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C4895

Sigma-Aldrich

Cephalexin hydrate

first-generation cephalosporin antibiotic

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About This Item

Empirical Formula (Hill Notation):
C16H17N3O4S · xH2O
CAS Number:
1820673-23-1
Molecular Weight:
347.39 (anhydrous basis)
Beilstein:
965503
EC Number:
239-773-6
MDL number:
MFCD00056877
UNSPSC Code:
51282503
PubChem Substance ID:
24278316
NACRES:
NA.85

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

Signal Word

Danger

Hazard Statements

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Alexander Perniss et al.
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The Journal of pharmacology and experimental therapeutics, 339(3), 935-944 (2011-09-22)
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Steven D Coon et al.
American journal of physiology. Gastrointestinal and liver physiology, 305(10), G678-G684 (2013-09-28)
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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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