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-carboxylicacid

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 C16H19N3O5S

Mol. mass 365.4 g/mol

 (what is this?)   (verify) [13]

Amoxicillin BP

Amoxicillin (INN, BAN), or amoxycillin (AAN), and abbreviatedamox, is an antibiotic useful for the treatment of a number of bacterialinfections.

It is a moderate-spectrum, bacteriolytic, β-lactam antibiotic in theaminopenicillin family used to treat susceptible Gram-positive andGram-negative bacteria. It is usually the drug of choice within the classbecause it is better-absorbed, following oral administration, than otherβ-lactam antibiotics.

Amoxicillin is susceptible to degradation by β-lactamase-producingbacteria, which are resistant to a narrow spectrum of β-lactamantibiotics, such as penicillin. For this reason, it is often combined with clavulanic acid, a β-lactamase inhibitor. Thisincreases effectiveness by reducing its susceptibility to β-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 neededin a basic health system.

Medical usesAmoxicillin is used in the treatment of a number of infections, including acute otitis media, streptococcalpharyngitis, pneumonia, skin infections, urinary tract infections, Salmonella infections, Lyme disease, and chlamydiainfections. It is also used to prevent bacterial endocarditis in high-risk people having dental work done, to preventStreptococcus pneumoniae and other encapsulated bacterial infections in those without spleens, such as people withsickle-cell disease, and for both the prevention and the treatment of anthrax. The United Kingdom recommendsagainst its use for infectious endocarditis prophylaxis. These recommendations have not appeared to have changedthe rates of infection for infectious endocarditis.Amoxicillin and amoxicillin-clavulanate are recommended by guidelines as the first-choice drug for bacterialsinusitis, 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 effectivetreatment for cases of acne vulgaris that have responded poorly to other antibiotics, such as doxycycline andminocycline.

Amoxicillin 3

Adverse effectsSide-effects are similar to those for other beta-lactam antibiotics, including nausea, vomiting, rashes, andantibiotic-associated colitis. Loose bowel movements (diarrhea) may also occur. Rarer side-effects include mentalchanges, 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 besought as quickly as possible. The initial phase of such a reaction often starts with a change in mental state, skin rashwith intense itching (often beginning in fingertips and around groin area and rapidly spreading), and sensations offever, 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 weekafter 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 somepatients. Young children having ingested acute overdoses of amoxicillin-manifested lethargy, vomiting, and renaldysfunction.

Nonallergic amoxicillin rashBetween 3 and 10% of children taking amoxicillin (or ampicillin) show a late-developing (>72 hours after beginningmedication 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 bea true allergic reaction, and is not a contraindication for future amoxicillin usage, nor should the current regimennecessarily be stopped. However, this common amoxicillin rash and a dangerous allergic reaction cannot easily bedistinguished 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 about80-90% of patients with acute Epstein Barr virus infection treated with amoxicillin or ampicillin develop such a rash.

Nonallergic amoxicillin rasheight 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 appearsto be fading, and much of rash has spread to

confluence.

Amoxicillin 4

InteractionAmoxicillin 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 actionMain article: Beta-lactam antibioticThis drug acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linearpeptidoglycan polymer chains that make up a major component of the cell walls of both Gram-positive andGram-negative bacteria.It has two ionizable groups in the physiological range (the amino group in alpha-position to the amide carbonylgroup and the carboxyl group).

Spectrum of microorganism susceptibility and resistanceIn general, Streptococcus, Bacillus subtilis, Enterococcus, Haemophilus, Helicobacter, and Moraxella aresusceptible 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.

HistorySee also: Timeline of antibioticsAmoxicillin was one of several semisynthetic derivatives of 6-aminopenicillanic acid (6-APA) developed atBeecham in the 1960s. It became available in 1972, and was the second aminopenicillin to reach the market (afterampicillin in 1961).[15] Co-amoxiclav became available in 1981.

Formulations

Modes of deliveryPharmaceutical manufacturers make amoxicillin in trihydrate form, available as capsules, chewable and dispersibletablets, 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 totake tablets or capsules.Research with mice indicated successful delivery using intraperitoneally injected amoxicillin-bearing microparticles.

Amoxicillin 5

Brand names

Novamoxin prescription drug—500mgAmoxicillin trihydrate

Amoxicillin is one of the semisynthetic penicillins discovered byBeecham scientists. The patent for amoxicillin has expired, thusamoxicillin and co-amoxiclav preparations are marketed under manytrade 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 7

[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.

ISBN 0-632-05244-9.• 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:Linkrot

• 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 8

Article Sources and ContributorsAmoxicillin  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 Wörner, Edgar181, EdrucLimited, 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, Jü, Kami Shkval, Kc2749, Khoikhoi, Kriegman, Kvn8907, Lenilucho, Leszek Jańczuk, 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 ,حسن علي البط anonymous edits

Image Sources, Licenses and ContributorsFile:Amoxicillin.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin.svg  License: Public Domain  Contributors: Ayacop, FvasconcellosFile: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, JyntoFile:Yes check.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Yes_check.svg  License: Public Domain  Contributors: AnomieImage:Amoxicillin.JPG  Source: http://en.wikipedia.org/w/index.php?title=File:Amoxicillin.JPG  License: Creative Commons Attribution 3.0  Contributors: Smile a WhileImage: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 CommonsAttribution-Share Alike  Contributors: Skoch3Image: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 CommonsAttribution-Share Alike  Contributors: Skoch3Image: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 CommonsAttribution-Share Alike  Contributors: Skoch3File: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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