Desoxycorticosterone Pivalate
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Desoxycorticosterone Pivalate
Deoxycorticosterone pivalate (DOCP), also known as desoxycorticosterone trimethyl acetate (DOC-TMA or DCT) and sold under the brand names Zycortal, Percorten V, and Percorten M, is a mineralocorticoid medication and a mineralocorticoid ester. It is formulated as a microcrystalline aqueous suspension, is administered by intramuscular injection at regular intervals, and has a prolonged duration of action. The medication is the C21 pivalate (trimethylacetate) ester of 11-deoxycorticosterone 11-Deoxycorticosterone (DOC), or simply deoxycorticosterone, also known as 21-hydroxyprogesterone, as well as desoxycortone (INN), deoxycortone, and cortexone, is a steroid hormone produced by the adrenal gland that possesses mineralocorticoid ac .... See also * List of corticosteroid esters § Desoxycortone esters References Corticosteroid esters Diketones Mineralocorticoids Pivalate esters Pregnanes Prodrugs Progestogens Veterinary drugs {{Steroid-stub ...
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Intramuscular Injection
Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have larger and more numerous blood vessels than subcutaneous tissue, leading to faster absorption than subcutaneous or intradermal injections. Medication administered via intramuscular injection is not subject to the first-pass metabolism effect which affects oral medications. Common sites for intramuscular injections include the deltoid muscle of the upper arm and the gluteal muscle of the buttock. In infants, the vastus lateralis muscle of the thigh is commonly used. The injection site must be cleaned before administering the injection, and the injection is then administered in a fast, darting motion to decrease the discomfort to the individual. The volume to be injected in the muscle is usually limited to 2–5 milliliters, depending on in ...
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11-deoxycorticosterone
11-Deoxycorticosterone (DOC), or simply deoxycorticosterone, also known as 21-hydroxyprogesterone, as well as desoxycortone (INN), deoxycortone, and cortexone, is a steroid hormone produced by the adrenal gland that possesses mineralocorticoid activity and acts as a precursor to aldosterone. It is an active (Na+-retaining) mineralocorticoid. As its names indicate, can be understood as the 21- hydroxy-variant of progesterone or as the 11-deoxy-variant of corticosterone. ''DOCA'' is the abbreviation for the ester 11-deoxycorticosterone acetate. Biological activity DOC is a potent mineralocorticoid but is virtually devoid of glucocorticoid activity. However, 11β-hydroxylation of DOC produces corticosterone and confers glucocorticoid activity, along with 10-fold reduced mineralocorticoid activity. In addition to its mineralocorticoid activity, DOC has been found to possess one-third to one-tenth the potency of progesterone as a progestogen when administered systematically to r ...
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Prodrugs
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug is absorbed, distributed, metabolized, and excreted (ADME). Prodrugs are often designed to improve bioavailability when a drug itself is poorly absorbed from the gastrointestinal tract. A prodrug may be used to improve how selectively the drug interacts with cells or processes that are not its intended target. This reduces adverse or unintended effects of a drug, especially important in treatments like chemotherapy, which can have severe unintended and undesirable side effects. History Many herbal extracts historically used in medicine contain glycosides (sugar derivatives) of the active agent, which are hydrolyzed in the intestines to release the active and more bioavailable aglycone. For example, salicin is a β-D-glucopyranosid ...
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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-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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Pivalate Esters
Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (''t''-BuC(O)) is Piv and for pivalic acid (''t''-BuC(O)OH) is PivOH. Preparation Industrial route Pivalic acid is prepared by hydrocarboxylation of isobutene via the Koch reaction: :(CH3)2C=CH2 + CO + H2O → (CH3)3CCO2H Such reactions require an acid catalyst such as hydrogen fluoride. ''tert''-Butyl alcohol and isobutyl alcohol can also be used in place of isobutene. Globally, several million kilograms are produced annually. Pivalic acid is also economically recovered as a byproduct from the production of semisynthetic penicillins like ampicillin and amoxycillin. Laboratory methods It was originally prepared by the oxidation of pinacolone with chromic acid and by the hydrolysis of ''tert''-butyl cyanide. Convenient laboratory routes proceed via ''tert''-butyl chloride via ...
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Mineralocorticoids
Mineralocorticoids are a class of corticosteroids, which in turn are a class of steroid hormones. Mineralocorticoids are produced in the adrenal cortex and influence salt and water balances (electrolyte balance and fluid balance). The primary mineralocorticoid is aldosterone. Physiology The name mineralocorticoid derives from early observations that these hormones were involved in the retention of sodium, a mineral. The primary endogenous mineralocorticoid is aldosterone, although a number of other endogenous hormones (including progesterone and deoxycorticosterone) have mineralocorticoid function. Aldosterone acts on the kidneys to provide active reabsorption of sodium and an associated passive reabsorption of water, as well as the active secretion of potassium in the principal cells of the cortical collecting tubule and active secretion of protons via proton ATPases in the lumenal membrane of the intercalated cells of the collecting tubule. This in turn results in an increase ...
