Amoxicillin

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Amoxicillin
Amoxicillin.svg
Amoxicillin-from-xtal-3D-bs-17.png
Clinical data
Pronunciation /əˌmɒksɪˈsɪlɪn/
Trade names Amoxil, Trimox, others [1]
Other namesAmoxycillin, amox, Amoxycillin (AAN AU)
AHFS/Drugs.com Monograph
MedlinePlus a685001
License data
Pregnancy
category
  • AU:A
Routes of
administration 		By mouth, IV (bolus), intramuscular injection
Drug class β-Lactam antibiotic; Aminopenicillin
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability Oral: 60% [7]
Protein binding 17% [7]
Metabolism Hydroxylation, oxidative deamination, aliphatic chain oxidation, decarboxylation, glucuronidation [7]
Metabolites Seven [7]
Onset of action ≤1.3–1.5 hours (Tmax Tooltip time to peak concentrations) [7]
Elimination half-life 61.3 minutes (~1 hour) [7]
Excretion Urine: 70–78% (after 6 hours) [7]
Identifiers
  • (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-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.043.625 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H19N3O5S
Molar mass 365.40 g·mol−1
3D model (JSmol)
Density 1.6±0.1 [8]  g/cm3
  • O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccc(O)cc1)N)[C@H]3SC2(C)C
  • InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1 Yes check.svgY
  • Key:LSQZJLSUYDQPKJ-NJBDSQKTSA-N Yes check.svgY
   (verify)

Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections [9] such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections. [9] It is taken orally (swallowed by mouth), or less commonly by either Intramuscular injection or by an IV bolus injection, which is a relatively quick intravenous injection lasting from a couple of seconds to a few minutes. [9] [10]

Contents

Common adverse effects include nausea and rash. [9] It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea. [11] It should not be used in those who are allergic to penicillin. [9] While usable in those with kidney problems, the dose may need to be decreased. [9] Its use in pregnancy and breastfeeding does not appear to be harmful. [9] Amoxicillin is in the β-lactam family of antibiotics. [9]

Amoxicillin was discovered in 1958 and came into medical use in 1972. [12] [13] Amoxil was approved for medical use in the United States in 1974, [4] [5] and in the United Kingdom in 1977. [2] It is on the World Health Organization's List of Essential Medicines. [14] It is one of the most commonly prescribed antibiotics in children. [15] Amoxicillin is available as a generic medication. [9] In 2022, it was the 26th most commonly prescribed medication in the United States, with more than 20 million prescriptions. [16] [17]

Medical uses

Amoxicillin BP Amoxicillin.JPG
Amoxicillin BP

Amoxicillin is used in the treatment of a number of infections, including acute otitis media, streptococcal pharyngitis, pneumonia, skin infections, urinary tract infections, Salmonella infections, Lyme disease, and chlamydia infections. [9] [18]

Acute otitis media

Children with acute otitis media who are younger than six months of age are generally treated with amoxicillin or other antibiotics. Although most children with acute otitis media who are older than two years old do not benefit from treatment with amoxicillin or other antibiotics, such treatment may be helpful in children younger than two years old with acute otitis media that is bilateral or accompanied by ear drainage. [19] In the past, amoxicillin was dosed three times daily when used to treat acute otitis media, which resulted in missed doses in routine ambulatory practice. There is now evidence that two-times daily dosing or once-daily dosing has similar effectiveness. [20]

Respiratory infections

Most sinusitis infections are caused by viruses, for which amoxicillin and amoxicillin-clavulanate are ineffective, [21] and the small benefit gained by amoxicillin may be overridden by the adverse effects. [22] Amoxicillin is considered the first-line empirical treatment for most cases of uncomplicated bacterial sinusitis in children and adults when culture data is unavailable. [23] [24] [25] Amoxicillin is recommended as the preferred first-line treatment for community-acquired pneumonia in adults by the National Institute for Health and Care Excellence, either alone (mild to moderate severity disease) or in combination with a macrolide. [26] Research suggests that is as effective as co-amoxiclav (a broad-spectrum antibiotic) for people admitted to hospital with pneumonia, regardless of its severity. [27] [28] The World Health Organization (WHO) recommends amoxicillin as first-line treatment for pneumonia that is not "severe". [29] Amoxicillin is used in post-exposure inhalation of anthrax to prevent disease progression and for prophylaxis. [18]

