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Teicoplanin P450 Oxidations
Teicoplanin is an antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant ''Staphylococcus aureus'' and ''Enterococcus faecalis''. It is a semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis. Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticocin marketed by Cipla(India). Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and ''Clostridium difficile''-associated diarrhoea, with comparable efficacy with vancomycin. Its strength is considered to be due to the length of the hydrocarbon chain. Teicoplanin is produced by so-called "rare" actinobacterium ''Actinoplanes teichomyceticus'' ATCC 31121, belonging to the ''Micromonosporaceae'' family. Biosynthetic pathway leading to teicoplanin, as well as t ...
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Intravenous Therapy
Intravenous therapy (abbreviated as IV therapy) is a medical technique that administers fluids, medications and nutrients directly into a person's vein. The intravenous route of administration is commonly used for rehydration or to provide nutrients for those who cannot, or will not—due to reduced mental states or otherwise—consume food or water by mouth. It may also be used to administer medications or other medical therapy such as blood products or electrolytes to correct electrolyte imbalances. Attempts at providing intravenous therapy have been recorded as early as the 1400s, but the practice did not become widespread until the 1900s after the development of techniques for safe, effective use. The intravenous route is the fastest way to deliver medications and fluid replacement throughout the body as they are introduced directly into the circulatory system and thus quickly distributed. For this reason, the intravenous route of administration is also used for the consump ...
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Carbohydrate
In organic chemistry, a carbohydrate () is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus with the empirical formula (where ''m'' may or may not be different from ''n''), which does not mean the H has covalent bonds with O (for example with , H has a covalent bond with C but not with O). However, not all carbohydrates conform to this precise stoichiometric definition (e.g., uronic acids, deoxy-sugars such as fucose), nor are all chemicals that do conform to this definition automatically classified as carbohydrates (e.g. formaldehyde and acetic acid). The term is most common in biochemistry, where it is a synonym of saccharide (), a group that includes sugars, starch, and cellulose. The saccharides are divided into four chemical groups: monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides and disaccharides, the smallest (lower molecular wei ...
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Glycopeptide Antibiotics
Glycopeptide antibiotics are a class of drugs of microbial origin that are composed of glycosylated cyclic or polycyclic nonribosomal peptides. Significant glycopeptide antibiotics include the anti-infective antibiotics vancomycin, teicoplanin, telavancin, ramoplanin and decaplanin, corbomycin, complestatin and the antitumor antibiotic bleomycin. Vancomycin is used if infection with methicillin-resistant Staphylococcus aureus, methicillin-resistant ''Staphylococcus aureus'' (MRSA) is suspected. Mechanism and classification Some members of this class of drugs inhibit the synthesis of cell walls in susceptible microbes by inhibiting peptidoglycan synthesis. The core class (including vancomycin) binds to acyl-D-alanyl-D-alanine in lipid II, preventing the addition of new units to the peptidoglycan. Of this core class, one may distinguish multiple generations: the first generation includes vancomycin and teicoplanin, while the semisynthetic second generation includes lipoglycopept ...
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Teicoplanin P450 Oxidations
Teicoplanin is an antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant ''Staphylococcus aureus'' and ''Enterococcus faecalis''. It is a semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis. Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticocin marketed by Cipla(India). Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and ''Clostridium difficile''-associated diarrhoea, with comparable efficacy with vancomycin. Its strength is considered to be due to the length of the hydrocarbon chain. Teicoplanin is produced by so-called "rare" actinobacterium ''Actinoplanes teichomyceticus'' ATCC 31121, belonging to the ''Micromonosporaceae'' family. Biosynthetic pathway leading to teicoplanin, as well as t ...
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Atropisomer
Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to allow for isolation of individual conformers. They occur naturally and are important in pharmaceutical design. When the substituents are achiral, these conformers are enantiomers (''atropoenantiomers''), showing axial chirality; otherwise they are diastereomers (''atropodiastereomers''). Etymology and history The word ''atropisomer'' ( el, άτροπος, , meaning "without turn") was coined in application to a theoretical concept by German biochemist Richard Kuhn for Karl Freudenberg's seminal ''Stereochemie'' volume in 1933. Atropisomerism was first experimentally detected in a tetra substituted biphenyl, a diacid, by George Christie and James Kenner in 1922. Michinori Ōki further refined the definition of atropisomers taking into account the temperature-dependence asso ...
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3,5-dihydroxyphenylglycine
(''S'')-3,5-Dihydroxyphenylglycine or DHPG is a potent agonist of group I metabotropic glutamate receptors (mGluRs) mGluR1 and mGluR5. DHPG was the first agonist shown to be selective for group I mGluRs. Agonist activity is found in only the (''S'')- isomer, and (''S'')-DHPG may be a partial agonist of group I mGluRs. (''S'')-DHPG has been investigated for therapeutic effects in the treatment of neuronal injury (such as those associated with ischemia or hypoxia), cognitive enhancement, and Alzheimer's disease. 3,5-Dihydroxyphenylglycine can be isolated from the latex of ''Euphorbia helioscopia''. DHGP is also found in vancomycin and related glycopeptides. Although the (S) stereoisomer is synthesized by the DpgA-D enzymes, it is the (R) stereoisomer that is used in vancomycin and other related compounds. DHPG is enzymatically derived from the polyketide Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone ...
