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A8523

Sigma-Aldrich

Amoxicillin

95.0-102.0% anhydrous basis

Synonym(s):

Amoxicillin anhydrous, D-(-)-α-Amino-p-hydroxybenzyl penicillin

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About This Item

Empirical Formula (Hill Notation):
C16H19N3O5S
CAS Number:
26787-78-0
Molecular Weight:
365.40
Beilstein:
7507120
EC Number:
248-003-8
MDL number:
MFCD00056860
UNSPSC Code:
51101500
PubChem Substance ID:
329770960
NACRES:
NA.85

Quality Level

200

Assay

95.0-102.0% anhydrous basis

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(O)=O

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

InChI key

LSQZJLSUYDQPKJ-NJBDSQKTSA-N

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General description

Chemical structure: ß-lactam

Application

Amoxicillin is used to study the oxygen dependent antimicrobial systems of polymorphonuclear leukocytes (PMNLs), the risk of resistance development in Helicobacter pylori, and various dosing strategies against Streptococcus pneumoniae and Pneumococcal pneumonia . It is also used to study the synthesis of bacterial cell walls at the level of peptidoglycan polymer chain cross-linking involving bacterial transpeptidase.

Biochem/physiol Actions

Amoxicillin is a broad-spectrum, β-lactam antibiotic. It is a 4-hydroxy analog of ampicillin with similar ranges of actions and utility to ampicillin. Amoxicillin inhibits the cross-linkage between linear peptidoglycan polymer chains that are the major component of both Gram-positive and Gram-negative bacteria.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Sörberg et al.
Antimicrobial agents and chemotherapy, 42(5), 1222-1228 (1998-05-21)
We have studied initial killing, morphological alterations, the frequency of occurrence, and the selective growth of resistant subpopulations of Helicobacter pylori during exposure to amoxicillin, clarithromycin, or metronidazole by bioluminescence assay of intracellular ATP levels, microscopy, and a viable count
Jose-Manuel Rodriguez-Martinez et al.
Antimicrobial agents and chemotherapy, 54(1), 471-476 (2009-11-18)
Two carbapenem-resistant isolates, one Escherichia coli isolate and one Klebsiella pneumoniae isolate, recovered from an Algerian patient expressed a novel VIM-type metallo-beta-lactamase (MBL). The identified bla(VIM-19) gene was located on a ca. 160-kb plasmid and located inside a class 1
Raymond Cha et al.
The Journal of antimicrobial chemotherapy, 54(6), 1067-1071 (2004-10-16)
Beta-Lactam antimicrobials are dosed intermittently or continuously based on their short half-lives and concentration-independent activity. Based on the relationship between antimicrobial killing and bacterial growth cycle, the pharmacodynamics of a unique pulsatile strategy was investigated. In vitro pharmacodynamic models with
Thierry Naas et al.
Antimicrobial agents and chemotherapy, 52(4), 1257-1263 (2008-01-30)
Genetic structures surrounding the carbapenem-hydrolyzing Ambler class A bla KPC gene were characterized in several KPC-positive Klebsiella pneumoniae and Pseudomonas aeruginosa strains isolated from the United States, Colombia, and Greece. The bla KPC genes were associated in all cases with
Amélie Carrër et al.
Antimicrobial agents and chemotherapy, 54(3), 1369-1373 (2010-01-21)
Eighteen carbapenem-resistant, OXA-48-positive enterobacterial isolates recovered from Turkey, Lebanon, Egypt, France, and Belgium were analyzed. In most isolates, similar 70-kb plasmids carrying the carbapenemase gene bla(OXA-48) were identified. That gene was located within either transposon Tn1999 or transposon Tn1999.2, which
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