H. pylori

It is effective as one part of a multi-drug regimen for the treatment of stomach infections of Helicobacter pylori . It is typically combined with a proton-pump inhibitor (such as omeprazole) and a macrolide antibiotic (such as clarithromycin); other drug combinations are also effective. [30]

Lyme borreliosis

Amoxicillin is effective for the treatment of early cutaneous Lyme borreliosis; the effectiveness and safety of oral amoxicillin is neither better nor worse than common alternatively-used antibiotics. [31]

Odontogenic infections

Amoxicillin is used to treat odontogenic infections, infections of the tongue, lips, and other oral tissues. It may be prescribed following a tooth extraction, particularly in those with compromised immune systems. [32]

Skin infections

Amoxicillin is occasionally used for the treatment of skin infections, [18] such as acne vulgaris. [33] It is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such as doxycycline and minocycline. [34]

Infections in infants in resource-limited settings

Amoxicillin is recommended by the World Health Organization for the treatment of infants with signs and symptoms of pneumonia in resource-limited situations when the parents are unable or unwilling to accept hospitalization of the child. Amoxicillin in combination with gentamicin is recommended for the treatment of infants with signs of other severe infections when hospitalization is not an option. [35]

Prevention of bacterial endocarditis

It is also used to prevent bacterial endocarditis and as a pain-reliever in high-risk people having dental work done, to prevent Streptococcus pneumoniae and other encapsulated bacterial infections in those without spleens, such as people with sickle-cell disease, and for both the prevention and the treatment of anthrax. [9] The United Kingdom recommends against its use for infectious endocarditis prophylaxis. [36] These recommendations do not appear to have changed the rates of infection for infectious endocarditis. [37]

Combination treatment

Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, which are resistant to most β-lactam antibiotics, such as penicillin. For this reason, it may be combined with clavulanic acid, a β-lactamase inhibitor. This drug combination is commonly called co-amoxiclav. [38]

Spectrum of activity

It is a moderate-spectrum, bacteriolytic, β-lactam antibiotic in the aminopenicillin family used to treat susceptible Gram-positive and Gram-negative bacteria. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other β-lactam antibiotics. In general, Streptococcus, Bacillus subtilis, Enterococcus, Haemophilus, Helicobacter, and Moraxella are susceptible to amoxicillin, whereas Citrobacter, Klebsiella and Pseudomonas aeruginosa are resistant to it. [39] Some E. coli and most clinical strains of Staphylococcus aureus have developed resistance to amoxicillin to varying degrees. [40]

Adverse effects

Adverse effects are similar to those for other β-lactam antibiotics, including nausea, vomiting, rashes, and antibiotic-associated colitis. Diarrhea (loose bowel movements) may also occur.

Rarer adverse effects include mental and behavioral changes, lightheadedness, insomnia, hyperactivity, agitation, confusion, anxiety, sensitivity to lights and sounds, and unclear thinking. [3] [41] [42] Immediate medical care is required upon the first signs of these adverse effects. [9] Similarly to other penicillins, amoxicillin has been associated with an increased risk of seizures. [3] [41] [43] [44] Amoxicillin-induced neurotoxicity has been especially associated with concentrations of greater than 110 mg/L. [45]

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 the fingertips and around the 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 adverse effects can be fatal due to anaphylaxis. [9]

Use of the amoxicillin/clavulanic acid combination for more than one week has caused a drug-induced immunoallergic-type hepatitis in some patients. Young children having ingested acute overdoses of amoxicillin manifested lethargy, vomiting, and renal dysfunction. [46] [47]

There is poor reporting of adverse effects of amoxicillin from clinical trials. For this reason, the severity and frequency of adverse effects from amoxicillin are probably higher than reported in clinical trials. [11]