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4-Hydroxyphenylglycine
4-Hydroxyphenylglycine (HPG) is a non-proteogenic amino acid found in vancomycin and related glycopeptides. HPG is synthesized from the shikimic acid pathway and requires four enzymes to synthesize: Both L- and D-HPG are used in the vancomycin class of antibiotics. Tyrosine, a similar amino acid, differs by a methylene group (CH2) between the aromatic ring and the alpha carbon. Biosynthesis : HPG is synthesized from prephenate, an intermediate in the shikimic acid pathway and also a precursor to tyrosine. Prephenate is aromatized by prephenate dehydrogenase (Pdh) using NAD+ as a cofactor to produce 4-hydroxyphenylpyruvate. 4-Hydroxyphenylpyruvate is then oxidized by 4-hydroxymandelate synthase (4HmaS) using oxygen to form 4-hydroxymandelate and hydrogen peroxide. 4HmaS is a non-heme iron-dependent dioxygenase. The reaction mechanism of this unique oxidation was proposed by Choroba ''et al'' in 2000 : 4-Hydroxymandelate is subsequently oxidized by hydroxymandelate oxidase (Hm ...
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Actinoplanes Teichomyceticus
''Actinoplanes'' is a genus in the family Micromonosporaceae. They have aerial mycelia and spherical, motile spores. ''Actinoplanes'' species produce the pharmaceutically important compounds valienamine (a precursor to the antidiabetic drug acarbose and to the antibiotic validamycin), teicoplanin, and ramoplanin Ramoplanin (INN) is a glycolipodepsipeptide antibiotic drug derived from strain ATCC 33076 of ''Actinoplanes''. It is effective against Gram-positive bacteria. Mechanism It exerts its bacteriocidal effect by inhibiting cell wall biosynthesi .... Species ''Actinoplanes'' comprises the following species: * '' A. abujensis'' Sazak et al. 2012 * "'' A. arizonaensis''" Karwowski et al. 1988 * '' A. atraurantiacus'' Zhang et al. 2012 * '' A. auranticolor'' (Couch 1963) Stackebrandt and Kroppenstedt 1988 * "'' A. aureus''" Song et al. 2021 * '' A. bogorensis'' corrig. Nurkanto et al. 2016 * '' A. brasiliensis'' Thiemann et al. 1969 (Approved Lists 1980) * '' A. camp ...
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Teicoplanin Core And Major Components
Teicoplanin is an antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacterium, bacteria, including methicillin-resistant Staphylococcus aureus, methicillin-resistant ''Staphylococcus aureus'' and ''Enterococcus faecalis''. It is a semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis. Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticocin marketed by Cipla(India). Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and ''Clostridium difficile colitis, Clostridium difficile''-associated diarrhoea, with comparable efficacy with vancomycin. Its strength is considered to be due to the length of the hydrocarbon chain. Teicoplanin is produced by so-called "rare" actinobacterium ''Actinoplanes teichomyceticus'' ATCC 31121, belonging to the '' ...
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Side Chain
In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called the "main chain" or backbone. The side chain is a hydrocarbon branching element of a molecule that is attached to a larger hydrocarbon backbone. It is one factor in determining a molecule's properties and reactivity. A side chain is also known as a pendant chain, but a pendant group (side group) has a different definition. Conventions The placeholder R is often used as a generic placeholder for alkyl (saturated hydrocarbon) group side chains in chemical structure diagrams. To indicate other non-carbon groups in structure diagrams, X, Y, or Z are often used. History The ''R'' symbol was introduced by 19th-century French chemist Charles Frédéric Gerhardt, who advocated its adoption on the grounds that it would be widely recognizable and intelligible given its correspondence in multiple European languages to the initial letter of "root" or "residue": ...
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Glucosamine
Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country. Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug. Dietary supplement Oral glucosamine is a dietary supplement and is not a prescription drug. Glucosamine is marketed as a supplement to support the structure and function of joints, and the marketing is targeted to people with osteoarthritis. Commonly sold forms of glucosamine are glucosamine sulfate, glucosamine chondroitin, glucosamine hydrochloride, and ''N''-acetylglucos ...
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Moiety (chemistry)
In organic chemistry, a moiety ( ) is a part of a molecule that is given a name because it is identified as a part of other molecules as well. Typically, the term is used to describe the larger and characteristic parts of organic molecules, and it should not be used to describe or name smaller functional groups of atoms that chemically react in similar ways in most molecules that contain them. Occasionally, a moiety may contain smaller moieties and functional groups. A moiety that acts as a branch extending from the backbone of a hydrocarbon molecule is called a substituent or side chain, which typically can be removed from the molecule and substituted with others. Active moiety In pharmacology, an active moiety is the part of a molecule or ion – excluding appended inactive portions – that is responsible for the physiological or pharmacological action of a drug substance. Inactive appended portions of the drug substance may include either the alcohol or acid moiety of ...
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