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 | | Amoxicillin | | Systematic (IUPAC) name | | 7-[2-amino-2-(4-hydroxyphenyl) -acetyl]amino-3,3-dimethyl-6-oxo -2-thia-5-azabicyclo[3.2.0]heptane -4-carboxylic acid | | Identifiers | | CAS number | 26787-78-0 | | ATC code | J01CA04 | | PubChem | 33613 | | DrugBank | APRD00248 | | Chemical data | | Formula | C16H19N3O5S | | Mol. mass | 365.4 g/mol | | Pharmacokinetic data | | Bioavailability | 95% oral | | Metabolism | less than 30% biotransformed in liver | | Half life | 61.3 minutes | | Excretion | renal | | Therapeutic considerations | | Pregnancy cat. | A(AU) B(US) Image File history File links Download high-resolution version (1100x567, 39 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Amoxicillin ...
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IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
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The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ...
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General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ...
General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Standard atomic weight 32. ...
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. ...
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Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ...
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. ...
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| | Routes | Oral, intravenous | Amoxicillin (INN) or amoxycillin (former BAN) is a moderate-spectrum β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, and so may be given with clavulanic acid to decrease its susceptibility (see below). It was developed by Beecham in 1972 and is currently marketed by GlaxoSmithKline (the inheritor company) under the original trade name Amoxil. 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. ...
An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ...
A British Approved Name (BAN) is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the British Pharmacopoeia (BP). ...
β-lactam antibiotics are a broad class of antibiotics which include penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ...
An infection is the detrimental colonization of a host organism by a foreign species. ...
A cluster of Escherichia coli bacteria magnified 10,000 times. ...
Beta-lactamase is an enzyme (EC 3. ...
Clavulanic acid is often combined with amoxicillin (to form co-amoxiclav) to treat certain infections caused by bacteria, including infections of the ears, lungs, sinus, skin, and urinary tract. ...
Beechams was the family business of Thomas Beecham, a chemist. ...
GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biological, and healthcare company. ...
Mode of action
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Main article: Beta-lactam antibiotic Amoxicillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. β-lactam antibiotics are a broad class of antibiotics which include penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ...
A cell wall is a fairly rigid layer surrounding a cell, located external to the cell membrane, that provides the cell with structural support, protection, and a filtering mechanism. ...
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. ...
Microbiology Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative organisms. Some examples of susceptible and resistant organisms, from the Amoxil® Approved Product Information (GSK, 2003), are listed below. 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. ...
Bacteria that are Gram-negative are not stained dark blue or violet by Gram staining, in contrast to Gram-positive bacteria. ...
Susceptible Gram-positive organisms Streptococcus spp., penicillin-susceptible Streptococcus pneumoniae, non β-lactamase-producing Staphylococcus spp., and Enterococcus faecalis. Streptococcus is a genus of spherical shaped Gram-positive bacteria, belonging to the phylum Firmicutes[1] and the lactic acid bacteria group. ...
Streptococcus is a genus of spherical shaped Gram-positive bacteria, belonging to the phylum Firmicutes[1] and the lactic acid bacteria group. ...
Beta-lactamase is an enzyme (EC 3. ...
Species S. aureus S. caprae S. epidermidis S. haemolyticus S. hominis S. lugdunensis S. saprophyticus S. warneri S. xylosus Staphylococcus (in Greek staphyle means bunch of grapes and coccos means granule) is a genus of Gram-positive bacteria. ...
Species E. faecalis etc. ...
Susceptible Gram-negative organisms Non-β-lactamase producing strains of the following bacteria: Haemophilus influenzae, Neisseria gonorrhoeae, Neisseria meningitidis, Escherichia coli, Proteus mirabilis and Salmonella spp. Beta-lactamase is an enzyme (EC 3. ...
Species H. ducreyi H. influenzae etc. ...
Neisseria is a genus of bacteria, included among the proteobacteria, a large group of gram-negative forms. ...
Neisseria is a genus of bacteria, included among the proteobacteria, a large group of gram-negative forms. ...
E. coli redirects here. ...
In biology, Proteus is a genus of Gram-negative Proteobacteria, which includes pathogens responsible for many human urinary tract infections. ...
Species Salmonella bongori Salmonella enterica Salmonella arizonae Salmonella enteritidis Salmonella typhi Salmonella typhimurium Salmonella is a genus of rod-shaped Gram-negative enterobacteria that causes typhoid fever, paratyphoid fever, and foodborne illness. ...
Resistant organisms Penicillinase-producing organisms, particularly penicillinase-producing Staphylococcus spp. Penicillinase-producing N. gonorrhoeae and H. influenzae are also resistant. Species S. aureus S. caprae S. epidermidis S. haemolyticus S. hominis S. lugdunensis S. saprophyticus S. warneri S. xylosus Staphylococcus (in Greek staphyle means bunch of grapes and coccos means granule) is a genus of Gram-positive bacteria. ...