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Diketones
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical (dialdehydes, diketones, diesters, ''etc.'') or unsymmetrical (keto-esters, keto-acids, ''etc.''). 1,2-Dicarbonyls 1,2-Dialdehyde The only 1,2-dialdehyde is glyoxal, . Like many alkyldialdehydes, glyoxal is encountered almost exclusively as its hydrate and oligomers thereof. These derivatives often behave equivalently to the aldehydes since hydration is reversible. Glyoxal condenses re ...
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Corticosteroid Esters
This is a list of corticosteroid esters, including esters of steroidal glucocorticoids and mineralocorticoids. Esters of natural corticosteroids Desoxycortone esters * Desoxycortone acetate (deoxycortone acetate; desoxycorticosterone acetate) * Desoxycortone cypionate (deoxycortone cypionate; desoxycorticosterone cypionate) * Desoxycortone enanthate (deoxycortone enanthate; deoxycorticosterone enanthate) * Desoxycortone glucoside (deoxycortone glucoside; deoxycorticosterone glucoside) * Desoxycortone pivalate (deoxycortone pivalate; deoxycorticosterone pivalate) Hydrocortisone esters * Benzodrocortisone (hydrocortisone 17-benzoate) * Hydrocortamate (hydrocortisone 21-(diethylamino)acetate) * Hydrocortisone aceponate (hydrocortisone 21-acetate 17α-propionate) * Hydrocortisone acetate * Hydrocortisone bendazac * Hydrocortisone buteprate (hydrocortisone 17α-butyrate 21-propionate) * Hydrocortisone butyrate (hydrocortisone 17α-butyrate) * Hydrocortisone 21-butyrat ...
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List Of Corticosteroid Esters
This is a list of corticosteroid esters, including esters of steroidal glucocorticoids and mineralocorticoids. Esters of natural corticosteroids Desoxycortone esters * Desoxycortone acetate (deoxycortone acetate; desoxycorticosterone acetate) * Desoxycortone cypionate (deoxycortone cypionate; desoxycorticosterone cypionate) * Desoxycortone enanthate (deoxycortone enanthate; deoxycorticosterone enanthate) * Desoxycortone glucoside (deoxycortone glucoside; deoxycorticosterone glucoside) * Desoxycortone pivalate (deoxycortone pivalate; deoxycorticosterone pivalate) Hydrocortisone esters * Benzodrocortisone (hydrocortisone 17-benzoate) * Hydrocortamate (hydrocortisone 21-(diethylamino)acetate) * Hydrocortisone aceponate (hydrocortisone 21-acetate 17α-propionate) * Hydrocortisone acetate * Hydrocortisone bendazac * Hydrocortisone buteprate (hydrocortisone 17α-butyrate 21-propionate) * Hydrocortisone butyrate (hydrocortisone 17α-butyrate) * Hydrocortisone 21-butyrat ...
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Ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology Th ...
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Corticosteroid
Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are involved in a wide range of physiological processes, including stress response, immune response, and regulation of inflammation, carbohydrate metabolism, protein catabolism, blood electrolyte levels, and behavior. Some common naturally occurring steroid hormones are cortisol (), corticosterone (), cortisone () and aldosterone (). (Note that cortisone and aldosterone are isomers.) The main corticosteroids produced by the adrenal cortex are cortisol and aldosterone. Classes * Glucocorticoids such as cortisol affect carbohydrate, fat, and protein metabolism, and have anti-inflammatory, immunosuppressive, anti-proliferative, and vasoconstrictive effects. Anti-inflammatory effects are mediated by blocking the action of inflammatory medi ...
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Pivalate
Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (''t''-BuC(O)) is Piv and for pivalic acid (''t''-BuC(O)OH) is PivOH. Preparation Industrial route Pivalic acid is prepared by hydrocarboxylation of isobutene via the Koch reaction: :(CH3)2C=CH2 + CO + H2O → (CH3)3CCO2H Such reactions require an acid catalyst such as hydrogen fluoride. ''tert''-Butyl alcohol and isobutyl alcohol can also be used in place of isobutene. Globally, several million kilograms are produced annually. Pivalic acid is also economically recovered as a byproduct from the production of semisynthetic penicillins like ampicillin and amoxycillin. Laboratory methods It was originally prepared by the oxidation of pinacolone with chromic acid and by the hydrolysis of ''tert''-butyl cyanide. Convenient laboratory routes proceed via ''tert''-butyl chloride via ...
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