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IUPAC name 14-Hydroxy-3β-[(3-O-methyl-β-D-quinovopyranosyl)-(1→4)-(3-O-methyl-2-deoxy-β-D-ribo-hexopyranosyl)-(1→4)-3-O-methyl-2-deoxy-β-D-ribo-hexopyranosyloxy]-20-oxo-14β-pregn-5-en-12β-yl (2E)-2-methylbut-2-enoate | |
Systematic IUPAC name (11S,13aS,13bR,17S,19aR,19bS,111R,111aS,32R,34S,35R,36R,52S,54S,55R,56R,72S,73R,74S,75R,76R)-11-Acetyl-13a,73,75-trihydroxy-34,54,74-trimethoxy-19a,111a,36,56,76-pentamethyl-12,13,13a,14b,14,16,17,18,19,19a,19b,110,111,111a-tetradecahydro-11H-2,4,6-trioxa-3,5(2,5),7(2)-tris(oxana)-1(7)-cyclopenta[a]phenanthrenaheptaphan-111-yl (2E)-2-methylbut-2-enoate | |
Other names P57 P57AS3 | |
Identifiers | |
3D model (JSmol) | |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C47H74O15 | |
Molar mass | 879.094 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
P57 is an oxypregnane steroidal glycoside isolated from the African cactiform Hoodia gordonii . P57 is hypothesized to be the chemical constituent from this plant mainly responsible for the putative appetite suppressant activity of Hoodia extracts. [1] [2] [3]
In a study on rats at Brown Medical School, intracerebroventricular injections of the purified P57 demonstrated that the compound has a likely central nervous system (CNS) mechanism of action like that of neuroactive steroids. [4] The studies demonstrated that the compound increases the content of ATP by 50-150% in hypothalamic neurons. In addition, third ventricle administration of P57 reduced subsequent 24-hour food intake by 40-60%.
Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.
Bioprospecting is the exploration of natural sources for small molecules, macromolecules and biochemical and genetic information that could be developed into commercially valuable products for the agricultural, aquaculture, bioremediation, cosmetics, nanotechnology, or pharmaceutical industries. In the pharmaceutical industry, for example, almost one third of all small-molecule drugs approved by the U.S. Food and Drug Administration (FDA) between 1981 and 2014 were either natural products or compounds derived from natural products.
Benzphetamine is a substituted amphetamine used short-term along with a doctor-approved, reduced-calorie diet, exercise, and behavioral program for weight loss. It is prescribed for obesity to people who have been unable to lose weight through exercise and dieting alone. It is a prodrug to dextroamphetamine and dextromethamphetamine.
Saponins, also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort, a flowering plant, the soapbark tree and soybeans. They are used in soaps, medicines, fire extinguishers, speciously as dietary supplements, for synthesis of steroids, and in carbonated beverages. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin and quillaia, a bark extract used in beverages.
An anorectic or anorexic is a drug which reduces appetite, resulting in lower food consumption, leading to weight loss. By contrast, an appetite stimulant is referred to as orexigenic.
Hoodia is a genus of flowering plants in the family Apocynaceae, under the subfamily Asclepiadoideae, native to Southern Africa.
Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.
Neurosteroids, also known as neuroactive steroids, are endogenous or exogenous steroids that rapidly alter neuronal excitability through interaction with ligand-gated ion channels and other cell surface receptors. The term neurosteroid was coined by the French physiologist Étienne-Émile Baulieu and refers to steroids synthesized in the brain. The term, neuroactive steroid refers to steroids that can be synthesized in the brain, or are synthesized by an endocrine gland, that then reach the brain through the bloodstream and have effects on brain function. The term neuroactive steroids was first coined in 1992 by Steven Paul and Robert Purdy. In addition to their actions on neuronal membrane receptors, some of these steroids may also exert effects on gene expression via nuclear steroid hormone receptors. Neurosteroids have a wide range of potential clinical applications from sedation to treatment of epilepsy and traumatic brain injury. Ganaxolone, a synthetic analog of the endogenous neurosteroid allopregnanolone, is under investigation for the treatment of epilepsy.
Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides. These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically, they can cause an atrioventricular block, bradycardia, ventricular tachycardia, and possibly lethal cardiac arrest.
Mazindol is a stimulant drug which is used as an appetite suppressant. It was developed by Sandoz-Wander in the 1960s.
