Stereochemistry | ABSOLUTE |
Molecular Formula | C22H21N6O7S2.H |
Molecular Weight | 546.576 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H+].[H][C@]12SCC(C[N+]3=CC=CC=C3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC(C)(C)C([O-])=O)\C4=CSC(N)=N4)C([O-])=O
InChI
InChIKey=ORFOPKXBNMVMKC-DWVKKRMSSA-N
InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1
Ceftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic, used especially for Pseudomonas and other gram-negative infections in debilitated patients. Ceftazidime is used to treat lower respiratory tract, skin, urinary tract, blood-stream, joint, and abdominal infections, and meningitis. The drug is given intravenously (IV) or intramuscularly (IM) every 8–12 hours (two or three times a day), with dose and frequency varying by the type of infection, severity, and/or renal function of the patient. Injectable formulations of ceftazidime are currently nebulized "off-label" to manage Cystic Fibrosis, non-Cystic Fibrosis bronchiectasis, drug-resistant nontuberculous mycobacterial infections, ventilator-associated pneumonia, and post-transplant airway infections. Ceftazidime is generally well-tolerated. When side effects do occur, they are most commonly local effects from the intravenous line site, allergic reactions, and gastrointestinal symptoms. According to one manufacturer, in clinical trials, allergic reactions including itching, rash, and fever, happened in fewer than 2% of patients. Rare but more serious allergic reactions, such as toxic epidermal necrolysis, Stevens-Johnson syndrome, and erythema multiforme, have been reported with this class of antibiotics, including ceftazidime. Gastrointestinal symptoms, including diarrhea, nausea, vomiting, and abdominal pain, were reported in fewer than 2% of patients.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
Tox targets
Sourcing
PubMed
Patents
Sample Use Guides
The usual adult dosage is 1 gram administered intravenously or intramuscularly every 8 to 12 hours. The dosage and route should be determined by the susceptibility of the causative organisms, the severity of infection, and the condition and renal function of the patient.
Route of Administration:
Other
Ceftazidime–avibactam and comparator antibacterial agents were tested by reference broth microdilution against 417non-repetitive Gram-negative bacilli (387 unselected, plus 30selected blaKPC-positive, meropenem – nonsusceptible, Kleb-siella pneumoniae) collected prospectively from medical centersat Hospital das Clínicas da Faculdade de Medicina da Uni-versidade de São Paulo, Brazil, in 2014 and 2015. Minimum inhibitory concentrations (MICs), one per isolate, were determined by reference Clinical and Laboratory Standards Institute (CLSI) broth microdilution methods using frozen microtiter plates pre-loaded with antibiotic-containing growth medium. MICs ofceftazidime–avibactam were measured by varying the concen-tration of ceftazidime in twofold increments with avibactamat a fixed concentration of 4 mg/L. Addition of avibactam at 4 mg/L decreased MICs of cef-tazidime against unselected Enterobacteriaceae, especially K.pneumoniae, Citrobacter freundii, and Enterobacter cloacae, among which MIC90values decreased from 128 to >128 mg/L to0.5–4 mg/L. Among the unselected isolates of these three species 37–73% were susceptible to ceftazidime, whereas 100%were susceptible to ceftazidime–avibactam.
ACTIVE MOIETY
SALT/SOLVATE (PARENT)