Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H19N3O5S |
| Molecular Weight | 365.404 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(O)=O
InChI
InChIKey=LSQZJLSUYDQPKJ-NJBDSQKTSA-N
InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
Amoxicillin is one of the widely prescribed antibacterial agents, which was discovered by scientists at Beecham Research Laboratories in 1972. In the US GlaxoSmithKline markets it under the original brand name Amoxil. It is the first line treatment for middle ear infections. It is also used for strep throat, pneumonia, skin infections, and urinary tract infections it is taken by mouth. Amoxicillin inhibits the third and final stage of bacterial cell wall synthesis by preferentially binding to specific penicillin-binding proteins (PBPs) that are located inside the bacterial cell wall. This results in a formation of defective cell wall and a cell death. Common side effects include nausea and rash. It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea. It should not be used in those who are allergic to penicillin.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Adverse reaction to amoxicillin: a case report. | 2000 Sep-Oct |
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| Analysis of metronidazole, clarithromycin and tetracycline resistance of Helicobacter pylori isolates from Korea. | 2001 Apr |
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| Efficacy, safety and tolerability of 3 day azithromycin versus 10 day co-amoxiclav in the treatment of children with acute lower respiratory tract infections. | 2001 Apr |
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| Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue. | 2001 Apr |
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| Helicobacter eradication versus prompt endoscopy for dyspepsia. | 2001 Apr |
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| Effect of the treatment of Helicobacter pylori infection on gastric emptying and its influence on the glycaemic control in type 1 diabetes mellitus. | 2001 Apr |
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| Simultaneous determination of five beta-lactam antibiotics in bovine milk using liquid chromatography coupled with electrospray ionization tandem mass spectrometry. | 2001 Apr 1 |
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| Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection. | 2001 Apr 1 |
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| [Eradication therapy of Helicobacter pylori infection]. | 2001 Feb |
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| [The history of Helicobacter pylori]. | 2001 Feb |
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| Management of brain stem abscess. | 2001 Feb |
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| Cefprozil versus high-dose amoxicillin/clavulanate in children with acute otitis media. | 2001 Feb |
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| Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis. | 2001 Feb |
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| The effect of postsurgical antibiotics on the healing of intrabony defects following treatment with enamel matrix proteins. | 2001 Feb |
|
| Bioequivalence study of a novel Solutab tablet formulation of amoxicillin/clavulanic acid versus the originator film-coated tablet. | 2001 Feb |
|
| Sensitivity of Borrelia burgdorferi strains isolated in the Czech Republic. | 2001 Feb |
|
| Do some patients with Helicobacter pylori infection benefit from an extension to 2 weeks of a proton pump inhibitor-based triple eradication therapy? | 2001 Feb |
|
| Comparison of the efficacy and safety of different formulations of omeprazole-based triple therapies in the treatment of Helicobacter pylori-positive peptic ulcer. | 2001 Feb |
|
| Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication. | 2001 Feb |
|
| Managing pneumonia in general practice. | 2001 Feb |
|
| [Mechanism of drug resistance in Helicobacter pylori]. | 2001 Feb |
|
| [A strategy for second-line anti-Helicobacter pylori therapy in patients with previously failed treatment]. | 2001 Feb |
|
| [Usefulness of new triple therapy containing PPI]. | 2001 Feb |
|
| [Selection of antibiotics and planning of eradication for H. pylori infection]. | 2001 Feb |
|
| [Recent guidelines for the management of Helicobacter pylori infection]. | 2001 Feb |
|
| Topical antibiotic prophylaxis for bacteremia after dental extractions. | 2001 Feb |
|
| [Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege]. | 2001 Jan |
|
| [Pneumococcal antibiotic resistance in 1999. Results from 19 registries for 1999]. | 2001 Jan |
|
| [Prevention of endocarditis within the scope of ENT interventions. Current recommendations]. | 2001 Jan |
|
| [Dilated cardiomyopathy and panuveitis as presenting symptoms of Lyme disease. General review of one case]. | 2001 Jan |
|
| High amoxycillin resistance in Helicobacter pylori isolated from gastritis and peptic ulcer patients in western Nigeria. | 2001 Jan |
|
| Compliance issues related to the selection of antibiotic suspensions for children. | 2001 Jan |
|
| Oral moxifloxacin vs high-dosage amoxicillin in the treatment of mild-to-moderate, community-acquired, suspected pneumococcal pneumonia in adults. | 2001 Jan |
|
| Randomized, double-blind, double-dummy study comparing the efficacy and safety of amoxycillin 1 g bd with amoxycillin 500 mg tds in the treatment of acute exacerbations of chronic bronchitis. | 2001 Jan |
