U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of AMOXICILLIN ANHYDROUS

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

HIDE SMILES / InChI

Description

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

PubMed

TitleDatePubMed
Adverse reaction to amoxicillin: a case report.
2000 Sep-Oct
Analysis of metronidazole, clarithromycin and tetracycline resistance of Helicobacter pylori isolates from Korea.
2001 Apr
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
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.
2001 Apr
Helicobacter eradication versus prompt endoscopy for dyspepsia.
2001 Apr
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
Simultaneous determination of five beta-lactam antibiotics in bovine milk using liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2001 Apr 1
Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection.
2001 Apr 1
[Eradication therapy of Helicobacter pylori infection].
2001 Feb
[The history of Helicobacter pylori].
2001 Feb
Management of brain stem abscess.
2001 Feb
Cefprozil versus high-dose amoxicillin/clavulanate in children with acute otitis media.
2001 Feb
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.
2001 Feb
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
HMR 3647 human-like treatment of experimental pneumonia due to penicillin-resistant and erythromycin-resistant Streptococcus pneumoniae.
2001 Jan
A multicentre study on eradication of Helicobacter pylori using four 1-week triple therapies in China.
2001 Jan
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
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
Patents

Sample Use Guides

In Vivo Use Guide
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
Name Type Language
AMOXICILLIN ANHYDROUS
HSDB  
Common Name English
AMOXICILLIN [INN]
Common Name English
AMOXYCILLIN
Common Name English
AMOXICILLINE
Common Name English
AMOXICILLIN [MART.]
Common Name English
AMOXICILLIN (ANHYDROUS)
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINO(4-HYDROXYPHENYL)ACETYL)AMINO)-3,3-DIMETHYL-7-OXO-(2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-
Systematic Name English
AMOXICILLIN ANHYDROUS [HSDB]
Common Name English
NSC-277174
Code English
AMOXICILLIN [MI]
Common Name English
(2S,5R,6R)-6-((R)-(-)-2-AMINO-2-(P-HYDROXYPHENYL)ACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
AMOXICILLIN [WHO-DD]
Common Name English
Classification Tree Code System Code
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
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
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
Code System Code Type Description
DRUG BANK
DB01060
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
CAS
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
PRIMARY
EPA CompTox
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
PRIMARY
ChEMBL
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
PRIMARY
INN
3230
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
HSDB
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
PRIMARY
EVMPD
SUB05481MIG
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
NCI_THESAURUS
C87367
Created by admin on Mon Oct 21 22:11:50 UTC 2019 , Edited by admin on Mon Oct 21 22:11:50 UTC 2019
PRIMARY
PUBCHEM
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
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
RXCUI
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
PRIMARY RxNorm
LactMed
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
PRIMARY
ECHA (EC/EINECS)
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
PRIMARY