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Amoxicillin

1
Amoxicillin
Amoxicillin
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 names Actimoxi, Alphamox, Amocla,Tycil, Amoxil, Trimox, among others
AHFS/Drugs.com
monograph
[1]
MedlinePlus
a685001
[2]
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
[3]

ATC code
J01CA04
[4]
QG51AA03
[5]
PubChem
CID 33613
[6]
DrugBank
DB01060
[7]
ChemSpider
31006
[8]

UNII
9EM05410Q9
[9]

KEGG
D07452
[10]

ChEBI
CHEBI:2676
[11]

Amoxicillin
2
ChEMBL
CHEMBL1082
[12]

Chemical data
Formula C
16
H
19
N
3
O
5
S
Mol. mass 365.4 g/mol
(what is this?) (verify)
[13]
Amoxicillin BP
Amoxicillin (INN, BAN), or amoxycillin (AAN), and abbreviated
amox, is an antibiotic useful for the treatment of a number of bacterial
infections.
It is a moderate-spectrum, bacteriolytic, -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
-lactam antibiotics.
Amoxicillin is susceptible to degradation by -lactamase-producing
bacteria, which are resistant to a narrow spectrum of -lactam
antibiotics, such as penicillin. For this reason, it is often combined with clavulanic acid, a -lactamase inhibitor. This
increases effectiveness by reducing its susceptibility to -lactamase resistance.
Amoxicillin is one of the most common antibiotics prescribed for children. The drug first became available in 1972.
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed
in a basic health system.
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 infections, Lyme disease, and chlamydia
infections. It is also used to prevent bacterial endocarditis 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. The United Kingdom recommends
against its use for infectious endocarditis prophylaxis. These recommendations have not appeared to have changed
the rates of infection for infectious endocarditis.
Amoxicillin and amoxicillin-clavulanate are recommended by guidelines as the first-choice drug for bacterial
sinusitis, but most sinusitis is caused by viruses, for which amoxicillin and amoxicillin-clavulanate are ineffective.
Amoxicillin is occasionally used for the treatment of skin infections, such as acne vulgaris. It is often an effective
treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such as doxycycline and
minocycline.
Amoxicillin
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Adverse effects
Side-effects are similar to those for other beta-lactam antibiotics, including 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 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 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, vomiting, and renal
dysfunction.
Nonallergic amoxicillin 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.
The rash is described as maculopapular or morbilliform (measles-like; therefore, in medical literature, it is 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, so a 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 about
80-90% of patients with acute Epstein Barr virus infection treated with amoxicillin or ampicillin develop such a rash.
Nonallergic amoxicillin rash
eight days after first dose, 24
hours after rash began
Eight hours after first photo,
individual spots have grown and
begun to merge.
At 23 hours after first photo, the color appears
to be fading, and much of rash has spread to
confluence.
Amoxicillin
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Interaction
Amoxicillin may interact with these drugs:
Anticoagulants (e.g., warfarin, dabigatran)