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| HMR 3647 human-like treatment of experimental pneumonia due to penicillin-resistant and erythromycin-resistant Streptococcus pneumoniae. | 2001 Jan |
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| A multicentre study on eradication of Helicobacter pylori using four 1-week triple therapies in China. | 2001 Jan |
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| Neonatal group B streptococcal infection. Results of 33 months of universal maternal screening and antibioprophylaxis. | 2001 Jan |
|
| Cause of high variability in drug dissolution testing and its impact on setting tolerances. | 2001 Jan |
|
| Charm Safe-Level beta-Lactam Test for amoxicillin, ampicillin, ceftiofur, cephapirin, and penicillin G in raw commingled milk. | 2001 Jan-Feb |
|
| Clinical onset of the Crohn's disease after eradication therapy of Helicobacter pylori infection. Does Helicobacter pylori infection interact with natural history of inflammatory bowel diseases? | 2001 Jan-Feb |
|
| [A prospective study on erysipelas and infectious cellulitis: how are they dealt within hospital?]. | 2001 Mar |
|
| Peptic ulcer occurrence in follow-up of chronic gastritis in patients with treated and not eradicated CagA-positive Helicobacter pylori infection. | 2001 Mar |
|
| The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication. | 2001 Mar |
|
| A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication. | 2001 Mar |
|
| Five-day proton pump inhibitor-based quadruple therapy regimen is more effective than 7-day triple therapy regimen for Helicobacter pylori infection. | 2001 Mar |
|
| Broad-spectrum antibiotics for spontaneous preterm labour: the ORACLE II randomised trial. ORACLE Collaborative Group. | 2001 Mar 31 |
|
| Broad-spectrum antibiotics for preterm, prelabour rupture of fetal membranes: the ORACLE I randomised trial. ORACLE Collaborative Group. | 2001 Mar 31 |
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| Antibiotic resistance and antibiotic sensitivity based treatment in Helicobacter pylori infection: advantages and outcome. | 2001 May |
|
| Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999. | 2001 May 15 |
|
| Prospective evaluation of the impact of amoxicillin, clarithromycin and their combination on human gastrointestinal colonization by Candida species. | 2001 May-Jun |
Sample Use Guides
In adults, 750-1750 mg/day in divided doses every 8-12 hours. In Pediatric Patients > 3 Months of Age, 20-45 mg/kg/day in divided doses every 8-12 hours. Treatment of gonorrhea is 3 grams as a single oral dose. The upper dose for neonates and infants ≤ 3 months is 30 mg/kg/day divided every 12 hours. Dosing for H. pylori Infection: Triple therapy: 1 gram AMOXIL, 500 mg clarithromycin, and 30 mg lansoprazole, all given twice daily (every 12 hours) for 14 days. Dual therapy: 1 gram AMOXIL and 30 mg lansoprazole, each given three times daily (every 8 hours) for 14 days.
Route of Administration:
Oral
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|---|---|---|---|---|
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NDF-RT |
N0000175497
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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NCI_THESAURUS |
C1500
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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WHO-ATC |
J01CA04
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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| Code System | Code | Type | Description | ||
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DB01060
Created by
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PRIMARY | |||
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26787-78-0
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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PRIMARY | |||
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26787-78-0
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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PRIMARY | |||
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CHEMBL1082
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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PRIMARY | |||
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3230
Created by
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PRIMARY | |||
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26787-78-0
Created by
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PRIMARY | |||
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SUB05481MIG
Created by
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PRIMARY | |||
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C87367
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33613
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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PRIMARY | |||
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M1844
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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PRIMARY | Merck Index | ||
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1297882
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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26787-78-0
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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248-003-8
Created by
admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
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PRIMARY |
ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
