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Encyclopedia > Teicoplanin
Teicoplanin
Systematic (IUPAC) name
 ?
Identifiers
CAS number 61036-62-2
ATC code J01XA02
PubChem  ?
Chemical data
Formula Variable
Mol. mass 1564.3 to 1907.7 g/mol
Pharmacokinetic data
Bioavailability 90% (given IM)
Protein binding 90% to 95%
Metabolism Nil
Half life 70 to 100 hours
Excretion Renal (97% unchanged)
Therapeutic considerations
Pregnancy cat.

B3(AU) Image File history File links Teicoplanin_core_and_major_components. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Intramuscular injection is the injection of a substance directly into a muscle. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The kidneys are organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ...

Legal status

POM(UK) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ...

Routes Intravenous, intramuscular

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 glycopeptide antiobiotic extracted from Actinoplanes teichomyceticus, with a similar spectrum of activity to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis. Teicoplanin is marketed by Aventis under the trade name Targocid®. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... Staphylococcus aureus - Antibiotics test plate. ... Prophylaxis refers to any medical or public health procedure whose purpose is to prevent, rather than treat or cure, disease. ... Gram-positive bacteria are those that are stained dark blue or violet by gram staining, in contrast to gram-negative bacteria, which are not affected by the stain. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... MRSA redirects here. ... Enterococci, traditionally viewed as Gram-positive commensal bacteria inhabiting the alimentary canals of humans and animals, are now acknowledged to be organisms capable of causing life-threatening infections in humans, especially in the nosocomial (hospital) environment. ... Crystal structure of a short peptide L-Lys-D-Ala-D-Ala (bacterial cell wall precursor, in green) bound to vancomycin (blue) through hydrogen bonds. ... Aventis was formed in 1999 when Rhône-Poulenc S.A. merged with Hoechst AG. The merged company was based in Strasbourg, France. ...


Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and Clostridium difficile-associated diarrhoea, with comparable efficacy to vancomycin.[1] Pseudomembranous colitis is an infection of the colon often, but not always, caused by the bacterium Clostridium difficile. ... Binomial name Hall & OToole, 1935 Clostridium difficile or CDF/cdf (commonly mistaken  , alternatively and correctly pronounced ) (also referred to as C. diff or C-diff) is a species of bacteria of the genus Clostridium which are gram-positive, anaerobic, spore-forming rods (bacillus). ...


Its strength is considered to be due to the length of the hydrocarbon chain.[2]


Chemistry

Teicoplanin is actually a mixture of several compounds, five major (named teicoplanin A2-1 through A2-5) and four minor (named teicoplanin RS-1 through RS-4).[3] All teicoplanins share a same glycopeptide core, termed teicoplanin A3-1 — a fused ring structure to which two carbohydrates (mannose and N-acetylglucosamine) are attached. The major and minor components also contain a third carbohydrate moiety — β-D-glucosamine — and differ only by the length and conformation of a side chain attached to it. Glycopeptide antibiotics are a class of antibiotic drugs. ... A macrocycle is, as defined by IUPAC, In the chemical literature, organic chemists may consider any molecule containing a ring of seven, fifteen, or any arbitrarily large number of atoms to be macrocyclic. ... Lactose is a disaccharide found in milk. ... D and L forms Haworth projection of mannose in its α-D-mannopyranose form. ... N-Acetylglucosamine (N-Acetyl-D-Glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. ... Look up moiety in Wiktionary, the free dictionary. ... Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. ... The term Side chain can have different meanings depending on the context: In chemistry and biochemistry a side chain is a part of a molecule attached to a core structure. ...


The structures of the teicoplanin core and the side chains which characterize the five major teicoplanin compounds are shown below.

Teicoplanin core (left, black) and side chains which characterize teicoplanins A2-1 through A2-5 (right). In blue: β-D-glucosamine.
Teicoplanin core (left, black) and side chains which characterize teicoplanins A2-1 through A2-5 (right). In blue: β-D-glucosamine.

Image File history File links Teicoplanin_core_and_major_components. ... Image File history File links Teicoplanin_core_and_major_components. ... Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. ...

References

  1. ^ de Lalla F, Nicolin R, Rinaldi E, Scarpellini P, Rigoli R, Manfrin V, Tramarin A (1992). "Prospective study of oral teicoplanin versus oral vancomycin for therapy of pseudomembranous colitis and Clostridium difficile-associated diarrhea.". Antimicrob Agents Chemother 36 (10): 2192-6. PMID 1444298. 
  2. ^ Gilpin M, Milner P (1997). Resisting changes -- Over the past 40 years the glycopeptide antibiotics have played a crucial role in treating bacterial infections. But how long can it continue ?. Royal Society of Chemistry. - includes picture of Teicoplanin's structure.
  3. ^ Bernareggi A, Borghi A, Borgonovi M, Cavenaghi L, Ferrari P, Vékey K, Zanol M, Zerilli L (1992). "Teicoplanin metabolism in humans". Antimicrob Agents Chemother 36 (8): 1744–9. PMID 1416858. 
v • d • e
Antibacterials for systemic use: others (J01X)
Glycopeptide Vancomycin - Teicoplanin
Polymyxins Colistin - Polymyxin B
Steroid antibacterials Fusidic acid
Imidazole derivatives Metronidazole - Tinidazole - Ornidazole
Nitrofuran derivatives Nitrofurantoin - Nifurtoinol
Other Fosfomycin - Xibornol - Clofoctol - Spectinomycin - Methenamine - Mandelic acid - Nitroxoline - Linezolid - Daptomycin - Hitachimycin

  Results from FactBites:
 
Indian Pediatrics - Editorial (1327 words)
Teicoplanin has bioavailability of 90-95% and its half-life is as long as 100 hours in patients with normal renal functions.
have shown that teicoplanin is as efficacious as vancomycin as empirical antibiotic regimen for febrile neutropenic patients with hematologic malignancies(16).
Teicoplanin is a glycopeptide having mechanism of action similar to that of vancomycin.
The WorldWide Intensivist: A brief review of Teicoplanin (1767 words)
Teicoplanin is a less toxic replacement for vancomycin in most situations where resistant organisms are encountered.
Teicoplanin is mainly used in moderate to severe infections with Gram-positive organisms.
Teicoplanin is actually a group of at least six bulky glycopeptides, all with very similar activities.
  More results at FactBites »


 

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