Difference between revisions of "Amoxicillin"
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| IUPAC_name = (2''S'',5''R'',6''R'')- 6-{[(2''R'')-2-amino- 2-(4-hydroxyphenyl)- acetyl]amino}- 3,3-dimethyl- 7-oxo- 4-thia- 1-azabicyclo[3.2.0]heptane- 2-carboxylic acid | | IUPAC_name = (2''S'',5''R'',6''R'')- 6-{[(2''R'')-2-amino- 2-(4-hydroxyphenyl)- acetyl]amino}- 3,3-dimethyl- 7-oxo- 4-thia- 1-azabicyclo[3.2.0]heptane- 2-carboxylic acid | ||
| − | | image = | + | | image = Amoxicillin.svg |
| image2= Amoxicillin-3D-balls.png | | image2= Amoxicillin-3D-balls.png | ||
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[[Image:Amoxicillin.JPG|thumb|right|Amoxicillin BP]] | [[Image:Amoxicillin.JPG|thumb|right|Amoxicillin BP]] | ||
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| − | '''Amoxicillin''' ([[International Nonproprietary Name|INN]]), formerly '''amoxycillin''' ([[British Approved Name|BAN]]), abbreviated '''Amox''','''Tormoxin (in India)''', is a moderate-spectrum, bacteriolytic, [[beta-lactam antibiotic|β-lactam]] [[antibiotic]] used to treat [[bacterial]] [[infection]]s caused by susceptible [[microorganism]]s. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other β-lactam antibiotics. It is also a treatment for cystic acne.<ref>{{cite web | title = Adolescent Acne: Management | url = http://www.medscape.com/viewarticle/430534_5}}</ref> | + | '''Amoxicillin''' ([[International Nonproprietary Name|INN]]), formerly '''amoxycillin''' ([[British Approved Name|BAN]]), '''amoxycillin''' (cilamox) in Australia<ref name="racgp">[http://www.racgp.org.au/cmi/txcamoxc.pdf], Royal Australian College of General Practitioners Leaflet.</ref>, abbreviated '''Amox''','''Tormoxin (in India)''', is a moderate-spectrum, bacteriolytic, [[beta-lactam antibiotic|β-lactam]] [[antibiotic]] used to treat [[bacterial]] [[infection]]s caused by susceptible [[microorganism]]s. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other β-lactam antibiotics. It is also a treatment for cystic acne.<ref>{{cite web | title = Adolescent Acne: Management | url = http://www.medscape.com/viewarticle/430534_5}}</ref> |
| − | Amoxicillin is susceptible to degradation by [[beta-lactamase|β-lactamase]]-producing bacteria, | + | Amoxicillin is susceptible to degradation by [[beta-lactamase|β-lactamase]]-producing bacteria, which are resistant to a broad spectrum of β-lactam antibiotics, such as penicillin. For this reason it is often combined with [[clavulanic acid]], a β-lactamase inhibitor, and marketed under one name. This increases effectiveness by reducing its susceptibility to β-lactamase resistance. |
==Mode of action== | ==Mode of action== | ||
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== Side effects == | == Side effects == | ||
[[Adverse drug reaction|Side effect]]s are as those for other [[Beta-lactam antibiotic#Adverse effects|beta-lactam antibiotic]]s. | [[Adverse drug reaction|Side effect]]s are as those for other [[Beta-lactam antibiotic#Adverse effects|beta-lactam antibiotic]]s. | ||
| − | Side effects include [[nausea]], vomiting, rashes, and antibiotic-associated colitis. Loose bowel movements (diarrhea) also may occur. | + | Side effects include [[nausea]], vomiting, rashes, and antibiotic-associated colitis. Loose bowel movements (diarrhea) also may occur. Rarer but patient reported side effects include mental changes, lightheadedness, confusion, anxiety, sensitivity to lights and sounds, 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. | 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. | ||
| + | |||
| + | Use of the amoxicillin/clavulanic acid combination for more than one week has caused moderate to severe [[hepatitis]] in a number of patients. Young children who ingested acute overdoses of amoxicillin manifested [[lethargy]], vomiting and [[Renal failure|renal dysfunction]].<ref>Cundiff J, Joe S. Amoxicillin-clavulanic acid-induced hepatitis. Amer. J. Otolaryngol. 28: 28-30, 2007.</ref><ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 81-83.</ref> | ||
===Non-allergic amoxicillin rash=== | ===Non-allergic amoxicillin rash=== | ||
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==External links== | ==External links== | ||
| − | * [http://www.med.umich.edu/1libr/pa/pa_ampirash_hhg.htm University of Michigan Mott's Children's Hospital article about "amoxicillin rash."] | + | * [http://www.med.umich.edu/1libr/pa/pa_ampirash_hhg.htm University of Michigan Mott's Children's Hospital article about "amoxicillin rash."] (Very similar to Schmitt 2005 content) |
* [http://www.amoxicillinsideeffects.net/ Amoxicillin Side Effect Experiences] | * [http://www.amoxicillinsideeffects.net/ Amoxicillin Side Effect Experiences] | ||
* [http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Amoxicillin+anhydrous U.S. National Library of Medicine: Drug Information Portal - Amoxicillin] | * [http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Amoxicillin+anhydrous U.S. National Library of Medicine: Drug Information Portal - Amoxicillin] | ||
Revision as of 19:36, 19 September 2010
 | This article includes a list of references, related reading or external links, but its sources remain unclear because it lacks inline citations. Please improve this article by introducing more precise citations. (August 2009) |
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File:Amoxicillin.JPG Amoxicillin BP | ||||||||||||||||||||||||||||||||||||||||||||||||||
Amoxicillin (INN), formerly amoxycillin (BAN), amoxycillin (cilamox) in Australia[1], abbreviated Amox,Tormoxin (in India), is a moderate-spectrum, bacteriolytic, β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other β-lactam antibiotics. It is also a treatment for cystic acne.[2]
Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, which are resistant to a broad spectrum of β-lactam antibiotics, such as penicillin. For this reason it is often combined with clavulanic acid, a β-lactamase inhibitor, and marketed under one name. This increases effectiveness by reducing its susceptibility to β-lactamase resistance.