[14]
Allopurinol (gout treatment)
Certain antibiotics
Cancer treatment (methotrexate)
Uricosuric drugs
Typhoid vaccine
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 Gram-positive 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).
Spectrum of microorganism susceptibility and resistance
In general, Streptococcus, Bacillus subtilis, Enterococcus, Haemophilus, Helicobacter, and Moraxella are
susceptible to amoxicillin, whereas Citrobacter, Klebsiella and Pseudomonas aeruginosa are resistant to it. Some E.
coli and most clinical isolates of Staphylococcus aureus have developed resistance to amoxicillin to varying degrees.
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 market (after
ampicillin in 1961).
[15]
Co-amoxiclav became available in 1981.
Formulations
Modes of delivery
Pharmaceutical manufacturers make amoxicillin in trihydrate form, available as capsules, chewable and dispersible
tablets, syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration.
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 indicated successful delivery using intraperitoneally injected amoxicillin-bearing microparticles.
Amoxicillin
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Brand names
Novamoxin prescription drug500mg
Amoxicillin trihydrate
Amoxicillin is one of the semisynthetic penicillins discovered by
Beecham scientists. 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
[16]
Alphamox
Amimox
Amocla
AMK
Amoksiklav
Amorion
Amoxibos
Amoxiclav
Amoxidal
Amoxil
Amoxin
Amoxibiotic
[17]
Amoxicilina
Amoxidal
Apo-Amoxi
Arsogil
[18]
Augmentin
Bactox
Bioxidona
[19]
Cilamox
Clamoxyl
Clavamox
Clonamox
Curam
Dedoxil
Dispermox
Duomox
Defender
[20]
E-Mox
[21]
Enhancin
Ezymox
[22]
Gimalxina
Geramox
Hiconcil
Isimoxin
[23]
Klavax
Klavocin
Klavox
Lamoxy
Largopen
Amoxicillin
6
MOX
Moxatag
Moxilen
Moxypen
Moxyvit
Nobactam
Novamoxin
Optamox
Ospamox
Pamoxicillin
Panklav
Pinamox
Penamox
Polymox
Senox
[24]
Sinacilin
Skymox
[25]
Spektramox
Starmox
[26]
Trimox
Tolodina
[27]
Tormoxin
Tyclav
[28]
Unimox
Vidamox
Wedemox
Wymox
Yucla
Zerrsox
Zimox
Zoxicillin
[29]
Names without individual reference are referenced at.
[30]
References
[1] http:/ / www. drugs. com/ monograph/ amoxicillin. html
[2] http:/ / www. nlm. nih.gov/ medlineplus/ druginfo/ meds/ a685001. html
[3] http:/ / www. nlm. nih.gov/ cgi/ mesh/ 2009/ MB_cgi?term=26787-78-0& rn=1
[4] http:/ / www. whocc.no/ atc_ddd_index/ ?code=J01CA04
[5] http:/ / www. whocc.no/ atcvet/ atcvet_index/ ?code=QG51AA03
[6] http:/ / pubchem. ncbi. nlm.nih. gov/ summary/ summary. cgi?cid=33613
[7] http:/ / www. drugbank. ca/ drugs/ DB01060
[8] http:/ / www. chemspider.com/ Chemical-Structure.31006. html
[9] http:/ / fdasis.nlm. nih. gov/ srs/ srsdirect. jsp?regno=9EM05410Q9
[10] http:/ / www.kegg. jp/ entry/ D07452
[11] https:/ / www.ebi.ac. uk/ chebi/ searchId.do?chebiId=CHEBI:2676
[12] https:/ / www.ebi.ac. uk/ chembldb/ index.php/ compound/ inspect/ CHEMBL1082
[13] http:/ / en. wikipedia. org/ w/ index. php?title=Special:ComparePages& rev1=455343638& page2=Amoxicillin
[14] [14] British National Formulary 57 March 2009
[15] [15] Geddes AM et al. Introduction: historical perspective and development of amoxicillin/clavulanate. Int J Antimicrob Agents. 2007 Dec;30
Suppl 2:S109-12. PMID 17900874
Amoxicillin
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[16] Catalog.md: Actimoxi (http:/ / www.catalog.md/ drugs/ actimoxi. html) Linked 2013-12-09
