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SML0037

Sigma-Aldrich

Ceftibuten hydrate

≥98% (HPLC)

Synonym(s):

(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate

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About This Item

Empirical Formula (Hill Notation):
C15H14N4O6S2 · xH2O
CAS Number:
97519-39-6
Molecular Weight:
410.42 (anhydrous basis)
MDL number:
MFCD20488049
UNSPSC Code:
51284115
PubChem Substance ID:
329825107
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: ≥50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

O.Nc1nc(cs1)\C(=C\CC(O)=O)C(=O)N[C@H]2[C@H]3SCC=C(N3C2=O)C(O)=O

InChI

1S/C15H14N4O6S2.H2O/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19;/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25);1H2/b6-1-;/t10-,13-;/m1./s1

InChI key

JMLVKZRNRBPPDZ-TXOBIQCCSA-N

General description

Chemical structure: ß-lactam

Biochem/physiol Actions

Ceftibuten is a β-lactam antibiotic with antibacterial activity. It is effective for mild-to-moderate respiratory infections. It displays high stability against extended-spectrum β-lactamases producing bacteria.
Ceftibuten is a third generation cephalosporin antibiotic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Masaki Kobayashi et al.
Biochimica et biophysica acta, 1715(1), 19-24 (2005-08-10)
Nateglinide, a novel oral hypoglycemic agent, possesses a carbonyl group and a peptide-type bond in its structure. We previously reported that nateglinide transport occurs via a single system that may be identical to the ceftibuten/H(+) cotransport system by the rat
Shirou Itagaki et al.
The Journal of pharmacology and experimental therapeutics, 312(1), 77-82 (2004-08-19)
(-)-N-(trans-4-Isopropylcyclohexanecarbonyl)-D-phenylalanine (nateglinide) is a novel oral hypoglycemic agent possessing a carboxyl group and a peptide-type bond in its structure. Although nateglinide quickly reaches the maximal serum concentration after oral administration, nateglinide itself is not transported by PepT1 or MCT1. The
R M Menon et al.
Biopharmaceutics & drug disposition, 24(7), 299-308 (2003-10-02)
Ceftibuten uptake into Caco-2 cells and intestinal brush border membrane vesicles is mediated by the dipeptide transport system (PEPT1). The apical to basolateral transport characteristics of ceftibuten across Caco-2 cells and rat jejunum mounted on a modified Ussing chamber was
Branka Bedenic et al.
Chemotherapy, 52(6), 293-297 (2006-09-30)
In this investigation, the urine samples obtained in a single oral-dose pharmacokinetic study were examined for their bactericidal activity against a range of relevant urinary tract pathogens. Six healthy volunteers received a single oral dose of ten oral antibiotics available
Miyako Okamura et al.
Pharmaceutical research, 20(9), 1389-1393 (2003-10-22)
The aim of this study was to examine the effects of zinc on the intestinal peptide transporters (PEPT1 and basolateral peptide transporter) and to elucidate the mechanism of the interactions. Caco-2 cells were pretreated with zinc, and the uptake studies
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