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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:
51102829
PubChem Substance ID:
329770960
NACRES:
NA.85

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

Storage Class Code

11 - Combustible Solids

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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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
Yohei Doi et al.
Antimicrobial agents and chemotherapy, 52(6), 1952-1956 (2008-03-26)
A chromosomally encoded class D beta-lactamase, OXA-114, was characterized from Achromobacter xylosoxidans strain CIP69598. beta-Lactamase OXA-114 shared 56% amino acid identity with the naturally occurring class D beta-lactamase of Burkholderia cenocepacia and 42% identity with the acquired oxacillinases OXA-9 and
José-Manuel Rodríguez-Martínez et al.
Antimicrobial agents and chemotherapy, 53(5), 1766-1771 (2009-03-05)
The characterization of AmpC-type beta-lactamases was performed in a collection of 32 clinical Pseudomonas aeruginosa isolates with intermediate susceptibility or resistance to imipenem and ceftazidime. Twenty-one out of those 32 isolates overexpressed AmpC beta-lactamase, and the MICs of ceftazidime and
Heather K Sun et al.
The Journal of antimicrobial chemotherapy, 56(3), 559-565 (2005-07-19)
Amoxicillin and clarithromycin have been proven to be effective in the treatment of community-acquired pneumonia. This study investigated the in vivo bactericidal efficacy of a novel, pulsatile dosing strategy for amoxicillin and clarithromycin, when used as monotherapy and combination therapy.
Laurent Poirel et al.
Antimicrobial agents and chemotherapy, 54(11), 4914-4916 (2010-09-09)
A multidrug-resistant Escherichia coli isolate recovered in Australia produced a carbapenem-hydrolyzing β-lactamase. Molecular investigations revealed the first identification of the bla(NDM-1) metallo-β-lactamase gene in that country. In addition, this E. coli isolate expressed the extended-spectrum β-lactamase CTX-M-15, together with two
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