C7912

Sigma-Aldrich

Cefotaxime sodium salt

potency: 916-964 μg per mg

Synonym(s):
Cefotaxim sodium salt
Empirical Formula (Hill Notation):
C16H16N5NaO7S2
CAS Number:
Molecular Weight:
477.45
Beilstein/REAXYS Number:
5711411
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

form

powder

Quality Level

potency

916-964 μg per mg

solubility

H2O: 50 mg/mL

Mode of action

cell wall synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

storage temp.

2-8°C

SMILES string

[Na+].[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\c3csc(N)n3)C([O-])=O

InChI

1S/C16H17N5O7S2.Na/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8;/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26);/q;+1/p-1/b20-9-;/t10-,14-;/m1./s1

InChI key

AZZMGZXNTDTSME-JUZDKLSSSA-M

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Related Categories

General description

Chemical structure: ß-lactam

Application

Cefotaxim has been used to find new residues involved in cefotaxime hydrolysis in CTX-M β-lactamases, to study antibiotic-susceptible and -resistant Streptococcus pneumoniae infections, and to study pneumococcal pneumonia and the pharmokinetics of various treatments. It may be used to study the effects of binding and inhibition of penicillin binding protein 2 (PBP2) on bacterial mucopeptide synthesis.

Biochem/physiol Actions

Cefotaxim inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs) which inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls. As a result, bacteria lyse due to cell wall autolytic enzymes.

Other Notes

Broad spectrum third generation cephalosporin antibiotic.
Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Francisco José Pérez-Llarena et al.
Antimicrobial agents and chemotherapy, 55(9), 4361-4368 (2011-07-07)
The CTX-M β-lactamases are an increasingly prevalent group of extended-spectrum β-lactamases (ESBL). Point mutations in CTX-M β-lactamases are considered critical for enhanced hydrolysis of cefotaxime. In order to clarify the structural determinants of the activity against cefotaxime in CTX-M β-lactamases...
Violeta Rodríguez-Cerrato et al.
The Journal of antimicrobial chemotherapy, 60(5), 1159-1162 (2007-09-11)
In an innovative therapeutic exploitation against antibiotic-resistant Streptococcus pneumoniae, here we have evaluated the in vitro activity of a purified bacterially-encoded cell wall lytic enzyme, LytA (the major pneumococcal autolysin), and compared it with those of Cpl-1 and Pal (pneumococcal...
F Soriano et al.
The Journal of antimicrobial chemotherapy, 38(2), 227-236 (1996-08-01)
In an attempt to determine the susceptibility breakpoints for amoxycillin, co-amoxiclav and cefotaxime in pneumococcal pneumonia, a neutropenic mouse model was established and tested with two strains having different susceptibility to penicillins and cefotaxime. With a penicillin-sensitive strain (MIC/MBC =...
Yidan Cui et al.
PloS one, 7(11), e48880-e48880 (2012-11-16)
Extended-spectrum β-lactamase (ESBL)-producing Enterobacteriaceae poses serious challenges to clinicians because of its resistance to many classes of antibiotics. The mechanism of synergistic activity of a combination of (-)-epigallocatechin-3-gallate (EGCG) and β-lactam antibiotics cefotaxime was studied on Extended-spectrum β-lactamase producing Escherichia...
Martijn F Schenk et al.
PLoS genetics, 8(6), e1002783-e1002783 (2012-07-05)
For a quantitative understanding of the process of adaptation, we need to understand its "raw material," that is, the frequency and fitness effects of beneficial mutations. At present, most empirical evidence suggests an exponential distribution of fitness effects of beneficial...

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