[17] Catalog.md: Amoxibiotic (http:/ / www. catalog. md/ drugs/ amoxibiotic. html) Linked 2013-12-09
[18] Aversi (Georgia): Arsogil (http:/ / www.aversi.ge/ annotations. php?id=73& lang=geo& drug_id=44400) Linked 2013-12-09
[19] Catalog.md: Bioxidona (http:/ / www.catalog.md/ drugs/ bioxidona. html) Linked 2013-12-09
[20] DrugsUpdate India: Defender from Sac Pharma (http:/ / www. drugsupdate. com/ brand/ generic/ Amoxicillin + Clavulanic Acid/ 45673)
Linked 2013-12-09
[21] Eipico (Egypt): E-Mox (http:/ / www.eipico.com.eg/ PRODUCT. ASP?id1=4& id2=1 & id4=2) Linked 2013-12-09
[22] DrugsUpdate India: Ezymox from Sac Pharma (http:/ / www. drugsupdate. com/ brand/ generic/ Amoxicillin/ 45866) Linked 2013-12-09
[23] Catalog.md: Isimoxin (http:/ / www.catalog.md/ drugs/ isimoxin. html) Linked 2013-12-09
[24] BioPortal: Senox (http:/ / bioportal.bioontology. org/ ontologies/ RXNORM?p=classes& conceptid=http:/ / purl. bioontology. org/
ontology/ RXNORM/ 205721) Linked 2013-12-09
[25] PalMediNet: Skymox (http:/ / www. pakmedinet.com/ trade. php?id=1449) Linked 2013-12-09
[26] Sarthak Biotech India: Starmox (http:/ / www. sarthakasia. com/ sarthakbiotech/ tablets. htm) Linked 2013-12-09
[27] Catalog.md: Tolodina (http:/ / www.catalog.md/ drugs/ tolodina. html) Linked 2013-12-09
[28] Beximco Pharma, Bangladesh: Tyclav (http:/ / beximco-pharma. com/ anti-infectives/ 5341-tyclav. html) Linked 2013-12-09
[29] PakMediNet (Pakistan): Zoxicillin (http:/ / www. pakmedinet. com/ trade. php?id=1462) Linked 2013-12-09
[30] Drugs.com: Amoxicillin (http:/ / www.drugs.com/ international/ amoxicillin. html) Linked 2013-12-09
Further reading
Neal, M. J. (2002). Medical pharmacology at a glance (4th ed.). Oxford: Blackwell Science.
ISBN0-632-05244-9.
British National Formulary 45 March 2003
External links
University of Michigan Mott's Children's Hospital article about "amoxicillin rash." (http:/ / www. med. umich.
edu/ 1libr/ pa/ pa_ampirash_hhg. htm)Wikipedia:Link rot (Very similar to Schmitt 2005 content)Wikipedia:Link
rot
U.S. National Library of Medicine: Drug Information Portal - Amoxicillin (http:/ / druginfo. nlm. nih. gov/
drugportal/ dpdirect. jsp?name=Amoxicillin+ anhydrous)
Article Sources and Contributors
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Article Sources and Contributors
Amoxicillin Source: http://en.wikipedia.org/w/index.php?oldid=614008840 Contributors: 213.253.39.xxx, A915, AaronGilliland, Abhishek727, Abm1455, Adambro, Alchaemist, Algebraist,
Allstarecho, AllyUnion, Amcfreely, Anakenabcn, Anastrophe, Anclation, Andres, Anonymous Dissident, Antonycarthy, Anypodetos, Apparition11, Arolga, Ashik031123, AtonX, Avh.on1,
Avono, BacteriaTreatment, Beetstra, Bemoeial, Bender235, Benjah-bmm27, Bluerasberry, Bmramon, Bobbhy01, Bogger, Boing! said Zebedee, BrickBreyer, BrokenSegue, Bryan Derksen,
Bwhack, Can't sleep, clown will eat me, Carl.bunderson, Carlo Banez, Casforty, Cburnett, Chepry, Chowbok, ChrisGualtieri, Cjcollier, CliffC, Constants, Conversion script, CrazyChemGuy,
Crazymonkey1123, Crazynas, DTOx, Dailone, Daisystanton, Daniel,levine, Danny, Davidruben, Deli nk, Derschueler, Desperado28, Divide, Dkapetansky, Doctorcolins, Donmike10,
DragonflySixtyseven, Dreamyshade, Drmies, Drphilharmonic, DuLithgow, Dubaduba, Dyslexic3, Dysmorodrepanis, Earthlyreason, Eccentricity, Echuck215, Eckhart Wrner, Edgar181, Edruc
Limited, Eleassar, Epgui, EtymAesthete, Excirial, F91jsw, Facts707, Faizan, Falcon8765, Fconaway, Fenghan06, FetteK, Flamma, Fraggle81, Frietjes, Funandtrvl, Fuse809, Fvasconcellos,
