Amoxicillin

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Amoxicillin

Systematic (IUPAC) name

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

Clinical data

Trade names

Actimoxi, Alphamox, Amocla,Tycil, Amoxil, Trimox, among others

AHFS/Drugs.com

monograph

MedlinePlus

a685001

Pregnancy cat.

A (AU) B (US)

Legal status

POM (UK) -only (US)

Routes

Oral, intravenous

Pharmacokinetic data

Bioavailability

95% oral

Metabolism

less than 30% biotransformed in liver

Half-life

61.3 minutes

Excretion

renal

Identifiers

CAS number

26787-78-0

ATC code

J01CA04 QG51AA03

PubChem

CID 33613

DrugBank

DB01060

ChemSpider

31006

UNII

9EM05410Q9

KEGG

D07452

ChEBI

CHEBI:2676

ChEMBL

CHEMBL1082

Chemical data

Formula

C16H19N3O5S

Mol. mass

365.4 g/mol

SMILES[show]

InChI[show]

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Amoxicillin BP

Amoxicillin (INN), formerly amoxycillin (BAN), and abbreviated amox, is a moderate-spectrum, bacteriolytic, -lactam antibiotic used to treat bacterial infections caused by susceptiblemicroorganisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other -lactam antibiotics. Amoxicillin is one of the most commonantibiotics prescribed for children. The drug became available in 1972. Amoxicillin is susceptible to degradation by -lactamase-producing bacteria, which are resistant to a broad spectrum of -lactam antibiotics, such as penicillin. For this reason, it is often combined withclavulanic acid, a -lactamase inhibitor. This increases effectiveness by reducing its susceptibility to -lactamase resistance.

Medical uses
Amoxicillin is used in the treatment of a number of infections, including acute otitis media,Streptococcal pharyngitis, pneumonia, skin infections, urinary-tract infections, Salmonella, lyme disease, [1] and chlamydia infections. It is also used to prevent bacterial endocarditis in high-risk people who are having dental work done, to prevent strep pneumococus infections in those withoutspleens, and for both [1] the prevention and the treatment of anthrax. The United Kingdom recommends against its use for [2] infectious endocarditis prophylaxis. These recommendations have not appeared to have changed the [3] rates of infection. Amoxicillin and amoxicillin-clavulanate are recommended by guidelines as the first-choice drug for [4][5] bacterial sinusitis. Most sinusitis is caused by viruses, for which these drugs are ineffective. Amoxicillin [6] is occasionally used for the treatment of skin infections, such as acne vulgaris. Amoxicillin is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such [7] as doxycycline and minocycline. [edit]Adverse

effects

Side-effects are as those for other beta-lactam antibiotics. Side-effects include nausea, vomiting, rashes, and antibiotic-associated colitis. 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 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. 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 who are allergic to amoxicillin the side-effects can be deadly. Use of the amoxicillin/clavulanic acid combination for more than one week has caused mild hepatitis in some patients. Young children having ingested acute overdoses of amoxicillin manifested lethargy, [8][9] vomiting and renal dysfunction. [edit]Nonallergic

amoxicillin rash

Somewhere between 3% and 10% of children taking amoxicillin (or ampicillin) 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 as maculopapular or morbilliform (measles-like; therefore, in medical literature, it is [10] called "amoxicillin-induced morbilliform rash" ). 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, and therefore a [11][12] healthcare professional is often required to distinguish between the two. A nonallergic amoxicillin rash may also be an indicator of infectious mononucleosis: Some studies indicate approximately 80-90% of patients with acute Epstein Barr virus infection treated with amoxicillin [13] or ampicillin develop such a rash.

Nonallergic amoxicillin rash 8 days after first dose, 24 hours after rash began. Diagnosed by a pediatric resident at local university hospital.

Eight hours after first photo, individual spots have grown and begun to merge.

Twenty-three hours after first photo, the color appears to be fading, and much of rash has spread to confluence.

[edit]Interaction Amoxicillin may interact with the following groups of drugs: Anticoagulants (e.g. warfarin, pradaxa) Allopurinol (gout treatment)
[14]

Birth control pills

[citation needed]

Certain antibiotics Cancer treatment (methotrexate) Uricosuric drugs Typhoid vaccine

[edit]Mechanism

of action

Main article: Beta-lactam antibiotic This drug 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 walls of both Grampositive and Gram-negative bacteria. It has two ionizable groups in the physiological range (the amino group in alpha-position to the amide carbonyl group and the carboxyl group). [edit]Spectrum

of bacterial susceptibility and resistance

Streptococcus", Bacillus subtilis, Enterococcus, Haemophilus, Helicobacter and Moraxella species are generally susceptible to amoxicillin, whileCitrobacter, Klebsiella and Pseudomonas aeruginosa are [15] resistant to amoxicillin. Some E. coli and most clinical isolates of Staphylococcus aureus have developed resistance to amoxicillin to varying degrees. [edit]History See also: Timeline of antibiotics Amoxicillin was one of several semisynthetic derivatives of 6-aminopenicillanic acid (6-APA) developed at Beecham in the 1960s. It became available in 1972, and was the second aminopenicillin to reach the [16][17] [16] market (after ampicillin in 1961). Co-amoxiclav became available in 1981. [edit]Formulations [edit]Modes

of delivery

Pharmaceutical manufacturers make amoxicillin in trihydrate form available as capsules, chewable and dispersible tablets plus syrup and pediatricsuspension for oral use, and as the sodium salt [full citation for intravenous administration, although the IV formulation is not available in the United States.
needed]

Amoxicillin is most commonly taken orally. The liquid forms are helpful where the patient might find it difficult to take tablets or capsules. Research with mice (published in 2010) indicates successful delivery using intraperitoneally injected [18] amoxicillin-bearing microparticles.