AmoxicillinFrom Wikipedia, the free encyclopediaAmoxicillin

Systematic (IUPAC) name

(2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-24-carboxylic acid

Clinical data

Trade namesActimoxi, Alphamox, Amocla, Tycil, Amoxil, and Trimox, among others

AHFS/Drugs.commonograph

MedlinePlusa685001

Pregnancycategory AU:A US:B(No risk in non-human studies)

Legal status UK:Prescription-only(POM) US:-only

Routes ofadministrationOral,intravenous

Pharmacokinetic data

Bioavailability95% oral

Metabolismless than 30% biotransformed inliver

Half-life61.3 minutes

Excretionrenal

Identifiers

CAS Registry Number26787-78-0

ATC codeJ01CA04QG51AA03

PubChemCID:33613

DrugBankDB01060

ChemSpider31006

UNII9EM05410Q9

KEGGD07452

ChEBICHEBI:2676

ChEMBLCHEMBL1082

Chemical data

FormulaC16H19N3O5S

Molecular mass365.4 g/mol

SMILES[show]

InChI[show]

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Amoxicillin BPAmoxicillin(INN,BAN), oramoxycillin(AAN), and abbreviatedamox, is anantibioticuseful for the treatment of a number ofbacterialinfections.It is a moderate-spectrum, bacteriolytic,-Lactam antibioticin theaminopenicillinfamily used to treat susceptibleGram-positiveandGram-negativebacteria. It is usually the drug of choice within the class because it is better-absorbed, following oral administration, than other -lactam antibiotics. Amoxicillin is susceptible to degradation by-lactamase-producing bacteria, which are resistant to a narrow spectrum of -lactam antibiotics, such aspenicillin. For this reason, it is often combined withclavulanic acid, a -lactamase inhibitor. This drug combination is commonly calledco-amoxiclav. Combining the drugs increases effectiveness by reducing susceptibility to -lactamase resistance.[1]Side effects include an increased risk ofyeast infectionsand, when used in combination withclavulanic acid,diarrhea.[2]Amoxicillin is one of the most commonantibioticsprescribed for children. The drug first became available in1972. It is on theWorld Health Organization's List of Essential Medicines, a list of the most important medications needed in a basichealth system.[3]Contents[hide] 1Medical uses 2Adverse effects 2.1Nonallergic amoxicillin rash 2.2Interaction 3Mechanism of actions 4Spectrum of microorganism susceptibility and resistance 5History 6Formulations 6.1Modes of delivery 6.2Brand names 7References 8Further reading 9External linksMedical uses[edit]Amoxicillin is used in the treatment of a number of infections, includingacute otitis media,streptococcal pharyngitis,pneumonia,skin infections,urinary tract infections,Salmonellainfections,Lyme disease, andchlamydiainfections.[4]It is also used to preventbacterial endocarditisin high-risk people having dental work done, to preventStreptococcus pneumoniaeand other encapsulated bacterial infections in those withoutspleens, such as people withsickle-cell disease, and for both the prevention and the treatment ofanthrax.[4]The United Kingdom recommends against its use for infectious endocarditis prophylaxis.[5]These recommendations have not appeared to have changed the rates of infection for infectious endocarditis.[6]Amoxicillin and amoxicillin-clavulanate have been recommended by guidelines as the drug of choice for bacterialsinusitis, but most sinusitis is caused by viruses, for which amoxicillin and amoxicillin-clavulanate are ineffective,[7]and the small benefit gained by Amoxicillin may be overridden by the adverse effects.[8]Amoxicillin is occasionally used for the treatment of skin infections, such asacne vulgaris.[9]It is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such asdoxycyclineandminocycline.[10]Adverse effects[edit]Side effectsare similar to those for other-lactam antibiotics, includingnausea, vomiting, rashes, and antibiotic-associatedcolitis. Loose bowel movements (diarrhea) may also occur. Rarer side effects include mental changes, lightheadedness, insomnia, confusion, anxiety, sensitivity to lights and sounds, and unclear thinking. Immediate medical care is required upon the first signs of these side effects.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 phase 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. However, more mild allergy symptoms, such as a rash, can occur at any time during treatment, even up to a week after treatment has ceased. For some people allergic to amoxicillin, the side effects can be fatal due toanaphylaxis.Use of the amoxicillin/clavulanic acid combination for more than one week has caused mildhepatitisin some patients. Young children having ingested acute overdoses of amoxicillin manifestedlethargy, vomiting, andrenal dysfunction.[11][12]Nonallergic amoxicillin rash[edit]Between 3 and 10% of children taking amoxicillin (orampicillin) show a late-developing (>72 hours after beginning medication and having never taken penicillin-like medication previously) rash, which is sometimes referred to as the "amoxicillin rash". The rash can also occur in adults.The rash is described asmaculopapularor morbilliform (measles-like; therefore, in medical literature, it is called "amoxicillin-induced morbilliform rash".[13]) It starts on the trunk and can spread from there. This rash is unlikely to be a true allergic reaction, and is not a contraindication for future amoxicillin usage, nor should the current regimen necessarily be stopped. However, this common amoxicillin rash and a dangerous allergic reaction cannot easily be distinguished by inexperienced persons, so a healthcare professional is often required to distinguish between the two.[14][15]A nonallergic amoxicillin rash may also be an indicator ofinfectious mononucleosis. Some studies indicate about 80-90% of patients with acuteEpstein Barr virusinfection treated with amoxicillin or ampicillin develop such a rash.[16] Nonallergic amoxicillin rash eight days after first dose: This photo was taken 24 hours after the rash began. Eight hours after the first photo, individual spots have grown and begun to merge. At 23 hours after the first photo, the color appears to be fading, and much of rash has spread to confluence.Interaction[edit]Amoxicillin may interact with these drugs: Anticoagulants (e.g.,warfarin,dabigatran)[17] Allopurinol(gout treatment) Certain antibiotics Cancer treatment (methotrexate) Uricosuric drugs Typhoid vaccineMechanism of actions[edit]Main article:Beta-lactam antibioticThis drug acts by inhibiting the synthesis of bacterialcell walls. It inhibitscross-linkagebetween the linear peptidoglycan polymer chains that make up a major component of thecell wallsof bothGram-positiveandGram-negative bacteria.It has twoionizablegroups in the physiological range (the amino group in alpha-position to the amide carbonyl group and the carboxyl group).Spectrum of microorganism susceptibility and resistance[edit]In general,Streptococcus, Bacillus subtilis, Enterococcus, Haemophilus, Helicobacter,andMoraxellaare susceptible to amoxicillin, whereasCitrobacter, KlebsiellaandPseudomonas aeruginosaare resistant to it.[18]SomeE. coliand most clinical isolates ofStaphylococcus aureushave developed resistance to amoxicillin to varying degrees.History[edit]See also:Timeline of antibioticsAmoxicillin was one of severalsemisyntheticderivatives of 6-aminopenicillanic acid (6-APA) developed atBeecham, Englandin the 1960s. It became available in 1972, and was the secondaminopenicillinto reach the market (afterampicillinin 1961).[19][20][21]Co-amoxiclavbecame available in 1981.[20]Formulations[edit]Modes of delivery[edit]Pharmaceutical manufacturers make amoxicillin intrihydrateform, for oral use available as capsules, chewable and dispersibletablets, syrup andpediatricsuspensionfor oral use, and as the sodium salt forintravenousadministration. Amoxicillin is most commonly taken orally. The liquid forms are helpful where the patient might find it difficult to take tablets or capsules. Intravenous form is not sold in USAResearch with mice indicated successful delivery usingintraperitoneallyinjected amoxicillin-bearingmicroparticles.[22]Brand names[edit]