Hoodia gordonii, also known as Bushman’s hat, is a leafless spiny succulent plant supposed to have therapeutic properties in folk medicine. It grows naturally in Botswana, South Africa and Namibia. The species became internationally known and threatened by collectors, after a marketing campaign falsely claimed that it was an appetite suppressant for weight loss. The flowers smell like rotten meat and are pollinated mainly by flies. The indigenous San people of the Namib desert call this plant ǁhoba.
Ginsenosides or panaxosides are a class of natural product steroid glycosides and triterpene saponins. Compounds in this family are found almost exclusively in the plant genus Panax (ginseng), which has a long history of use in traditional medicine that has led to the study of pharmacological effects of ginseng compounds. As a class, ginsenosides exhibit a large variety of subtle and difficult-to-characterize biological effects when studied in isolation.
Protodioscin is a steroidal saponin compound found in a number of plant species, most notably in the Tribulus, TrigonellaDioscorea and Trillium families. It is best known as the putative active component of the herbal aphrodisiac plant Tribulus terrestris.
Tiflorex (TFX), formerly known as flutiorex, is a stimulant amphetamine that was under development as an appetite suppressant in the 1970s, but appears to have been abandoned. It is structurally related to fenfluramine and 4-MTA.
An orexigenic, or appetite stimulant, is a drug, hormone, or compound that increases appetite and may induce hyperphagia. This can be a medication or a naturally occurring neuropeptide hormone, such as ghrelin, orexin or neuropeptide Y, which increases hunger and therefore enhances food consumption. Usually appetite enhancement is considered an undesirable side effect of certain drugs as it leads to unwanted weight gain, but sometimes it can be beneficial and a drug may be prescribed solely for this purpose, especially when the patient is suffering from severe appetite loss or muscle wasting due to cystic fibrosis, anorexia, old age, cancer or AIDS. There are several widely used drugs which can cause a boost in appetite, including tricyclic antidepressants (TCAs), tetracyclic antidepressants, natural or synthetic cannabinoids, first-generation antihistamines, most antipsychotics and many steroid hormones. In the United States, no hormone or drug has currently been approved by the FDA specifically as an orexigenic, with the exception of Dronabinol, which received approval for HIV/AIDS-induced anorexia only.
Levofenfluramine (INN), or (−)-3-trifluoromethyl-N-ethylamphetamine, also known as (−)-fenfluramine or (R)-fenfluramine, is a drug of the amphetamine family that, itself (i.e., in enantiopure form), was never marketed. It is the levorotatory enantiomer of fenfluramine, the racemic form of the compound, whereas the dextrorotatory enantiomer is dexfenfluramine. Both fenfluramine and dexfenfluramine are anorectic agents that have been used clinically in the treatment of obesity (and hence, levofenfluramine has been as well since it is a component of fenfluramine). However, they have since been discontinued due to reports of causing cardiovascular conditions such as valvular heart disease and pulmonary hypertension, adverse effects that are likely to be caused by excessive stimulation of 5-HT2B receptors expressed on heart valves.
Sarcococca saligna, the sweet box or Christmas box, is a species of flowering plant in the family Buxaceae. This shrub is native to northern Pakistan. Its common name in Pakistan is sheha.
5β-Dihydroprogesterone is an endogenous neurosteroid and an intermediate in the biosynthesis of pregnanolone and epipregnanolone from progesterone. It is synthesized from progesterone by the enzyme 5β-reductase.
Atractyloside (ATR) is a natural, toxic glycoside present in numerous plant species worldwide in the daisy family including Atractylis gummifera and Callilepis laureola, and it's used for a variety of therapeutic, religious, and toxic purposes. Exposure to ATR via ingestion or physical contact is toxic and can be fatal for both humans and animals, especially by kidney and liver failure. ATR acts as an effective ADP/ATP translocase inhibitor which eventually halts ADP and ATP exchange and the cell dies due to lack of energy. Historically, atractyloside poisoning has been challenging to verify and quantify toxicologically, though recent literature has described such methods within acceptable standards of forensic science.
Desmethylsibutramine is an active metabolite of the anorectic drug sibutramine. It is a more potent monoamine reuptake inhibitor than sibutramine and has been sold as an ingredient in weight loss products sold as dietary supplements, along with related compounds such as the N-ethyl and 3,4-dichloro derivatives.