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Key Documents

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C4895

Sigma-Aldrich

Cephalexin hydrate

first-generation cephalosporin antibiotic

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About This Item

Fórmula empírica (notación de Hill):
C16H17N3O4S · xH2O
Número de CAS:
1820673-23-1
Peso molecular:
347.39 (anhydrous basis)
Beilstein/REAXYS Number:
965503
EC Number:
239-773-6
MDL number:
MFCD00056877
UNSPSC Code:
51282503
PubChem Substance ID:
24278316
NACRES:
NA.85

Quality Level

200

form

powder

pKa 

5.2
7.3

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

InChI

1S/C16H17N3O4S.H2O/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9;/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23);1H2/t10-,11-,15?;/m1./s1

InChI key

AVGYWQBCYZHHPN-FNOHQHCYSA-N

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General description

Chemical structure: ß-lactam

Application

Cephalexin is a cephalosporin antibiotic used to study the effect of expression, binding, and inhibition of PBP3 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis.

Biochem/physiol Actions

Cephalexin disrupts the synthesis of the peptidoglycan layer of bacterial cell walls which is responsible for cell wall structural integrity. Peptidoglycan synthesis is facilitated by transpeptidases known as penicillin-binding proteins (PBPs). PBPs bind to the D-Ala-D-Ala at the end of muropeptides (peptidoglycan precursors) to crosslink the peptidoglycan. Cephalexin antibiotics mimic the D-Ala-D-Ala site, thereby competitively inhibiting PBP crosslinking of peptidoglycan.

Other Notes

Storage of this product should be in airtight containers and protected from light.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificados de análisis (COA)

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Alexander Perniss et al.
Scientific reports, 8(1), 5681-5681 (2018-04-11)
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Hiroshi Kodaira et al.
The Journal of pharmacology and experimental therapeutics, 339(3), 935-944 (2011-09-22)
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Tomoko Sugiura et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(6), 1181-1188 (2008-03-07)
Gastrointestinal (GI) absorption of certain therapeutic agents is thought to be mediated by solute carrier (SLC) transporters, although minimal in vivo evidence has been reported. Here, we show key roles of postsynaptic density 95/disk-large/ZO-1 (PDZ) domain-containing protein, PDZK1, as a
Steven D Coon et al.
American journal of physiology. Gastrointestinal and liver physiology, 305(10), G678-G684 (2013-09-28)
Glucose-dependent insulinotropic polypeptide (GIP) secreted from jejunal mucosal K cells augments insulin secretion and plays a critical role in the pathogenesis of obesity and Type 2 diabetes mellitus. In recent studies, we have shown GIP directly activates Na-glucose cotransporter-1 (SGLT1)
William T Gray et al.
Cell, 177(6), 1632-1648 (2019-06-01)
The scaling of organelles with cell size is thought to be exclusive to eukaryotes. Here, we demonstrate that similar scaling relationships hold for the bacterial nucleoid. Despite the absence of a nuclear membrane, nucleoid size strongly correlates with cell size
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