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C4520

Sigma-Aldrich

Cephalothin sodium salt

Synonym(s):

7-(2-Thienylacetamido)cephalosporanic acid sodium salt, Cephalotin sodium salt

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About This Item

Empirical Formula (Hill Notation):
C16H15N2NaO6S2
CAS Number:
58-71-9
Molecular Weight:
418.42
Beilstein:
4120706
EC Number:
200-394-6
MDL number:
MFCD00072025
UNSPSC Code:
51282506
PubChem Substance ID:
24278314
NACRES:
NA.85

form

crystalline powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

[Na+].CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)Cc3cccs3)C2=O)C([O-])=O

InChI

1S/C16H16N2O6S2.Na/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10;/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23);/q;+1/p-1/t12-,15-;/m1./s1

InChI key

VUFGUVLLDPOSBC-XRZFDKQNSA-M

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General description

Chemical structure: ß-lactam

Application

Cephalothin is a first-generation cephalosporin antibiotic used to study the mechanism of liposome encapsulated antibiotics, strategies for co-opting β-lactamases of Gram-negative bacteria for treatment of antibiotics, and for immunology studies in relation to antibiotics. It is used to study the effect of expression, binding and inhibition of penicillin-binding proteins especially PBP6 on bacterial cell wall mucopeptide synthesis.

Biochem/physiol Actions

Mode of Action: Disrupts the synthesis of the peptidoglycan layer of bacterial cell walls.

Antimicrobial spectrum: Effective aginast both Gram-positive and Gram-negative bacteria.

Mode of Resistance: Production of cephalosporinase will inactivate the product.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry 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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S Mobashery et al.
The Journal of biological chemistry, 261(17), 7879-7887 (1986-06-15)
Two novel C10-(dipeptidyl)cephalosporin esters (3-(beta-chloro-L-alanyl-beta-chloro-L-alanyloxymethyl)-7 beta-(2-thienylacetamido)-3-cephem-4-carboxylic acid (7) and sodium 3-(L-alanyl-L-alanyloxymethyl)-7 beta-(2-thienylacetamido)-3-cephem-4-carboxylate, toluene-sulfonic acid salt (18] were synthesized, and their reactions with Escherichia coli TEM beta-lactamase were examined. Kinetic parameters determined for the enzymatic reactions of 7 (Km = 0.32
Studies on the immune response to penicillin and cephalothin in humans. I. Optimal conditions for titration of hemagglutinating penicillin and cephalothin antibodies.
P Spath et al.
Journal of immunology (Baltimore, Md. : 1950), 107(3), 854-859 (1971-09-01)
Gunnar Baatrup et al.
BMC surgery, 9, 17-17 (2009-12-09)
The antibiotics used for prophylaxis during surgery may influence the rate of surgical site infections. Tetracyclines are attractive having a long half-life and few side effects when used in a single dose regimen. We studied the rate of surgical site
Esteban C Nannini et al.
Antimicrobial agents and chemotherapy, 54(5), 2206-2208 (2010-03-10)
Using 98 clinical methicillin-susceptible Staphylococcus aureus isolates of known beta-lactamase (Bla) type, we found a pronounced inoculum effect for cephalexin (mostly Bla type A and C strains), a mild inoculum effect for cephalothin (especially types B and C), and no
Sarah M Drawz et al.
Protein science : a publication of the Protein Society, 20(6), 941-958 (2011-03-16)
In Pseudomonas aeruginosa, the chromosomally encoded class C cephalosporinase (AmpC β-lactamase) is often responsible for high-level resistance to β-lactam antibiotics. Despite years of study of these important β-lactamases, knowledge regarding how amino acid sequence dictates function of the AmpC Pseudomonas-derived
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