Novamoxin prescription drug500mgAmoxicillin trihydrateAmoxicillin is one of the semisynthetic penicillins discovered byBeechamscientists. The patent for amoxicillin has expired, thus amoxicillin and co-amoxiclav preparations are marketed under many trade names and/or have several synonyms across the world, such as: Actimoxi[23] Alphamox Amimox Amocla AMK Amoksiklav Amorion Amoxibactin (animal use) Amoxibos Amoxiclav Amoxidal Amoxil Amoxin[24] Amoxibiotic[25] Amoxicilina Amoxidal Amoxoral (animal use) Apo-Amoxy Arsogil[26] Augmentin Bactox Bioxidona[27] Cilamox Clamoxyl Clavamox Clonamox Curam Dedoxil Dispermox Duomox Defender[28] E-Mox[29] Enhancin Ezymox[30] Gimalxina Geramox Hiconcil Himox Isimoxin[31] Klavax Klavocin Klavox Lamoxy Largopen MOX Moxatag Moxilen Moxypen Moxyvit Nobactam Novamoxin Optamox Ospamox Pamoxicillin Panklav Pinamox Penamox Polymox Senox[32] Sinacilin Skymox[33] Spektramox Starmox[34] Trimox Tolodina[35] Tormoxin Tyclav[36] Unimox Vidamox Wedemox Wymox Yucla Zerrsox Zimox Zoxicillin[3