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Details

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
Structure of CEFTAZIDIME ANHYDROUS

SMILES

[H+].CC(C)(O\N=C(/C(=O)N[C@H]1[C@H]2SCC(C[N+]3=CC=CC=C3)=C(N2C1=O)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

HIDE SMILES / InChI

Molecular Formula C22H22N6O7S2
Molecular Weight 546.576
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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

PubMed

PubMed

TitleDatePubMed
Relative efficacies of broad-spectrum cephalosporins for treatment of methicillin-susceptible Staphylococcus aureus experimental infective endocarditis.
1993 Mar
Efficacy of cefepime in a Staphylococcus aureus endocarditis rat model.
1993 Nov
Neurotoxicity associated with intraperitoneal ceftazidime therapy in a CAPD patient.
1994
Ceftazidime-related nonconvulsive status epilepticus.
1994 Mar 14
[Convulsions associated with the administration of excessive dose of ceftazidime in patients with renal failure].
1994 Sep-Oct
[Acute interstitial nephritis. Role of ceftazidime].
1996
Mania due to clarithromycin therapy in a patient who was not infected with human immunodeficiency virus.
1996 Mar
[Analysis of the etiologic structure of urinary tract infection and antibiotic-resistance of its pathogens].
1997
QT prolongation and Torsades de Pointes associated with clarithromycin.
1998 Apr
[Basic and clinical studies on tazobactam/piperacillin in pediatric field].
1998 Jun
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Investigation of the effects of some drugs and phenolic compounds on human dihydrofolate reductase activity.
2015 Mar
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
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: Intravenous; Intramuscular
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Tue Mar 06 11:35:42 UTC 2018
Edited
by admin
on Tue Mar 06 11:35:42 UTC 2018
Record UNII
DZR1ENT301
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFTAZIDIME ANHYDROUS
Common Name English
1-(((6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)PYRIDINIUM HYDROXIDE INNER SALT 7(SUP 2)-(Z)-(O-(1-CARBOXY-1-METHYLETHYL)OXIME)
Common Name English
1-(((6R,7R)-7-(((2Z)-(2-AMINO-4-THIAZOLYL)((1-CARBOXY-1-METHYLETHOXY)IMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)PYRIDINIUM INNER SALT
Common Name English
PYRIDINIUM, 1-(((6R,7R)-7-(((2Z)-(2-AMINO-4-THIAZOLYL)((1-CARBOXY-1-METHYLETHOXY)IMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-, INNER SALT
Common Name English
PYRIDINIUM, 1-((7-(((2-AMINO-4-THIAZOLYL)((1-CARBOXY-1-METHYLETHOXY)IMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-, HYDROXIDE, INNER SALT, (6R-(6.ALPHA.,7.BETA.(Z)))-
Common Name English
CEFTAZIDIME [WHO-DD]
Common Name English
CEFTAZIDIME [INN]
Common Name English
CEFTAZIDIME [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
WHO-ATC J01DD02
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000175488
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
LIVERTOX 171
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
Code System Code Type Description
INN
4886
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY
CAS
72558-82-8
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY
EVMPD
SUB07422MIG
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY
MERCK INDEX
M3218
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY Merck Index
RXCUI
1545984
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY RxNorm
ECHA (EC/EINECS)
276-715-9
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY
NCI_THESAURUS
C90827
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY
EVMPD
SUB115175
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY
EPA CompTox
72558-82-8
Created by admin on Tue Mar 06 11:35:42 UTC 2018 , Edited by admin on Tue Mar 06 11:35:42 UTC 2018
PRIMARY
Related Record Type Details
SUBSTANCE->BASIS OF STRENGTH
Related Record Type Details
ACTIVE MOIETY