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-

2-carboxylic acid
Identifiers

CAS number [1]

26787-78-0

ATC code [2] [3]

J01 CA04 QG51 AX01

PubChem [4]
CID 33613

DrugBank [5]
DB01060

ChemSpider [6]
31006

Chemical data

Formula C16H19N3O5S

Mol. mass 365.4 g/mol

SMILES [7] [8]

eMolecules & PubChem

Pharmacokinetic data

Bioavailability 95% oral

Metabolism less than 30% biotransformed in liver

Half-life 61.3 minutes

Excretion renal

Therapeutic considerations

Pregnancy cat. A(AU) B(US)

Legal status POM (UK)

Routes Oral, intravenous

[9]
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Amoxicillin 2

Amoxicillin (INN), formerly amoxycillin (BAN), amoxycillin

(cilamox) in Australia[10] , 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.[11]

Amoxicillin is susceptible to degradation by β-lactamase-producing

bacteria, and so may be given with clavulanic acid to decrease its
Amoxicillin BP
susceptibility.

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[12] ). 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, suicidal thoughts, depression, 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.[13] [14]
Amoxicillin 3

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 [15][16],
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"[17] ). 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.[18]

Non-allergic amoxicillin rash 8
days after first dose, 24 hours
after rash began. Diagnosed by
pediatric resident at local
university hospital.
8 hours after first photo. Individual 23 hours after first photo. Color apparently
spots have grown and begun to fading, much of rash has spread to
merge. confluence.

Proprietary preparations
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, Novamoxin Prescription Drug - 500mg
Amoxicillin Trihydrate
Panklav, Pamoxicillin, Panamox, Polymox, Samthongcillin, Clamoxyl,
Senox, Sinacilin, Trimox, Tolodina, Tormoxin (India), Wymox, Yucla,
Zerrsox and Zimox.
Amoxicillin 4

References
• Middlebrook Pharmaceuticals (March 2009). "MiddleBrook Pharmaceuticals Launches MOXATAG(TM), the
First and Only FDA-Approved Once-Daily Amoxicillin" [19].
• GlaxoSmithKline (February 2006). "Amoxil - Prescribing information" [20] (PDF).
• Neal, M. J. (2002). Medical pharmacology at a glance (4th ed.). Oxford: Blackwell Science.
ISBN 0-632-05244-9.
• Pichichero ME (April 2005). "A review of evidence supporting the American Academy of Pediatrics
recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients" [21]. Pediatrics 115 (4):
1048–57. doi:10.1542/peds.2004-1276. PMID 15805383.
• 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

External links
• University of Michigan Mott's Children's Hospital article about "amoxicillin rash." [22] (Very similar to Schmitt
2005 content)
• Amoxicillin Side Effect Experiences [23]
• U.S. National Library of Medicine: Drug Information Portal - Amoxicillin [24]

References
[1] http:/ / www. nlm. nih. gov/ cgi/ mesh/ 2009/ MB_cgi?term=26787-78-0& rn=1
[2] http:/ / www. whocc. no/ atc_ddd_index/ ?code=J01CA04
[3] http:/ / www. whocc. no/ atcvet/ atcvet_index/ ?code=QG51AX01
[4] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=33613
[5] http:/ / www. drugbank. ca/ cgi-bin/ show_drug. cgi?CARD=DB01060
[6] http:/ / www. chemspider. com/ Chemical-Structure. 31006
[7] http:/ / www. emolecules. com/ cgi-bin/ search?t=ex&
q=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%29cc1%
[8] http:/ / pubchem. ncbi. nlm. nih. gov/ search/
?smarts=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccc%28O%2
[9] http:/ / en. wikipedia. org/ w/ index. php?& diff=cur& oldid=321803860
[10] (http:/ / www. racgp. org. au/ cmi/ txcamoxc. pdf), Royal Australian College of General Practitioners Leaflet.
[11] "Adolescent Acne: Management" (http:/ / www. medscape. com/ viewarticle/ 430534_5). .
[12] www.UpToDate.com
[13] Cundiff J, Joe S. Amoxicillin-clavulanic acid-induced hepatitis. Amer. J. Otolaryngol. 28: 28-30, 2007.
[14] R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 81-83.
[15] http:/ / forums. wrongdiagnosis. com/ showthread. php?t=15875
[16] http:/ / www. medhelp. org/ posts/ Allergy/ Rash-from-Amoxicillin/ show/ 4008
[17] e.g. Role of delayed cellular hypersensitivity and adhesion molecules in amoxicillin-induced morbilliform rashes (http:/ / cat. inist. fr/
?aModele=afficheN& cpsidt=2654598)
[18] Kagan, B (1977). "Ampicillin rash" (http:/ / www. pubmedcentral. nih. gov/ articlerender. fcgi?artid=1237570). Western Journal of
Medicine 126 (4): 333–335. PMID 855325. PMC 1237570. .
[19] http:/ / www. middlebrookpharma. com/ releasedetail. cfm?ReleaseID=427462
[20] http:/ / us. gsk. com/ products/ assets/ us_amoxil. pdf
[21] http:/ / pediatrics. aappublications. org/ cgi/ content/ full/ 115/ 4/ 1048
[22] http:/ / www. med. umich. edu/ 1libr/ pa/ pa_ampirash_hhg. htm
[23] http:/ / www. amoxicillinsideeffects. net/
[24] http:/ / druginfo. nlm. nih. gov/ drugportal/ dpdirect. jsp?name=Amoxicillin+ anhydrous
Article Sources and Contributors 5

