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C6895

Sigma-Aldrich

Cefaclor

Synonym(s):

7-(D-2-Amino-2-phenylacetamido)-3-chloro-3-cephem-4-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C15H14ClN3O4S
CAS Number:
53994-73-3
Molecular Weight:
367.81
Beilstein:
8176092
EC Number:
258-909-5
MDL number:
MFCD00151471
UNSPSC Code:
51283701
PubChem Substance ID:
24278331
NACRES:
NA.85

form

powder or crystals

solubility

soluble (slightly soluble in water, practically insoluble in methanol, ethanol)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

SMILES string

N[C@@H](C(=O)N[C@H]1[C@H]2SCC(Cl)=C(N2C1=O)C(O)=O)c3ccccc3

InChI

1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1

InChI key

QYIYFLOTGYLRGG-GPCCPHFNSA-N

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General description

Chemical structure: ß-lactam

Application

Cefaclor has been used in the heterologous expression of AaOr7 and AaOr8 in Xenopus laevis oocytes. It has also been used in cultures of isolated trigeminal ganglion (TG) and dorsal root ganglion (DRG) neurons.
Cefaclor is used to study urinary tract, intra-abdominal, and Haemophilus influenzae infections . It is used to study the mechanism of human renal organic anion and peptide transporters such as hOAT1, hPEPT1, and hPEPT2 and to study the effects of inhibition of penicillin-binding proteins on bacterial cell wall mucopeptide synthesis .

Biochem/physiol Actions

Cefaclor is a second generation cephalosporin with broad spectrum activity against Gram-negative and Gram-positive bacteria. It binds to penicillin-binding proteins and thereby inhibits the cell wall synthesis causing cell death.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Slightly soluble in water, practically insoluble in methanol, chloroform and benzene.

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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C O Onyeji et al.
Antimicrobial agents and chemotherapy, 38(5), 1112-1117 (1994-05-01)
The duration of time that serum drug levels remain above the MIC (time above the MIC) for the pathogen has been shown to be the most significant parameter determining the efficacies of beta-lactam antibiotics. In the described study, we investigated
Kiran Singh et al.
European journal of medicinal chemistry, 42(3), 394-402 (2007-01-17)
A few (1:1) and (1:2) metal complexes of cobalt(II), nickel(II), copper(II) and zinc(II) have been isolated with ligand derived from the condensation of 4-amino-3-mercapto-6-methyl-5-oxo-1,2,4-triazine with 2-acetylpyridine (L(1)) and characterized by elemental analysis, conductivity measurements, infrared, electronic, (1)H NMR spectral data
Meng Li et al.
Drug metabolism and disposition: the biological fate of chemicals, 34(4), 547-555 (2006-01-26)
Amoxicillin and cefaclor are two of the widely used beta-lactam antibiotics in the treatment of urinary tract infections. Both drugs are eliminated mainly by the kidney and rely on renal excretion to exert their antibacterial activities in the urinary tract.
C A Webster et al.
The Journal of antimicrobial chemotherapy, 38(1), 59-66 (1996-07-01)
Insusceptibility levels of cefaclor and other commonly prescribed antibiotics were determined for 489 consecutive hospital and community-associated urinary tract isolates of Escherichia coli from the Nottingham area of the UK. Significant resistance (MIC of > or = 8 mg/L) to
Nikita B Ruparel et al.
Journal of endodontics, 38(10), 1372-1375 (2012-09-18)
Regenerative endodontic procedures are an alternative treatment for immature teeth with necrotic pulps. Typically, intracanal medicaments such as triple antibiotic paste (TAP) or double antibiotic paste (DAP) and calcium hydroxide (Ca[OH](2)) are used for disinfection. However, their effect on human
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