Nonallergic rash

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 and may rarely be a component of the DRESS syndrome. [48]

The rash is described as maculopapular or morbilliform (measles-like; therefore, in medical literature, it is called "amoxicillin-induced morbilliform rash". [49] ). 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. [50] [51]

A nonallergic amoxicillin rash may also be an indicator of infectious mononucleosis. Some studies indicate about 80–90% of patients with acute Epstein–Barr virus infection treated with amoxicillin or ampicillin develop such a rash. [52]

Interactions

Amoxicillin may interact with these drugs:

When given intravenously or intramuscularly: [10]

Pharmacology

Amoxicillin (α-amino-p-hydroxybenzyl penicillin) is a semisynthetic derivative of penicillin with a structure similar to ampicillin but with better absorption when taken by mouth, thus yielding higher concentrations in blood and in urine. [58] Amoxicillin diffuses easily into tissues and body fluids. It will cross the placenta and is excreted into breastmilk in small quantities. It is metabolized by the liver and excreted into the urine. It has an onset of 30 minutes and a half-life of 3.7 hours in newborns and 1.4 hours in adults. [18]

Amoxicillin attaches to the cell wall of susceptible bacteria and results in their death. It is effective against streptococci, pneumococci, enterococci, Haemophilus influenzae , Escherichia coli, Proteus mirabilis , Neisseria meningitidis , Neisseria gonorrhoeae , Shigella , Chlamydia trachomatis , Salmonella, Borrelia burgdorferi , and Helicobacter pylori. [18] As a derivative of ampicillin, amoxicillin is a member of the penicillin family and, like penicillins, is a β-lactam antibiotic. [59] It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the bacterial cell wall. It has two ionizable groups in the physiological range (the amino group in alpha-position to the amide carbonyl group and the carboxyl group). [60]

Chemistry

Amoxicillin is a β-lactam and aminopenicillin antibiotic in terms of chemical structure. [61] [62] It is structurally related to ampicillin. [61] [62]

The experimental log P of amoxicillin is 0.87. [62] [63] It is described as an "ambiphilic"—between hydrophilic and lipophilic—antibiotic. [64]

History

Amoxicillin was one of several semisynthetic derivatives of 6-aminopenicillanic acid (6-APA) developed by the Beecham Group in the 1960s. It was invented by Anthony Alfred Walter Long and John Herbert Charles Nayler, two British scientists. [65] [66] It became available in 1972 and was the second aminopenicillin to reach the market (after ampicillin in 1961). [67] [68] [69] Co-amoxiclav became available in 1981. [68]

Society and culture

Economics

Amoxicillin is relatively inexpensive. [70] In 2022, a survey of eight generic antibiotics commonly prescribed in the United States found their average cost to be about $42.67, while amoxicillin was sold for $12.14 on average. [71]

Modes of delivery

Pharmaceutical manufacturers make amoxicillin in trihydrate form, for oral use available as capsules, regular, chewable and dispersible tablets, syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration.[ medical citation needed ]

An extended-release is available. [6] [72] The intravenous form of amoxicillin is not sold in the United States. [73] When an intravenous aminopenicillin is required in the United States, ampicillin is typically used. When there is an adequate response to ampicillin, the course of antibiotic therapy may often be completed with oral amoxicillin. [74]

Research with mice indicated successful delivery using intraperitoneally injected amoxicillin-bearing microparticles. [75]

Names

Amoxicillin is the international nonproprietary name (INN), [76] British Approved Name (BAN), and United States Adopted Name (USAN), while amoxycillin is the Australian Approved Name (AAN).[ citation needed ]

Amoxicillin is one of the semisynthetic penicillins discovered by the former pharmaceutical company Beecham Group. The patent for amoxicillin has expired, thus amoxicillin and co-amoxiclav preparations are marketed under various brand names across the world. [1]

Veterinary uses

Amoxicillin is also sometimes used as an antibiotic for animals. The use of amoxicillin for animals intended for human consumption (chickens, cattle, and swine for example) has been approved. [77]

Related Research Articles

<span class="mw-page-title-main">Ampicillin</span> Antibiotic

Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat several bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously.