All strains of Pseudomonas spp., Klebsiella spp., Enterobacter spp., indole-positive Proteus spp., Serratia marcescens, and Citrobacter spp. are resistant. Type species Pseudomonas aeruginosa Species group P. aeruginosa P. alcaligenes P. anguilliseptica P. argentinensis P. borbori P. citronellolis P. flavescens P. mendocina P. nitroreducens P. oleovorans P. pseudoalcaligenes P. resinovorans P. straminea group P. aurantiaca P. aureofaciens P. chlororaphis P. fragi P. lundensis P. taetrolens group P. antarctica P. azotoformans...
Klebsiella pneumoniae is a gram-negative rod-shaped bacteria, and clinically the most important member of the Klebsiella genus of Enterobacteriaceae. ...
Species etc. ...
Indole is an aromatic heterocyclic organic compound. ...
In biology, Proteus is a genus of Gram-negative Proteobacteria, which includes pathogens responsible for many human urinary tract infections. ...
Serratia marcescens is a Gram negative bacterium, a human pathogen of the family Enterobacteriaceae. ...
Species aka C. diversus Citrobacter is a genus of gram-negative bacteria in the family of the Enterobacteriaceae. ...
The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing. E. coli redirects here. ...
Doubling the routinely given concentration (in pediatrics) of amoxicillin has been shown to eradicate intermediately resistant Streptococcus pneumoniae in selected infections.[1]
Formulations Amoxicillin in trihydrate form is available as capsules, tablets, or syrup for oral use, and as the sodium salt for intravenous administration. It is one of the most common antibiotics issued to children. It has 3 ionizable groups.
Amoxicillin and clavulanic acid -
Main article: Co-amoxiclav Amoxicillin (in either trihydrate or sodium salt forms) may be combined with Clavulanic acid (as potassium clavulanate), a β-lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through β-lactamase production. This formulation is referred to as Co-amoxiclav (British Approved Name), but commonly by proprietary names such as Amoksiklav (×2 or SOLVO), Augmentin, Clamoxyl, Augclav, and Augmexx. Co-amoxiclav is the British Approved Name, in the British Pharmacopoeia, for the combination antibiotic containing amoxicillin and clavulanic acid. ...
Clavulanic acid is often combined with amoxicillin (to form co-amoxiclav) to treat certain infections caused by bacteria, including infections of the ears, lungs, sinus, skin, and urinary tract. ...
Potassium clavulanate or Clavulanate potassium is an enhanced property chemical based on the tertiary butylamine salt of clavulanic acid. ...
Bacteria that are Gram-negative are not stained dark blue or violet by Gram staining, in contrast to Gram-positive bacteria. ...
Co-amoxiclav is the British Approved Name, in the British Pharmacopoeia, for the combination antibiotic containing amoxicillin and clavulanic acid. ...
A British Approved Name (BAN) is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the British Pharmacopoeia (BP). ...
Side effects Side effects are as those for other beta-lactam antibiotics. Side effects include nausea, vomiting and easy fatigue. An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ...
β-lactam antibiotics are a broad class of antibiotics which include penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ...
For other uses, see Nausea (disambiguation). ...
The onset of an allergic reaction to Amoxicillin can be very sudden and intense - emergency medical attention must be sought as quickly as possible. The initial onset of such a reaction often starts with a change in mental state; skin rash with intense itching (often beginning in fingertips and around groin area and rapidly spreading) and sensations of fever, nausea and vomiting. Any other symptoms that seem even remotely suspicious must be taken very seriously.
Proprietary preparations The patent for amoxicillin has expired. Thus amoxicillin is marketed under many trade names including: Actimoxi, Amoksibos, Amoxiclav Sandoz, Amoxil, Amoksiklav, Amoxibiotic, Amoxicilina, Apo-Amoxi, Bactox, Betalaktam, Cilamox, Curam, Dedoxil, Dispermox, Duomox, Isimoxin, Klavox, Lamoxy, Moxypen, Moxyvit, Novamoxin, Ospamox, Panklav, Pamoxicillin, Polymox, Samthongcillin, Senox, Sinacilin, Trimox, Tolodina, Wymox, Zerrsox and Zimox.
See also Clavulanic acid is often combined with amoxicillin (to form co-amoxiclav) to treat certain infections caused by bacteria, including infections of the ears, lungs, sinus, skin, and urinary tract. ...
Co-amoxiclav is the British Approved Name, in the British Pharmacopoeia, for the combination antibiotic containing amoxicillin and clavulanic acid. ...
References GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biological, and healthcare company. ...
Otherwise known as the doctors prescribing Bible the British National Formulary (BNF) contains a wide spectrum of information on prescribing and pharmacology, among others indications, side effects and costs of the prescription of all medication drugs available on the National Health Service. ...
Footnotes The American Academy of Pediatrics (AAP) is an organization of pediatricians, physicians trained to deal with the medical care of infants, children, and adolescents. ...
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