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Amoxicillin
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| Systematic (IUPAC) name | |
| 7-[2-amino-2-(4-hydroxyphenyl) -acetyl]amino-3,3-dimethyl-6-oxo -2-thia-5-azabicyclo[3. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general 2. 0]heptane -4-carboxylic acid | |
| Identifiers | |
| CAS number | |
| ATC code | J01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C16H19N3O5S |
| Mol. mass | 365. CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 4 g/mol |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | 95% oral |
| Metabolism | less than 30% biotransformed in liver |
| Half life | 61. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The liver is a vital organ in the human body and is present in Vertebrates and some other animals The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity 3 minutes |
| Excretion | renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Oral, intravenous |
Amoxicillin (INN) or amoxycillin (BAN) is a moderate-spectrum, bacteriolytic, β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The kidneys are complicated organs that have numerous biological roles 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 For a topic outline on this subject see List of basic Australia topics. The United States of America —commonly referred to as the 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 The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom, the UK or Britain,is a Sovereign state located In Pharmacology and Toxicology, a route Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. An International Nonproprietary Name ( INN; also known as rINN, for recommended International Nonproprietary Name or pINN for proposed A British Approved Name ( BAN) is the official non-proprietary or generic name given to a Pharmaceutical Substance, as defined in the British Pharmacopoeia β-lactam antibiotics are a broad class of Antibiotics that include Penicillin derivatives Cephalosporins Monobactams Carbapenems The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have An infection is the detrimental Colonization of a host Organism by a foreign Species. A microorganism (also spelled micro organism or micro-organism and also called a microbe) is an Organism that is Microscopic (usually 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). Beta-lactamases are Enzymes ( produced by some bacteria and are responsible for their resistance to Beta-lactam antibiotics like Penicillins Clavulanic acid ( rINN) (klævjuːˌlænɨk ˈæsɨd is a Beta-lactamase inhibitor ( GlaxoSmithKline formerly Beecham) sometimes combined with It was developed by Beecham in 1972 and is currently marketed by GlaxoSmithKline (the inheritor company) under the original trade name Amoxil. Beecham was a British pharmaceutical company Following mergers in the late 20th century it is now part of GlaxoSmithKline. GlaxoSmithKline plc () is a United Kingdom -based pharmaceutical, biological and Healthcare Company.
Contents |
Mode of action
Amoxicillin acts by inhibiting the synthesis of bacterial cell walls. β-lactam antibiotics are a broad class of Antibiotics that include Penicillin derivatives Cephalosporins Monobactams Carbapenems It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. A cell wall is a tough flexible and sometimes fairly rigid layer surrounding a cell, located external to the Cell membrane, which provides the cell with structural Gram-positive bacteria are those that are stained dark blue or violet by Gram staining.
Microbiology
Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative organisms. Gram-positive bacteria are those that are stained dark blue or violet by Gram staining. Gram-negative bacteria are those Bacteria that do not retain Crystal violet dye in the Gram staining protocol Some examples of susceptible and resistant organisms, from the Amoxil Approved Product Information (GSK, 2003), are listed below.
Susceptible Gram-positive organisms
Streptococcus spp. Streptococcus is a Genus of spherical Gram-positive bacteria belonging to the phylum Firmicutes and the , penicillin-susceptible Streptococcus pneumoniae, non β-lactamase-producing Staphylococcus spp. Streptococcus is a Genus of spherical Gram-positive bacteria belonging to the phylum Firmicutes and the Beta-lactamases are Enzymes ( produced by some bacteria and are responsible for their resistance to Beta-lactam antibiotics like Penicillins Staphylococcus (in Greek σταφυλη staphyle means bunch of grapes and κοκκος coccos means granule is a genus of Gram-positive , and Enterococcus faecalis. Enterococcus is a Genus of Lactic acid bacteria of the phylum Firmicutes.