Contents
Mode of action
Amoxicillin acts by inhibiting the synthesis of bacterial cell wall. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell walls of both Gram-positive and Gram-negative bacteria
Formulations
Amoxicillin in trihydrate form is available as capsules, chewable and dispersible tablets plus syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration (although the IV formulation is not available in the United States[3]). It is one of the most common antibiotics prescribed for children, and the liquid forms are helpful where the patient might find it difficult to take tablets or capsules. It has three ionizable groups. A once daily dosing form (Moxatag) was approved by the American FDA in January 2008.
Side 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) also may occur. Rarer but patient reported side effects include mental changes, lightheadedness, confusion, anxiety, sensitivity to lights and sounds, 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.
Use of the amoxicillin/clavulanic acid combination for more than one week has caused moderate to severe hepatitis in a number of patients. Young children who ingested acute overdoses of amoxicillin manifested lethargy, vomiting and renal dysfunction.[4][5]
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) often itchy rash [1][2], 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, "amoxicillin-induced morbilliform rash"[6]). It starts on the trunk and can spread from there. 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)
A non-allergic amoxicillin rash may also be an indicator of infectious mononucleosis: Some studies indicate that approximately 80-90% of patients with acute Epstein Barr virus infection treated with amoxicillin or ampicillin develop such a rash.[7]
- Amoxicillin rash 3 hours after 17th dose.JPG
Non-allergic amoxicillin rash 8 days after first dose, 24 hours after rash began. Diagnosed by pediatric resident at local university hospital.
- Amoxicillin rash 11 hours after 17th dose.JPG
8 hours after first photo. Individual spots have grown and begun to merge.
- Amoxicillin rash 26 hours after 17th dose.JPG
23 hours after first photo. Color apparently fading, much of rash has spread to confluence.
Proprietary preparations
 | This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (February 2010) |
Amoxicillin is one of the semi-synthetic penicillins discovered by Beecham scientists. The patent for amoxicillin has expired, thus amoxicillin is marketed under many trade names, including:', Actimoxi, Alphamox, Amocla, AMK, Amoksibos, Amoxiclav Sandoz, Amoxidal, Amoxil, Amoxin, Amoksiklav, Amoxibiotic, Amoxicilina, Apo-Amoxi, Augmentin (with clavulanic acid), Bactox, Betalaktam, Cilamox, Curam, Dedoxil, Dispermox, Duomox, E-Mox, Enhancin, Gimalxina, Geramox, Hiconcil, Isimoxin, Klavox, Lamoxy, Moxatag, Moxilen, Moxypen, Moxyvit, Nobactam, Novamoxin, Ospamox, Panklav, Pamoxicillin, Panamox, Polymox, Samthongcillin, Clamoxyl, Senox, Sinacilin, Trimox, Tolodina, Tormoxin (India), Wymox, Yucla, Zerrsox and Zimox.
References
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- Neal, M. J. (2002). Medical pharmacology at a glance (4th ed.). Oxford: Blackwell Science. ISBN 0-632-05244-9.
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- Schmitt, Barton D. (2005). Your child's health: the parents' one-stop reference guide to symptoms, emergencies, common illnesses, behavior problems, healthy development (2nd ed.). New York: Bantam Books. ISBN 0-553-38369-8.
- British National Formulary 45 March 2003
Footnotes
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- University of Michigan Mott's Children's Hospital article about "amoxicillin rash." (Very similar to Schmitt 2005 content)
- Amoxicillin Side Effect Experiences
- U.S. National Library of Medicine: Drug Information Portal - Amoxicillin
bg:Амоксицилин ca:Amoxicil·lina da:Amoxicillin de:Amoxicillin es:Amoxicilina eu:Amoxizilina fa:آموکسی سیلین fr:Amoxicilline gl:Amoxicilina ko:아목시실린 it:Amoxicillina he:אמוקסיצילין hu:Amoxicillin nl:Amoxicilline ja:アモキシシリン pl:Amoksycylina pt:Amoxicilina ro:Amoxicilină ru:Амоксициллин sk:Amoxicilín sr:Амоксицилин su:Amoxicillin fi:Amoksisilliini sv:Amoxicillin th:อะม็อกซีซิลลิน tr:Amoksisilin uk:Амоксицилін
zh:阿莫西林- ↑ [3], Royal Australian College of General Practitioners Leaflet.
- ↑ "Adolescent Acne: Management".
- ↑ www.UpToDate.com
- ↑ Cundiff J, Joe S. Amoxicillin-clavulanic acid-induced hepatitis. Amer. J. Otolaryngol. 28: 28-30, 2007.
- ↑ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 81-83.
- ↑ e.g. Role of delayed cellular hypersensitivity and adhesion molecules in amoxicillin-induced morbilliform rashes
- ↑ Kagan, B (1977). "Ampicillin rash". Western Journal of Medicine. 126 (4): 333–335. PMC 1237570 Freely accessible. PMID 855325.
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