Amoxicillin

Source: Wikipedia, the free encyclopedia.
Not to be confused with Ampicillin.

Amoxicillin
Clinical data
Pronunciation/əˌmɒksɪˈsɪlɪn/
Trade namesAmoxil, Trimox, others[1]
Other namesAmoxycillin, amox, Amoxycillin (AAN AU)
AHFS/Drugs.comMonograph
MedlinePlusa685001
License data
Pregnancy
category
  • AU: A
QG51AA03 (WHO)
Legal status
Legal status
Kidneys
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
JSmol)
Density1.6±0.1 [7] 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 checkY
  • Key:LSQZJLSUYDQPKJ-NJBDSQKTSA-N checkY
  (verify)

Amoxicillin is an

odontogenic infections, and urinary tract infections.[8] It is taken by mouth, or less commonly by injection.[8][9]

Common adverse effects include nausea and rash.

kidney problems, the dose may need to be decreased.[8] Its use in pregnancy and breastfeeding does not appear to be harmful.[8] Amoxicillin is in the β-lactam family of antibiotics.[8]

Amoxicillin was discovered in 1958 and came into medical use in 1972.

generic medication.[8] In 2021, it was the 38th most commonly prescribed medication in the United States, with more than 16 million prescriptions.[16][17]

Medical uses

Amoxicillin BP

Amoxicillin is used in the treatment of a number of infections, including

chlamydia infections.[8][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] The World Health Organization (WHO) recommends amoxicillin as first-line treatment for pneumonia that is not "severe".[27] 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 treatment of stomach infections of

macrolide antibiotic (such as clarithromycin); other drug combinations are also effective.[28]

Lyme borreliosis

Amoxicillin is effective for treatment of early cutaneous

Lyme borreliosis; the effectiveness and safety of oral amoxicillin is neither better nor worse than common alternatively-used antibiotics.[29]

Odontogenic infections

Amoxicillin is used to treat

compromised immune systems.[30]

Skin infections

Amoxicillin is occasionally used for the treatment of skin infections,

acne vulgaris.[31] It is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such as doxycycline and minocycline.[32]

Infections in infants in resource-limited settings

Amoxicillin is recommended by the World Health Organization for the treatment of

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.[33]

Prevention of bacterial endocarditis

It is also used to prevent

sickle-cell disease, and for both the prevention and the treatment of anthrax.[8] The United Kingdom recommends against its use for infectious endocarditis prophylaxis.[34] These recommendations do not appear to have changed the rates of infection for infectious endocarditis.[35]

Combination treatment

Amoxicillin is susceptible to degradation by

co-amoxiclav.[36]

Spectrum of activity

It is a

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.[37] Some E. coli and most clinical strains of Staphylococcus aureus have developed resistance to amoxicillin to varying degrees.[38]

Adverse effects

β-lactam antibiotics, including nausea, vomiting, rashes, and antibiotic-associated colitis. Loose bowel movements (diarrhea) may also occur. Rarer adverse 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 adverse effects.[8]

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 adverse effects can be fatal due to anaphylaxis.[8]

Use of the amoxicillin/clavulanic acid combination for more than one week has caused a drug-induced immunoallergic-type

renal dysfunction.[39][40]

There is poor reporting of adverse effects of amoxicillin from clinical trials. For this reason, the severity and frequency of adverse effects from amoxicillin is probably higher than reported from clinical trials.[10]

Nonallergic rash

Between 3 and 10% of children taking amoxicillin (or

DRESS syndrome.[41]

The rash is described as

maculopapular or morbilliform (measles-like; therefore, in medical literature, it is called "amoxicillin-induced morbilliform rash".[42]). 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.[43][44]

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.[45]

  • Nonallergic amoxicillin rash eight days after first dose: This photo was taken 24 hours after the rash began.
    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.
    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.
    At 23 hours after the first photo, the color appears to be fading, and much of rash has spread to confluence.

Interactions

Amoxicillin may interact with these drugs:

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.

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

β-lactam antibiotic.[52] It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the bacterial cell wall
. It has two
carboxyl group).[53]

History

See also: Timeline of antibiotics

Amoxicillin was one of several

Co-amoxiclav became available in 1981.[57]

Society and culture

Economics

Amoxicillin is relatively inexpensive.[59] 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.[60]

Modes of delivery

Pharmaceutical manufacturers make amoxicillin in tri

intravenous administration.[medical citation needed
]

An

extended-release is available.[6][61] The intravenous form of amoxicillin is not sold in the United States.[62] 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.[63]

Research with mice indicated successful delivery using

microparticles.[64]

Names

"Amoxicillin" is the

International Nonproprietary Name (INN), 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 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

swine for example) has been approved.[65]

References

  1. ^ a b "International brand names for amoxicillin". Drugs.com. Archived from the original on 29 May 2016. Retrieved 15 November 2016.
  2. ^ a b "Amoxil Vials for Injection 500mg - Summary of Product Characteristics (SmPC)". (emc). 4 November 2021. Archived from the original on 10 October 2022. Retrieved 8 October 2022.
  3. ^ "Amoxil (amoxicillin) Capsules, Tablets, Chewable Tablets, and Powder for Oral Suspension". DailyMed. Retrieved 8 October 2022.
  4. ^ a b "Amoxil: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 8 October 2022.
  5. ^ a b "Trimox: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 8 October 2022.
  6. ^ a b "Moxatag (amoxicillin extended-release) Tablets Initial U.S. Approval: 1974". DailyMed. Retrieved 8 October 2022.
  7. ^ "Amoxicillin". www.chemsrc.com.
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  9. ^ "Amoxicillin Sodium for Injection". EMC. 10 February 2016. Archived from the original on 27 October 2016. Retrieved 26 October 2016.
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  18. ^ a b c d e f "Amoxicillin" (PDF). Davis. 2017. Archived (PDF) from the original on 8 September 2017. Retrieved 22 March 2017.
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Further reading

  • Neal MJ (2002). Medical Pharmacology at a Glance (4th ed.). Oxford: Blackwell Science.
    ISBN 978-0-632-05244-8
    .
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