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-lactamases are Enzymes ( produced by some bacteria and are responsible for their resistance to Beta-lactam antibiotics like Penicillins Haemophilus is a Genus of Gram-negative, Pleomorphic, coccobacilli Bacteria belonging to the Pasteurellaceae Neisseria is a genus of Gram (- bacteria included among the Proteobacteria, a large group of Gram-negative forms Neisseria is a genus of Gram (- bacteria included among the Proteobacteria, a large group of Gram-negative forms Proteus is a genus of Gram-negative Proteobacteria, which includes Pathogens responsible for many Human Urinary tract infections Salmonella is a Genus of rod-shaped Gram-negative enterobacteria that causes Typhoid fever, Paratyphoid fever
Resistant organisms
Penicillinase-producing organisms, particularly penicillinase-producing Staphylococcus spp. Staphylococcus (in Greek σταφυλη staphyle means bunch of grapes and κοκκος coccos means granule is a genus of Gram-positive Penicillinase-producing N. gonorrhoeae and H. influenzae are also resistant.
All strains of Pseudomonas spp. Pseudomonas is a Genus of gamma Proteobacteria, belonging to the larger family of Pseudomonads Recently 16S rRNA sequence , Klebsiella spp. Klebsiella is a Genus of non-motile, Gram-negative, Oxidase-negative Bacteria with a prominent Polysaccharide , Enterobacter spp. Enterobacter is a genus of common Gram-negative, facultatively-anaerobic, rod-shaped Bacteria of the family Enterobacteriaceae , indole-positive Proteus spp. Indole is an Aromatic heterocyclic Organic compound. It has a bicyclic structure consisting of a six-membered Benzene ring fused to a five-membered Proteus is a genus of Gram-negative Proteobacteria, which includes Pathogens responsible for many Human Urinary tract infections , Serratia marcescens, and Citrobacter spp. Serratia is a Genus of Gram-negative, facultatively anaerobic, rod-shaped Bacteria of the Enterobacteriaceae Citrobacter is a Genus of Gram-negative coliform Bacteria in the Enterobacteriaceae family. are resistant.
The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing.
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, chewable and dispersable tablets plus syrup and paediatric suspension for oral use, and as the sodium salt for intravenous administration. It is one of the most common antibiotics issued to children, and the sweet-tasting liquid forms are helpful where the patient might find it difficult to take tablets or capsules. It has 3 ionizable groups.
Amoxicillin and clavulanic acid
To overcome the issue of β-lactamase production by resistant organisms, amoxicillin (in either trihydrate or sodium salt forms) may be combined with clavulanic acid, typically as the potassium salt. Co-amoxiclav is the British Approved Name, in the British Pharmacopoeia, for the combination antibiotic containing amoxicillin trihydrate a β-lactam Beta-lactamases are Enzymes ( produced by some bacteria and are responsible for their resistance to Beta-lactam antibiotics like Penicillins Clavulanic acid ( rINN) (klævjuːˌlænɨk ˈæsɨd is a Beta-lactamase inhibitor ( GlaxoSmithKline formerly Beecham) sometimes combined with Potassium (pəˈtæsiəm is a Chemical element. It has the symbol K (kalium from qalīy Atomic number 19 and Atomic mass 39 This combination has activity against a very broad array of Gram-positive, Gram-negative, and anaerobic organisms. Gram-positive bacteria are those that are stained dark blue or violet by Gram staining. Gram-negative bacteria are those Bacteria that do not retain Crystal violet dye in the Gram staining protocol An anaerobic organism is any Organism that does not require Oxygen for growth and may even die in its presence It is not active against MRSA, P. aeruginosa, or C. difficile. Pseudomonas aeruginosa is a Gram-negative, aerobic, rod-shaped Bacterium with unipolar motility. Clostridium difficile (pronounced /klɒsˈtrɪdiəm dɪˈfɪsɪli/ also known as CDF/cdf' or 'C It is available in oral preparations worldwide and also in the intravenous preparation in some countries. Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. The British Approved Name for this formulation is co-amoxiclav, but it is commonly referred to in practice by proprietary names such as Amoksiklav, Augmentin, Clamoxyl, Augclac, and Augmexx depending on country. A British Approved Name ( BAN) is the official non-proprietary or generic name given to a Pharmaceutical Substance, as defined in the British Pharmacopoeia Co-amoxiclav is the British Approved Name, in the British Pharmacopoeia, for the combination antibiotic containing amoxicillin trihydrate a β-lactam
Side effects
Side effects are as those for other beta-lactam antibiotics. An adverse drug reaction (abbreviated ADR) or adverse drug event (abbreviated ADE) is an expression that describes the unwanted negative consequences β-lactam antibiotics are a broad class of Antibiotics that include Penicillin derivatives Cephalosporins Monobactams Carbapenems Side effects include nausea, vomiting, and easy fatigue. Nausea ( Latin: Nausea, Greek:, " Sea-sickness " also called wamble) is the sensation of unease and discomfort Loose bowel movements (diarrhea) also may occur.