β-Lactam antibiotic Class of broad-spectrum antibiotics

β-Lactam antibiotics are antibiotics that contain a β-lactam ring in their chemical structure. This includes penicillin derivatives (penams), cephalosporins and cephamycins (cephems), monobactams, carbapenems and carbacephems. Most β-lactam antibiotics work by inhibiting cell wall biosynthesis in the bacterial organism and are the most widely used group of antibiotics. Until 2003, when measured by sales, more than half of all commercially available antibiotics in use were β-lactam compounds. The first β-lactam antibiotic discovered, penicillin, was isolated from a strain of Penicillium rubens.

<span class="mw-page-title-main">Amoxicillin/clavulanic acid</span> Combination antibiotic medication

Amoxicillin/clavulanic acid, also known as co-amoxiclav or amox-clav, sold under the brand name Augmentin, among others, is an antibiotic medication used for the treatment of a number of bacterial infections. It is a combination consisting of amoxicillin, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor. It is specifically used for otitis media, streptococcal pharyngitis, pneumonia, cellulitis, urinary tract infections, and animal bites. It is taken by mouth or by injection into a vein.

<span class="mw-page-title-main">Cefalexin</span> Beta-lactam antibiotic

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections. It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall. Cefalexin is a β-lactam antibiotic within the class of first-generation cephalosporins. It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.

<span class="mw-page-title-main">Meropenem</span> Broad-spectrum antibiotic

Meropenem, sold under the brand name Merrem among others, is an intravenous carbapenem antibiotic used to treat a variety of bacterial infections. Some of these include meningitis, intra-abdominal infection, pneumonia, sepsis, and anthrax.

<span class="mw-page-title-main">Cefaclor</span> Chemical compound

Cefaclor, sold under the trade name Ceclor among others, is a second-generation cephalosporin antibiotic used to treat certain bacterial infections such as pneumonia and infections of the ear, lung, skin, throat, and urinary tract. It is also available from other manufacturers as a generic.

<span class="mw-page-title-main">Carbapenem</span> Class of highly effective antibiotic agents

Carbapenems are a class of very effective antibiotic agents most commonly used for treatment of severe bacterial infections. This class of antibiotics is usually reserved for known or suspected multidrug-resistant (MDR) bacterial infections. Similar to penicillins and cephalosporins, carbapenems are members of the beta-lactam antibiotics drug class, which kill bacteria by binding to penicillin-binding proteins, thus inhibiting bacterial cell wall synthesis. However, these agents individually exhibit a broader spectrum of activity compared to most cephalosporins and penicillins. Furthermore, carbapenems are typically unaffected by emerging antibiotic resistance, even to other beta-lactams.

<span class="mw-page-title-main">Cefotaxime</span> Chemical compound

Cefotaxime is an antibiotic used to treat several bacterial infections in humans, other animals, and plant tissue culture. Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

Ampicillin/sulbactam is a fixed-dose combination medication of the common penicillin-derived antibiotic ampicillin and sulbactam, an inhibitor of bacterial beta-lactamase. Two different forms of the drug exist. The first, developed in 1987 and marketed in the United States under the brand name Unasyn, generic only outside the United States, is an intravenous antibiotic. The second, an oral form called sultamicillin, is marketed under the brand name Ampictam outside the United States, and generic only in the United States. Ampicillin/sulbactam is used to treat infections caused by bacteria resistant to beta-lactam antibiotics. Sulbactam blocks the enzyme which breaks down ampicillin and thereby allows ampicillin to attack and kill the bacteria.

<span class="mw-page-title-main">Sultamicillin</span> Chemical compound

Sultamicillin, sold under the brand name Unasyn among others, is an oral form of the penicillin antibiotic combination ampicillin/sulbactam. It is used for the treatment of bacterial infections of the upper and lower respiratory tract, the kidneys and urinary tract, skin and soft tissues, among other organs. It contains esterified ampicillin and sulbactam.

