Amoxicillin  

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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 26787-78-0 ATC code J01CA04 QG51AX01 PubChem 33613 DrugBank APRD00248 ChemSpider 31006 Chemical data Formula C16H19N3O5S  Mol. mass 365.4 g/mol SMILES 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  Y(what is this?)  (verify)

Amoxicillin BP

Amoxicillin (INN), formerly amoxycillin (BAN), abbreviated AMOX, is a moderate-spectrum, bacteriolytic, -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 -lactam antibiotics.

Amoxicillin is susceptible to degradation by -lactamase-producing bacteria, and so may be given with clavulanic acid to decrease its 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 dispersable tablets plus syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration. 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, irritability, volatile mood swings, disorientation, aggressiveness and easy fatigue. Loose bowel movements (diarrhea) also may occur.

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.

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) possibly itchy 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, "amoxicillin-induced morbilliform rash"^[1]). 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. ^[2]

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 spots have grown and begun to merge.

23 hours after first photo. Color apparently fading, much of rash has spread to confluence.

Proprietary preparations

Novamoxin Prescription Drug - 500mg Amoxicillin Trihydrate

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, AMK, Amoksibos, Amoxiclav Sandoz, Amoxidal, Amoxil, Amoxin, Amoksiklav, Amoxibiotic, Amoxicilina, Apo-Amoxi, Augmentin, Bactox, Betalaktam, Cilamox, Curam, Dedoxil, Dispermox, Duomox, E-Mox (250mg and 500 mg), Enhancin, Gimalxina, Geramox, Hiconcil, Isimoxin, Klavox, Lamoxy, Moxatag, Moxilen, Moxypen, Moxyvit, Nobactam, Novamoxin, Ospamox, Panklav, Pamoxicillin, Panamox, Polymox, Samthongcillin, Clamoxyl, Senox, Sinacilin, Trimox, Tolodina, Wymox, Yucla, Zerrsox and Zimox.

References

• Middlebrook Pharmaceuticals (January 2009). "Moxatag - MiddleBrook Pharmaceuticals to Launch Moxatag in March 2009" (html). http://www.middlebrookpharma.com/NEWSROOM_antibiotics/newsdetail.aspx?newsid=1241226. 
• GlaxoSmithKline (February 2006). "Amoxil - Prescribing information" (PDF). http://us.gsk.com/products/assets/us_amoxil.pdf. 
• Neal, M. J. (2002). Medical pharmacology at a glance (4th Ed. 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". Pediatrics 115 (4): 104857. doi:10.1542/peds.2004-1276. PMID 15805383. http://pediatrics.aappublications.org/cgi/content/full/115/4/1048. 
• 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. ed.). New York: Bantam Books. ISBN 0-553-38369-8. 
• British National Formulary 45 March 2003

Footnotes

External links

• University of Michigan Mott's Children's Hospital article about "amoxicillin rash." (Very similar to Schmitt 2005 content)
• Amoxicillin Side Effect Experiences

Recent Amoxicillin Forums  View All  

Allergies To Penicillin can i take amoxicillin if i am allergic to penicillin? Sunday, 9/20/2009 1:52:42 PM  4 Replies

Amox Tr-k Clv TAKE ONE TABLET TWICE A DAY WITH YOGURT, TWO HOURS BEFORE YOUR OTHER MEDICINES. MY QUESTION: WHAT ELSE CAN I TAKE IT WITH BESIDES YOGURT? Wednesday, 7/29/2009 5:59:17 AM  Post a Reply

Amox Tr-k Clv HOW DO I TAKE AMOX TR-K CLV? INSTRUCTIONS TAKE TWO HOURS PRIOR TO OTHER MEDS. TAKE WITH YOGURT. CAN I TAKE IT WITH ANY THING ELSE BESIDES YOGURT? Wednesday, 7/29/2009 5:43:39 AM  Post a Reply

Does This Medicine Contain Gluten? I am a coeliac and have been taking pinaclav for3 days now> I have terrible cramping pains and am worried that these tablets contain some gluten Can anyone help? Friday, 7/3/2009 1:37:08 AM  Post a Reply

Stds On My Thig does this pill have anything to do with treating stds my wifeis had the pill bottel hiden and my pienes is eaching alot Monday, 6/1/2009 9:51:13 AM  1 Reply

Side Effects can wine be used with this drug what are the real side effects and what should Ido Wednesday, 4/22/2009 4:31:38 PM  1 Reply

Do You Chew Or Swallow This Med the pharmacist wasn't very clear on the directions and this is a very large pill so I didn't know if my son could swallow this or not or if I could break it in half it is pink and has rx 763 on the front of it. Saturday, 12/20/2008 1:20:12 PM  1 Reply

11 Year Old Dosage What is the recommended dosage of Amoxicillin for an 11 year old child? Wednesday, 7/2/2008 4:38:27 AM  2 Replies

Dye-free Amoxy Can someone please help me find an 500mg amoxicillin that does not have blue or green dye in the capsule? I would also prefer any amoxicillin capsule that is not red or pink or yellow. I have problems with dyes. It was suggested to me that I call Poison Control and they told me that Duramed makes an amoxicillin that is clear and buff in color - this would be acceptable although, no dye is preferred. Can you get me 500 mg amoxicillin that has no dye or is clear and buff in color? I have a refillable Rx for 200 capsules. Thank you, *S* Thursday, 4/17/2008 12:44:32 PM  3 Replies

Amoxicillin Dosage What is a normal ADULT dosage of amoxicillin for an ear infection? Thursday, 3/20/2008 12:54:51 PM  2 Replies