Article Sources and Contributors

Amoxicillin  Source: http://en.wikipedia.org/w/index.php?oldid=382655420  Contributors: 213.253.39.xxx, Abhishek727, Adambro, Alchaemist, Algebraist, Allstarecho, AllyUnion, Amcfreely,
Anakenabcn, Anastrophe, Anclation, Anonymous Dissident, Anypodetos, AtonX, Avono, Beetstra, Bemoeial, Benjah-bmm27, Bmramon, Bobbhy01, Boing! said Zebedee, BrickBreyer,
BrokenSegue, Bryan Derksen, Bwhack, Can't sleep, clown will eat me, Carl.bunderson, Carlo Banez, Casforty, Cburnett, Chepry, Chowbok, Cjcollier, Constants, Conversion script,
CrazyChemGuy, Crazynas, DTOx, Dailone, Daisystanton, Daniel,levine, Danny, Davidruben, Desperado28, Divide, Dreamyshade, Drphilharmonic, DuLithgow, Dubaduba, Dyslexic3,
Dysmorodrepanis, Earthlyreason, Echuck215, Eckhart Wörner, Edruc Limited, Eleassar, Excirial, Facts707, Falcon8765, Fenghan06, Flamma, Fvasconcellos, Gaius Cornelius, GamblinMonkey,
Gil Gamesh, Gimboid, GorgeCustersSabre, Gothick, GraemeLeggett, Gregfitzy, Guanaco, Gubernator, Gurch, Guy Harris, Haham hanuka, Hanser, Havaska, Hazard-SJ, HazyM, Hehkuviini, Ian
Goddard, Insanity Incarnate, Iridescent, J.delanoy, J3ff, JForget, Javsav, Jfdwolff, Jhaochen, Kami Shkval, Khoikhoi, Kvn8907, Lenilucho, Leszek Jańczuk, Liberty Miller, Ligand13, LilHelpa,
Literaturegeek, Maddiekate, Maderibeyza, Maximus Rex, Mazin07, Mboverload, Melsit, MightyWarrior, Mimarx, MithrandirAgain, Mjp797, Morr, Muchie11791, Mygerardromance, Mykhal,
Nk, Nunh-huh, Ohnoitsjamie, Omicronpersei8, P-kun80, Pcworld08g, Pharaoh of the Wizards, Philosophistry, Piano non troppo, Powertool4, Priestley1628, R. S. Shaw, Radagast83, Ralmin,
RavenFeat, Ravenous, Rbaselt, Rd232, Revjmyoung, Rgamble, Rholton, Rifleman 82, Rjwilmsi, Robert in sacramento, RoseParks, Rotring, SD6-Agent, SLi, Shawthorn, Siddhant, Silvermask,
SiobhanHansa, Skarebo, Skittleys, Skoch3, Smile a While, Snowolf, SpK, Sumeetvingkar, Tarawneh, Techelf, Terrace4, TexasPharma, Thricecube, Thumperward, Tim bates, Tmd63, Tslocum,
Tybalt01, Ukexpat, Vary, Vina, VoxLuna, WDM27, WhatamIdoing, Wright93, Xezbeth, Xiphosurus, Yodan, Zamondothegreat, ‫طبلا يلع نسح‬, 251 anonymous edits

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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, Ephemeronium
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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: GNU Free
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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: GNU Free
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