for the hormone cortisol when supplied as a medication. 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, or by injection. Stopping treatment after long-term use should be done slowly. Side effects may include mood changes, increased risk of infection, and edema (swelling). With long-term use common side effects include osteoporosis, upset stomach, physical weakness, easy bruising, and candidiasis (yeast infections). While used, it is unclear if it is safe during pregnancy. Hydrocortisone is a glucocorticoid and works as an anti-inflammatory and by immune suppression. Hydrocortisone was patented in 1936 and approved for medical use in 1941. It is on the World Health Organization's List of Essential Medicines. It is available as a ...
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