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.
Non-allergic amoxicillin rash
Somewhere between 3% to 10% of children taking amoxicillin (or ampicillin) show a late-developing (>72 hours after beginning medication and having never taken penicillin-like medication previously) non-itchy rash, sometimes referred to as the "amoxicillin rash. Ampicillin is a beta-lactam Antibiotic that has been used extensively to treat bacterial Infections since 1961 " The rash is described as maculopapular or morbilliform (measles-like), and starts on the trunk and can spread from there. Measles (rubeola is a Disease caused by a virus specifically a Paramyxovirus of the genus Morbillivirus. This rash is unlikely to be a true allergic reaction, and is not a contra-indication for future amoxicillin usage, nor should current regimen necessarily be stopped. However, as mentioned above, this common amoxicillin rash and a dangerous allergic reaction cannot easily be distinguished by inexperienced persons, and therefore a health professional should be consulted if a rash develops. (Pichichero, 2005; Schmitt 2005)
 Non-allergic amoxicillin rash 8 days after first dose, 24 hours after rash began. Diagnosed by pediactric resident at local university hospital. |
 8 hours after first photo. Individual spots have grown and begun to merge. |
 23 hours after first photo. Color apparently fading, much of rash has spread to confluence. |
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
References
- GlaxoSmithKline (February 2006). Clavulanic acid ( rINN) (klævjuːˌlænɨk ˈæsɨd is a Beta-lactamase inhibitor ( GlaxoSmithKline formerly Beecham) sometimes combined with Co-amoxiclav is the British Approved Name, in the British Pharmacopoeia, for the combination antibiotic containing amoxicillin trihydrate a β-lactam GlaxoSmithKline plc () is a United Kingdom -based pharmaceutical, biological and Healthcare Company. Amoxil - Prescribing information (PDF).
- Neal, MJ (2002). Medical Pharmacology at a Glance (4 ed. ). Oxford: Blackwell Science. ISBN 0-632-05244-9
- Pichichero, Michael E. "A Review of Evidence Supporting the American Academy of Pediatrics Recommendation for Prescribing Cephalosporin Antibiotics for Penicillin-Allergic Patients. " Pediatrics, 2005, 115 1048-1057. PMID 15805383
- Schmitt, Barton D. "Your Child's Health: The Parents' One-Stop Reference Guide to: Symptoms, Emergencies, Common Illnesses, Behavior Problems, and Healthy Development" 2nd Ed. , Bantam (2005). ISBN 0553383698
- British National Formulary 45 March 2003
- Amoxicillin.com - Amoxicillin information
Footnotes
- ^ (2003) 2003 Red Book: Report of the Committee on Infectious Diseases. The British National Formulary (BNF contains a wide spectrum of information on prescribing and Pharmacology, among others indications Side effects and Elk Grove Village, Illinois: American Academy of Pediatrics. The American Academy of Pediatrics ( AAP) is an organization of Pediatricians physicians trained to deal with the medical care of infants children and adolescents ISBN 11-58110-095-7.
External links
- University of Michigan Mott's Children's Hospital article about "amoxicillin rash." (Very similar to Schmitt 2005 content)
Dictionary
amoxicillin
-noun
- (pharmacology) A moderate-spectrum, bacteriolytic, β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms, with formula C16H19N3O5S.
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