GadBeebe, Gaius Cornelius, GamblinMonkey, Gary Battle, Gil Gamesh, Gimboid, GorgeCustersSabre, Gothick, GraemeLeggett, Gregfitzy, Guanaco, Gubernator, Gurch, Guy Harris, Guyhoofdt,
Haham hanuka, Hanser, Havaska, Hazard-SJ, HazyM, Hehkuviini, Hu12, Ian Goddard, Insanity Incarnate, Iridescent, J.delanoy, J3ff, JForget, James086, Jandalhandler, Javsav, Jewk, Jfdwolff,
Jhaochen, Jmh649, JohnnyCalifornia, Johnsimilar, Jytdog, J, Kami Shkval, Kc2749, Khoikhoi, Kriegman, Kvn8907, Lenilucho, Leszek Jaczuk, Liberty Miller, Ligand13, LilHelpa, Logan,
Louisajb, M.nelson, Maddiekate, Maderibeyza, Makchem, Malick78, Manderson91, Maximus Rex, Mazin07, Mbartz, Mboverload, Melsit, MightyWarrior, Mimarx, Mind my edits, MindZiper,
MithrandirAgain, Mjp797, Mogism, Morr, MrADHD, Muchie11791, Mygerardromance, Mykhal, Nbauman, Nk, NotWith, Nunh-huh, Nurg, Ohnoitsjamie, Omicronpersei8, P-kun80, Pashihiko,
Pavlemocilac, Pcworld08g, Pharaoh of the Wizards, Philosophistry, Piano non troppo, Pololei, Powertool4, Preslethe, Priestley1628, Qasdfdsaq, R'n'B, R. S. Shaw, Radagast83, Ralmin,
Rangoon11, RavenFeat, Ravenous, Rbaselt, Rd232, Revjmyoung, Rgamble, Rholton, Richard David Ramsey, Rifleman 82, Rjwilmsi, Robert in sacramento, RoseParks, Rotring, SD6-Agent, SLi,
Sajid567, Sburke, SchuminWeb, Shawthorn, Siddhant, Silvermask, SiobhanHansa, Skarebo, Skittleys, Skoch3, Sleske, Smile a While, Snowolf, SpK, Spicemix, Sumeetvingkar, Tarawneh,
Techelf, Terrace4, TexasPharma, Theoregonconnection, Thomas Blomberg, Thricecube, Thumperward, Tiffankim, Tim bates, Tmd63, Tonny1978, Tslocum, Tybalt01, Ugog Nizdast, Ukexpat,
VanillaDeath, Vary, Vawter, Vcohen, Vina, VoxLuna, WDM27, Watermelon mang, Way2veers, WhatamIdoing, Whywhenwhohow, Wikid77, Wright93, Xezbeth, Xiphosurus, Yobol, Yodan,
Zamondothegreat, Zenith Pharmaceuticals Ltd., , 365 anonymous edits
Image Sources, Licenses and Contributors
File:Amoxicillin.svg Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin.svg License: Public Domain Contributors: Ayacop, Fvasconcellos
File:Amoxicillin-3D-balls.png Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin-3D-balls.png License: Public Domain Contributors: Benjah-bmm27, Fvasconcellos, Jynto
File:Yes check.svg Source: http://en.wikipedia.org/w/index.php?title=File:Yes_check.svg License: Public Domain Contributors: Anomie
Image:Amoxicillin.JPG Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin.JPG License: Creative Commons Attribution 3.0 Contributors: Smile a While
Image:Amoxicillin rash 3 hours after 17th dose.JPG Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin_rash_3_hours_after_17th_dose.JPG License: Creative Commons
Attribution-Share Alike Contributors: Skoch3
Image:Amoxicillin rash 11 hours after 17th dose.JPG Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin_rash_11_hours_after_17th_dose.JPG License: Creative Commons
Attribution-Share Alike Contributors: Skoch3
Image:Amoxicillin rash 26 hours after 17th dose.JPG Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin_rash_26_hours_after_17th_dose.JPG License: Creative Commons
Attribution-Share Alike Contributors: Skoch3
File:NOVAMOXIN antibiotic.jpg Source: http://en.wikipedia.org/w/index.php?title=File:NOVAMOXIN_antibiotic.jpg License: Creative Commons Attribution-Sharealike 3.0,2.5,2.0,1.0
Contributors: Original uploader was Bmramon at en.wikipedia
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