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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/REAXYS Number:
4120706
EC Number:
200-394-6
MDL number:
MFCD00072025
UNSPSC Code:
51101500
PubChem Substance ID:
24278314
NACRES:
NA.85

form

crystalline powder

Quality Level

200

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

signalword

Danger

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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)
J V Desiderio et al.
The Journal of infectious diseases, 148(3), 563-570 (1983-09-01)
Multilamellar liposomes (lipid bilayer vesicles) composed of phosphatidylcholine, cholesterol, and phosphatidylserine (molar ratio, 6:3:1) were produced and then made to entrap an aqueous solution of cephalothin. Resident murine peritoneal macrophages were shown to be capable of interiorizing the liposome-antibiotic complex;
Bulent Tokgoz et al.
Renal failure, 32(2), 179-184 (2010-03-05)
Aminoglycosides have been used in the treatment of CAPD peritonitis despite their potential risk for ototoxicity. The ototoxicity risk of intraperitoneally administered aminoglycosides has been investigated by a number of studies. However, their results are somewhat conflicting. The aim of
Smriti Sharma et al.
Journal of molecular modeling, 18(2), 481-492 (2011-05-05)
β-Lactamases are bacterial enzymes that act as a bacterial defense system against β-lactam antibiotics. β-Lactamase cleaves the β-lactam ring of the antibiotic by a two step mechanism involving acylation and deacylation steps. Although class C β-lactamases have been investigated extensively
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