U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H12N8O4S3
Molecular Weight 440.481
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFTEZOLE

SMILES

[H][C@]12SCC(CSC3=NN=CS3)=C(N1C(=O)[C@H]2NC(=O)CN4C=NN=N4)C(O)=O

InChI

InChIKey=DZMVCVMFETWNIU-LDYMZIIASA-N
InChI=1S/C13H12N8O4S3/c22-7(1-20-4-14-18-19-20)16-8-10(23)21-9(12(24)25)6(2-26-11(8)21)3-27-13-17-15-5-28-13/h4-5,8,11H,1-3H2,(H,16,22)(H,24,25)/t8-,11-/m1/s1

HIDE SMILES / InChI

Molecular Formula C13H12N8O4S3
Molecular Weight 440.481
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ceftezole sodium is a cephalosporin antibiotic. Ceftezole was found to be a broad-spectrum antibiotic, active in vitro against many species of gram-positive and gram-negative bacteria except Pseudomonas aeruginosa, Serratia marcescens and Proteus vulgaris. Ceftezole sodium is used as an injectable or through an intravenous mode of delivery. The bactericidal activity of ceftezole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). The PBPs are transpeptidases which are vital in peptidoglycan biosynthesis. Therefore, their inhibition prevents this vital cell wall component from being properly synthesized. Ceftezole has been shown to exhibit potent alpha-glucosidase inhibitory activity. In in vitro alpha-glucosidase assays, ceftezole was shown to be a reversible, non-competitive inhibitor of yeast alpha-glucosidase with a Ki value of 5.78 x 10(-7) M when the enzyme mixture was pretreated with ceftezole. Ceftezole is used for the treatment of susceptible bacterial infections including septicemia, respiratory, biliary or GU tract, skin and skin structure, endocarditis. Surgical prophylaxis.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.1 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Ceftezole sodium for injection
Curative
Ceftezole sodium for injection
Curative
Ceftezole sodium for injection
Curative
Ceftezole sodium for injection

Cmax

ValueDoseCo-administeredAnalytePopulation
73.5 μg/mL
2 g single, intravenous
CEFTEZOLE serum
Homo sapiens
100.7 μg/mL
2 g single, intravenous
CEFTEZOLE serum
Homo sapiens
135.4 μg/mL
2 g single, intravenous
CEFTEZOLE serum
Homo sapiens
146.7 μg/mL
2 g single, intravenous
CEFTEZOLE serum
Homo sapiens
22.5 μg/mL
1 g single, intramuscular
CEFTEZOLE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.64 h
2 g single, intravenous
CEFTEZOLE serum
Homo sapiens
1.06 h
2 g single, intravenous
CEFTEZOLE serum
Homo sapiens
7.389 h
2 g single, intravenous
CEFTEZOLE serum
Homo sapiens
10.73 h
2 g single, intravenous
CEFTEZOLE serum
Homo sapiens
1.5 h
1 g single, intramuscular
CEFTEZOLE serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
IM 2-4 g/day in 2-3 divided doses.
Route of Administration: Intramuscular
In Vitro Use Guide
Susceptibilities of 48 clinical isolates of S. aureus to ceftezole showed a peak at 0.20 ug/ml and no resistant strain with an MIC of 3.13 ug/ml or above was observed.
Substance Class Chemical
Record UNII
2Z86SYP11W
Record Status Validated (UNII)
Record Version