<span class="mw-page-title-main">Flucloxacillin</span> Penicillin

Flucloxacillin, also known as floxacillin, is an antibiotic used to treat skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone. It may be used together with other medications to treat pneumonia, and endocarditis. It may also be used prior to surgery to prevent Staphylococcus infections. It is not effective against methicillin-resistant Staphylococcus aureus (MRSA). It is taken by mouth or given by injection into a vein or muscle.

<span class="mw-page-title-main">Ampicillin/flucloxacillin</span> Combination drug

Ampicillin/flucloxacillin (INNs) also known as co-fluampicil (BAN), and sold under the tradename Magnapen, is a combination drug of the two β-lactam antibiotics, ampicillin and flucloxacillin, both in equal amounts, available in a capsule and as a liquid, both taken by mouth, and as a formulation which can be given by injection into muscle or vein.

<span class="mw-page-title-main">Dicloxacillin</span> Chemical compound

Dicloxacillin is a narrow-spectrum β-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible (non-resistant) Gram-positive bacteria. It is active against beta-lactamase-producing organisms such as Staphylococcus aureus, which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).

<span class="mw-page-title-main">Cefdinir</span> Chemical compound

Cefdinir, sold under the brand name Omnicef among others, is an antibiotic used to treat pneumonia, otitis media, strep throat, and cellulitis. It is a less preferred option for pneumonia, otitis media, and strep throat which may be used in those with a severe penicillin allergy. It is taken by mouth.

<span class="mw-page-title-main">Cefditoren</span> Chemical to treat skin infections

Cefditoren, also known as cefditoren pivoxil is an antibiotic used to treat infections caused by Gram-positive and Gram-negative bacteria that are resistant to other antibiotics. It is mainly used for treatment of community acquired pneumonia. It is taken by mouth and is in the cephalosporin family of antibiotics, which is part of the broader beta-lactam group of antibiotics.

β-Lactamase inhibitor Drugs that inhibit β-Lactamase enzymes

Beta-lactamases are a family of enzymes involved in bacterial resistance to beta-lactam antibiotics. In bacterial resistance to beta-lactam antibiotics, the bacteria have beta-lactamase which degrade the beta-lactam rings, rendering the antibiotic ineffective. However, with beta-lactamase inhibitors, these enzymes on the bacteria are inhibited, thus allowing the antibiotic to take effect. Strategies for combating this form of resistance have included the development of new beta-lactam antibiotics that are more resistant to cleavage and the development of the class of enzyme inhibitors called beta-lactamase inhibitors. Although β-lactamase inhibitors have little antibiotic activity of their own, they prevent bacterial degradation of beta-lactam antibiotics and thus extend the range of bacteria the drugs are effective against.

<span class="mw-page-title-main">Ciclacillin</span> Chemical compound

Ciclacillin (INN) or cyclacillin (USAN), trade names Cyclapen, Cyclapen-W, Vastcillin, and others, is an aminopenicillin antibiotic. Its spectrum of activity is similar to that of ampicillin, although it is less susceptible to beta-lactamases than ampicillin and has much higher bioavailability. A large randomized, double-blind clinical trial published in 1978 also showed that ciclacillin is associated with significantly fewer and milder adverse effects than ampicillin; later studies seemed to confirm this improved tolerability, at least in children.

<span class="mw-page-title-main">Aminopenicillin</span> Group of antibiotics

The aminopenicillins are a group of antibiotics in the penicillin family that are structural analogs of ampicillin. Like other penicillins and beta-lactam antibiotics, they contain a beta-lactam ring that is crucial to its antibacterial activity.

There are many circumstances during dental treatment where antibiotics are prescribed by dentists to prevent further infection. The most common antibiotic prescribed by dental practitioners is penicillin in the form of amoxicillin, however many patients are hypersensitive to this particular antibiotic. Therefore, in the cases of allergies, erythromycin is used instead.

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